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Methyl salicylate

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390: 239: 57: 1201: 72: 48: 743: 35: 850: 1074: 3573: 3593: 3583: 925: 853: 855: 1331:, due to its similar chemical and physical properties, in restoring (at least temporarily) the elastomeric properties of old rubber rollers, especially in printers, as a transfer agent in printmaking (to release toner from photocopied images and apply them to other surfaces), and as a penetrating oil to loosen rusted parts. 854: 1092:. Methyl salicylate is believed to function by being metabolized to the plant hormone salicylic acid. Since methyl salicylate is volatile, these signals can spread through the air to distal parts of the same plant or even to neighboring plants, whereupon they can function as a mechanism of 1315:
when excess pigments obscure structures or block light in the tissue being examined. This clearing generally only takes a few minutes, but the tissue must first be dehydrated in alcohol. It has also been discovered that methyl salicylate works as a
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lbs). The lowest published lethal dose is 101 mg/kg body weight in adult humans, (or 7.07 grams for a 70 kg adult). It has proven fatal to small children in doses as small as 4 mL. A seventeen-year-old
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Most instances of human toxicity due to methyl salicylate are a result of overapplication of topical analgesics, especially involving children. Salicylate, the major metabolite of methyl salicylate, may accumulate in
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Many plants produce methyl salicylate in small quantities. Methyl salicylate levels are often upregulated in response to biotic stress, especially infection by pathogens, where it plays a role in the induction of
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Some plants produce methyl salicylate in larger quantities, where it likely involved in direct defense against predators or pathogens. Examples of this latter class include: some species of the genus
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died in April 2007 after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products (using multiple patches against the manufacturer's instructions).
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Cordeiro, G. D.; Fernandes dos Santos, I. G.; da Silva, C. I.; Schlindwein, C.; Alves-dos-Santos, I.; Dötterl, S. (2019). "Nocturnal floral scent profiles of Myrtaceae fruit crops".
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g). Toxic ingestions of salicylates typically occur with doses of approximately 150 mg/kg body weight. This can be achieved with 1 mL of oil of wintergreen, which equates to 140
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Cooperband, Miriam F.; Wickham, Jacob; Cleary, Kaitlin; Spichiger, Sven-Erik; Zhang, Longwa; Baker, John; Canlas, Isaiah; Derstine, Nathan; Carrillo, Daniel (2019-03-21).
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for study, which apparently gather the chemical to synthesize pheromones, and to clear plant or animal tissue samples of color, and as such is useful for microscopy and
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solution. A single teaspoon (5 mL) of methyl salicylate contains approximately 6 g of salicylate, which is equivalent to almost twenty 300 mg
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Methyl salicylate is potentially deadly, especially for young children who may accidentally ingest preparations containing methyl salicylate, such as an
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Bartlet-Hunt, S. L.; Knappe, D. R. U.; Barlaz, M. A. (2008). "A Review of Chemical Warfare Agent Simulants for the Study of Environmental Behaviour".
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Knudsen, J. T.; Tollsten, L. (1993). "Trends in floral scent chemistry in pollination syndromes: floral scent composition in moth-pollinated taxa".
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James, D. G.; Price, T. S. (2004). "Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops".
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Altman, J. S.; Tyrer, N. M. (1980). "Filling selected neurons with cobalt through cut axons". In Strausfeld, N. J.; Miller, T. A. (eds.).
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Scully, F. E.; Hoigné, J. (January 1987). "Rate constants for reactions of singlet oxygen with phenols and other compounds in water".
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Shulaev, V.; Silverman, P.; Raskin, I. (1997). "Airborne signalling by methyl salicylate in plant pathogen resistance".
2239:"Discovery of three kairomones in relation to trap and lure development for spotted lanternfly (Hemiptera: Fulgoridae)" 1377: 17: 8231: 404: 945: 8186: 7499: 4768: 2346: 1180:. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of 1653: 1608: 1031: 8073: 7494: 7489: 6939: 1906: 704: 7474: 7469: 6416: 1926: 1554: 1400:
which may help professionals to confirm a diagnosis of poisoning in hospitalized patients or to assist in an
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Additional applications include: used as a simulant or surrogate for the research of chemical warfare agent
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in a dark room. When crushed, sugar crystals emit light; methyl salicylate amplifies the spark because it
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Schiestl, F. P.; Roubik, D. W. (2004). "Odor Compound Detection in Male Euglossine Bees".
1584:"The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information" 1583: 1004:
called "minty", as it is an ingredient in mint candies. It is produced by many species of
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Mason, L.; Moore, R. A.; Edwards, J. E.; McQuay, H. J.; Derry, S.; Wiffen, P. J. (2004).
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light and re-emitting it in the visible spectrum. It is used as an antiseptic in
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Boullard, Olivier; Leblanc, Henri; Besson, Bernard (2012). "Salicylic Acid".
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indicates initially developed first-in-class compound of specific group;
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Methyl salicylate is used in low concentrations (0.04% and under) as a
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Except where otherwise noted, data are given for materials in their
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washes, and treated with methyl salicylate to make the surrounding
1177: 1149: 1144: 1043: 836: 295: 829: 155: 8133: 7998: 7964: 7933: 7897: 7755: 7737: 7657: 7614: 7554: 7522: 7332: 7233: 7184: 7157: 7149: 7096: 7030: 6846: 6822: 6743: 6692: 6581: 6444: 6204: 6015: 5782: 5309: 5262: 5207: 4753: 3699: 3654: 3487: 3088: 2901: 2850: 2794: 2486:"Muscle-Pain Reliever Is Blamed For Staten Island Runner's Death" 2347:"Image Transfer & Rubbing Techniques – Reframing Photography" 1401: 1344: 1215: 1204: 1139: 1115:, the wintergreen or eastern teaberry; some species of the genus 993: 785: 605: 521: 307: 2236: 7925: 7901: 7859: 7759: 7687: 7526: 7508: 7366: 7327: 7322: 7100: 7086: 6831: 6747: 6642: 6633: 6623: 6602: 6565: 6536: 6531: 6470: 6462: 6448: 6425: 5965: 5166: 3028: 1239: 1207: 187: 3607: 2399:(10th ed.). New York, NY: McGraw-Hill. pp. 915–922. 7929: 7665: 7661: 7618: 7532: 7301: 7168: 7145: 6785: 6662: 6545: 6476: 5777: 1389: 1307:
Methyl salicylate is also used as a bait for attracting male
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Harvey, E. N. (1939). "The luminescence of sugar wafers".
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to various products and as an odor-masking agent for some
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CNN – Medical examiner: Sports cream caused teen's death
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Critical Reviews in Environmental Science and Technology
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to stain the skeleton, then cleansed with two or three
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Methyl salicylate is used in high concentrations as a
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InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
2619:
NLM Hazardous Substances Databank – Methyl salicylate
1886: 1147:, also called the meadowsweets; species of the genus 1049:
The biosynthesis of methyl salicylate arises via the
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Methyl salicylate was first isolated (from the plant
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InChI=1/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
6366: 2111:"Why do Wint-O-Green Life Savers spark in the dark?" 3908: 3851: 3800: 1658:"Sur quelques réactions du salicylate de méthylène" 274: 5189: 4331: 4216: 4139: 4032: 1660:[On some reactions of methyl salicylate]. 771: 4014: 3833: 2425:University of Oxford Department of Chemistry MSDS 1550:"Determination of Methyl Salicylate in Root Beer" 8198: 6110: 6091: 6046: 4488: 1000:(in which it is used as a flavoring), but often 996:liquid with a sweet, fruity odor reminiscent of 319: 2517:Disposition of Toxic Drugs and Chemicals in Man 2322:"MG Chemicals – Rubber Renue Safety Data Sheet" 1925:. Medicine.ox.ac.uk. 2003-05-26. Archived from 1816: 1157:. Methyl salicylate can also be a component of 1012:. It is also produced synthetically, used as a 852: 131: 6152: 2540:The British Pharmacopoeia Secretariat (2009). 2168: 2043: 2041: 1890:Ullmann's Encyclopedia of Industrial Chemistry 1019: 6350: 6129: 4585: 3786: 3623: 2639: 4713: 1509: 1137:, the black birch; all species of the genus 909:452.7 °C (846.9 °F; 725.8 K) 2221: 2038: 1449: 1447: 1445: 8207:Commercialization of traditional medicines 6364: 6357: 6343: 3793: 3779: 3630: 3616: 2646: 2632: 2421:"Safety (MSDS) data for methyl salicylate" 1773: 1543: 1541: 813: 540:−8.6 °C (16.5 °F; 264.5 K) 388: 237: 215: 8237:Substances discovered in the 19th century 2254: 2190: 2144:"Original Listerine Antiseptic Mouthwash" 2021: 1972: 1707: 1567: 355: 2601:MedlinePlus – Methyl salicylate overdose 1819:Botanical Journal of the Linnean Society 1442: 1320:that attracts some insects, such as the 1199: 1164: 1072: 2394: 1652: 1607: 1538: 1489: 1487: 1485: 1483: 1481: 1479: 1273:, for example by crushing Wint-O-Green 1069:Methyl salicylate as a plant metabolite 384: 14: 8199: 5184: 2514: 2066: 1995: 1547: 1334: 228: 6537:CS gas (2-chlorobenzal malononitrile) 6338: 3774: 3611: 2655:Non-steroidal anti-inflammatory drugs 2627: 2150:from the original on 17 February 2015 2138: 1169:Methyl salicylate can be produced by 1125:, particularly those in the subgenus 1034:(1813–1891), who identified it as an 895:96 °C (205 °F; 369 K) 550:222 °C (432 °F; 495 K) 416:Key: OSWPMRLSEDHDFF-UHFFFAOYSA-N 195: 175: 5807:Selective COX-2 inhibitors (coxibs): 3582: 2614:Wayback machine link to this article 2533: 2496:from the original on 18 January 2018 2226:. Springer-Verlag. pp. 373–402. 1689: 1619:[Investigations into the oil of 1548:Markus, John R. (13 February 2020). 1476: 1407: 8109:N-(p-Amylcinnamoyl)anthranilic acid 7225:N-(p-Amylcinnamoyl)anthranilic acid 6965:N-(p-Amylcinnamoyl)anthranilic acid 3916:Tooltip Prostaglandin D2 receptor 2 3859:Tooltip Prostaglandin D2 receptor 1 3233:COX-inhibiting nitric oxide donator 2606:MedlinePlus – Sports cream overdose 2397:Goldfrank's Toxicologic Emergencies 2371:"Salicylate Poisoning – Patient UK" 1192:(eastern teaberry or wintergreen). 426:Key: OSWPMRLSEDHDFF-UHFFFAOYAD 310: 294: 24: 5778:AM-404 (N-arachidonoylaminophenol) 5596:Anthranilic acids (fenamic acids): 5248:Mesalazine (5-aminosalicylic acid) 4339:Tooltip Prostaglandin EP4 receptor 4224:Tooltip Prostaglandin EP3 receptor 4147:Tooltip Prostaglandin EP2 receptor 4040:Tooltip Prostaglandin EP1 receptor 2344: 1831:10.1111/j.1095-8339.1993.tb00340.x 1788:10.1023/B:JOEC.0000042072.18151.6f 848: 55: 46: 25: 8248: 6268:γ-Linolenic acid (gamolenic acid) 5614:Meclofenamic acid (meclofenamate) 4023:Tooltip Prostaglandin E2 receptor 3842:Tooltip Prostaglandin D2 receptor 2594: 2345:Modrak, Rebekah and Bill Anthes. 1923:"Topical analgesics introduction" 6323:Leukotriene signaling modulators 6115:Tooltip Prostaglandin F synthase 6096:Tooltip Prostaglandin E synthase 6055:Tooltip Prostaglandin D synthase 4497:Tooltip Prostaglandin F receptor 3591: 3581: 3572: 3571: 2466:from the original on 29 Dec 2016 1030:) in 1843 by the French chemist 923: 741: 474: 70: 33: 5634:Talinflumic acid (talinflumate) 5624:Morniflumic acid (morniflumate) 5604:Floctafenic acid (floctafenate) 5587:Tiaprofenic acid (tiaprofenate) 3637: 3483:Superoxide dismutase / orgotein 2580:from the original on 2013-02-17 2566: 2508: 2478: 2442: 2413: 2388: 2377:from the original on 2015-08-18 2363: 2338: 2314: 2279: 2230: 2215: 2162: 2132: 2121:from the original on 2007-08-17 2103: 2060: 1989: 1940: 1915: 1880: 1858:10.1016/j.phytochem.2019.03.011 1837: 1825:(3). Oxford Academic: 263–284. 1810: 1767: 1672:from the original on 2015-11-25 1635:from the original on 2015-11-24 1590:from the original on 2019-12-06 1465:from the original on 2014-05-24 919:(at 25 °C , 100 kPa). 6157:Tooltip Thromboxane A synthase 5208:Aspirin (acetylsalicylic acid) 4422:16,16-Dimethyl Prostaglandin E 2795:Aspirin (acetylsalicylic acid) 2243:Journal of Economic Entomology 1724: 1692:"Phenylpropanoid Biosynthesis" 1683: 1646: 1601: 1576: 1503: 705:Occupational safety and health 480: 468: 13: 1: 8183:Receptor/signaling modulators 6532:CR gas (dibenzoxazepine; DBO) 6316:Receptor/signaling modulators 6138:Tooltip Prostacyclin synthase 5639:Tolfenamic acid (tolfenamate) 5609:Flufenamic acid (flufenamate) 5599:Etofenamic acid (etofenamate) 4655:Prostacyclin (prostaglandin I 4594:Tooltip Prostacyclin receptor 1555:Journal of AOAC International 1436: 1363:mg/kg of salicylates for a 10 596:Miscible in organic solvents 4722:Tooltip Thromboxane receptor 2427:. 2010-09-15. Archived from 2373:. Patient.info. 2011-04-20. 2351:www.reframingphotography.com 1532:10.1016/0045-6535(87)90004-X 1094:plant-to-plant communication 1061:followed by reaction with a 1032:Auguste André Thomas Cahours 7: 7811:Paracetamol (acetaminophen) 6719:Paracetamol (acetaminophen) 6589:Farnesyl thiosalicylic acid 6417:15-Deoxy-Δ-prostaglandin J2 5788:Paracetamol (acetaminophen) 5619:Mefenamic acid (mefenamate) 5273:Salicylate (salicylic acid) 2861:Salicylic acid (salicylate) 2171:Journal of Chemical Ecology 1965:10.1136/bmj.38040.607141.EE 1776:Journal of Chemical Ecology 1613:"Recherches sur l'huile de 1424: 1020:Biosynthesis and occurrence 101:Salicylic acid methyl ester 42: 10: 8253: 5467:Bucloxic acid (blucloxate) 5385:Indometacin (indomethacin) 2224:Neuroanatomical Techniques 2089:10.1126/science.90.2324.35 1289:mouthwash produced by the 1016:and as a flavoring agent. 8176: 7979: 7452: 7441: 7421: 7398: 7387: 7359: 7310: 7299: 7177: 7013: 7002: 6927: 6881: 6870: 6810: 6389: 6378: 6307: 6252: 6150: 6127: 6108: 6089: 6044: 5629:Niflumic acid (niflumate) 5182: 5165: 4940: 4733:Carbocyclic thromboxane A 4711: 4583: 4486: 4411: 4329: 4214: 4137: 4030: 4012: 3906: 3849: 3831: 3814: 3645: 3567: 3544: 3496: 3415: 3333: 3246: 3082: 3027: 2874: 2784: 2674: 2300:10.1080/10643380701643650 913: 722: 702: 697: 455: 435: 400: 115: 95: 83: 78: 69: 41: 32: 8232:Sweet-smelling chemicals 6796:Umbellularia californica 5947:Menatetrenone (vitamin K 5770:Aminophenols (anilines): 3531:Naproxen/diphenhydramine 2014:10.1136/bmj.328.7446.998 1899:10.1002/14356007.a23_477 780:Precautionary statements 89:Methyl 2-hydroxybenzoate 7766:N-Arachidonoyl dopamine 7548:Andrographis paniculata 6273:Dihomo-γ-linolenic acid 5670:Enolic acids (oxicams): 5213:Benorilate (benorylate) 3740:2-Ethylhexyl salicylate 3552:WHO-Essential Medicines 2183:10.1023/A:1021932131526 2002:British Medical Journal 1953:British Medical Journal 1893:. Weinheim: Wiley-VCH. 1569:10.1093/jaoac/57.4.1002 1195: 661:Magnetic susceptibility 8187:Ion channel modulators 7916:Tetrahydrocannabivarin 7411:Tripterygium wilfordii 6777:Tetrahydrocannabiorcol 6072:selenium tetrachloride 2880:and related substances 1996:Tramer, M. R. (2004). 1419:Japanese Pharmacopoeia 1223: 1210:that was treated with 1084: 859: 60: 51: 7744:Lysophosphatidic acid 5741:Aminonicotinic acids: 3735:Salicylmethylecgonine 3685:Bismuth subsalicylate 3536:Naproxen/esomeprazole 3526:Meloxicam/bupivacaine 3521:Ibuprofen/paracetamol 3511:Ibuprofen/hydrocodone 1621:Gaultheria procumbens 1615:Gaultheria procumbens 1414:British Pharmacopoeia 1293:company. It provides 1291:Johnson & Johnson 1203: 1189:Gaultheria procumbens 1165:Commercial production 1112:Gaultheria procumbens 1080:Gaultheria procumbens 1076: 1027:Gaultheria procumbens 992:. It is a colorless, 858: 552:Decomposes at 340–350 59: 50: 8124:Pregnenolone sulfate 7945:Euphorbia resinifera 7887:Euphorbia resinifera 7816:Phenylacetylrinvanil 7776:N-Oleoylethanolamide 7724:Homodihydrocapsaicin 7112:Pregnenolone sulfate 6975:Pregnenolone sulfate 6782:Thiopropanal S-oxide 6767:Tetrahydrocannabinol 6455:Allyl isothiocyanate 5390:Indometacin farnesil 5243:Magnesium salicylate 4874:Pinane thromboxane A 4635:Iloprost (ciloprost) 4255:Iloprost (ciloprost) 4061:Iloprost (ciloprost) 3760:Potassium salicylate 3725:Trolamine salicylate 3680:Isopropyl salicylate 3670:Magnesium salicylate 3506:Ibuprofen/famotidine 2964:Indometacin farnesil 2836:Magnesium salicylate 2657:(NSAIDs) (primarily 2576:. Moldb.nihs.go.jp. 2450:"Methyl Salicyclate" 2395:Hoffman, R. (2015). 1431:Trolamine salicylate 1374:cross-country runner 1313:immunohistochemistry 1077:Wintergreen plants ( 984:. It is the methyl 841:(fire diamond) 85:Preferred IUPAC name 8029:Cannabigerolic acid 7791:Nordihydrocapsaicin 7752:(acidic conditions) 5218:Carbasalate calcium 3516:Ibuprofen/oxycodone 3433:Chondroitin sulfate 2811:Carbasalate calcium 2515:Baselt, R. (2008). 2081:1939Sci....90...35N 1745:1997Natur.385..718S 1524:1987Chmsp..16..681S 1455:"Methyl salicylate" 1335:Safety and toxicity 563:Solubility in water 498: g/mol 29: 8227:3-Hydroxypropenals 7992:Vernonia tweediana 7571:African blue basil 7543:Bisandrographolide 7129:Steviol glycosides 7082:Hydroxycitronellal 6828:Dehydroligustilide 6648:Angelica acutiloba 6562:Dehydroligustilide 6080:selenium disulfide 5712:4-Aminoquinolines: 3423:Aminopropionitrile 2256:10.1093/jee/toy412 2192:20.500.11850/57276 2053:2018-03-19 at the 1378:Notre Dame Academy 1322:spotted lanternfly 1224: 1186:(sweet birch) and 1085: 972:with the formula C 962:oil of wintergreen 946:Infobox references 860: 104:Oil of wintergreen 61: 52: 28:Methyl salicylate 27: 18:Oil of wintergreen 8222:Salicylate esters 8194: 8193: 8172: 8171: 8104:Meclofenamic acid 7910:melegueta peppers 7781:Nonivamide (PAVA) 7517:melegueta peppers 7437: 7436: 7383: 7382: 7295: 7294: 7215:Meclofenamic acid 7138:Stevia rebaudiana 6998: 6997: 6960:Meclofenamic acid 6866: 6865: 6756:melegueta peppers 6729:Phenacyl chloride 6684:N-Methylmaleimide 6674:Methyl salicylate 6619:Hydrogen peroxide 6572:Diallyl disulfide 6434:melegueta peppers 6332: 6331: 6248: 6247: 5283:Sodium salicylate 5253:Methyl salicylate 5176: 5161: 5160: 4482: 4481: 4008: 4007: 3825: 3768: 3767: 3755:Copper aspirinate 3750:Benzyl salicylate 3690:Sodium salicylate 3665:Methyl salicylate 3605: 3604: 3453:Glycosaminoglycan 3303:Meclofenamic acid 2866:Sodium salicylate 2841:Methyl salicylate 2526:978-0-9626523-7-0 2406:978-0-07-180184-3 1739:(6618): 718–721. 1709:10.1093/mp/ssp106 1690:Vogt, T. (2010). 1654:Cahours, A. A. T. 1609:Cahours, A. A. T. 1498:Methyl salicylate 1494:Sigma-Aldrich Co. 1408:Compendial status 1271:triboluminescence 1244:counterirritation 1063:methyltransferase 958:Methyl salicylate 954:Chemical compound 952: 951: 766:Hazard statements 506:Colorless liquid 369:CompTox Dashboard 157:Interactive image 65: 64: 16:(Redirected from 8244: 8039:Cannabigerovarin 7771:N-Oleoyldopamine 7677:Euodia ruticarpa 7643:Dihydrocapsaicin 7450: 7449: 7446: 7396: 7395: 7392: 7308: 7307: 7304: 7052:Cooling Agent 10 7011: 7010: 7007: 6879: 6878: 6875: 6397:4-Hydroxynonenal 6387: 6386: 6383: 6368: 6359: 6352: 6345: 6336: 6335: 6283:Arachidonic acid 6158: 6154: 6139: 6135: 6116: 6112: 6097: 6093: 6056: 6052: 5879:Others/unsorted: 5454:Propionic acids: 5435:Sulindac sulfide 5200:Salicylic acids: 5191: 5186: 5180: 5179: 5170: 4723: 4719: 4595: 4591: 4498: 4494: 4340: 4336: 4225: 4221: 4148: 4144: 4041: 4037: 4028: 4027: 4024: 4020: 3917: 3913: 3860: 3856: 3847: 3846: 3843: 3839: 3829: 3828: 3819: 3795: 3788: 3781: 3772: 3771: 3675:Ethyl salicylate 3632: 3625: 3618: 3609: 3608: 3595: 3585: 3584: 3575: 3574: 3335:COX-2 inhibitors 3250:-arylanthranilic 3217:Tiaprofenic acid 2648: 2641: 2634: 2625: 2624: 2589: 2588: 2586: 2585: 2570: 2564: 2563: 2561: 2559: 2554:on 11 April 2009 2553: 2547:. Archived from 2546: 2542:"Index, BP 2009" 2537: 2531: 2530: 2512: 2506: 2505: 2503: 2501: 2492:. 10 June 2007. 2482: 2476: 2475: 2473: 2471: 2465: 2454: 2446: 2440: 2439: 2437: 2436: 2417: 2411: 2410: 2392: 2386: 2385: 2383: 2382: 2367: 2361: 2360: 2358: 2357: 2342: 2336: 2335: 2333: 2327:. Archived from 2326: 2318: 2312: 2311: 2283: 2277: 2276: 2258: 2234: 2228: 2227: 2219: 2213: 2212: 2194: 2166: 2160: 2159: 2157: 2155: 2136: 2130: 2129: 2127: 2126: 2107: 2101: 2100: 2064: 2058: 2045: 2036: 2035: 2025: 1993: 1987: 1986: 1976: 1944: 1938: 1937: 1935: 1934: 1919: 1913: 1912: 1884: 1878: 1877: 1841: 1835: 1834: 1814: 1808: 1807: 1782:(8): 1613–1628. 1771: 1765: 1764: 1753:10.1038/385718a0 1728: 1722: 1721: 1711: 1687: 1681: 1680: 1678: 1677: 1650: 1644: 1643: 1641: 1640: 1605: 1599: 1598: 1596: 1595: 1580: 1574: 1573: 1571: 1562:(4): 1002–1004. 1545: 1536: 1535: 1507: 1501: 1491: 1474: 1473: 1471: 1470: 1451: 1370: 1366: 1362: 1358: 1354: 1350: 1234:in deep heating 970:organic compound 936: 930: 927: 926: 880: 873: 866: 851: 831: 827: 823: 819: 815: 811: 807: 803: 799: 795: 791: 787: 773: 745: 680:Refractive index 673: 671: 635: 631: 617: 613: 585: 581: 575: 571: 555: 529: 497: 482: 476: 470: 463:Chemical formula 447:O=C(OC)c1ccccc1O 393: 392: 377: 375: 359: 323: 312: 298: 278: 249: 241: 230: 219: 199: 179: 159: 135: 74: 43: 37: 30: 26: 21: 8252: 8251: 8247: 8246: 8245: 8243: 8242: 8241: 8197: 8196: 8195: 8190: 8168: 8159:Tolfenamic acid 8079:Flufenamic acid 7975: 7882:Resiniferatoxin 7875:Ruta graveolens 7638:Diacyl glycerol 7433: 7417: 7379: 7375: 7355: 7341: 7291: 7277:Tolfenamic acid 7270:Ruta graveolens 7210:Flufenamic acid 7173: 7122:Ruta graveolens 7033:(intracellular) 6994: 6990:Tolfenamic acid 6945:Flufenamic acid 6923: 6899:Diacyl glycerol 6862: 6806: 6492:Cannabichromene 6402:4-Oxo-2-nonenal 6374: 6363: 6333: 6328: 6303: 6299: 6296:Prostaglandin H 6291: 6288:Prostaglandin G 6244: 6156: 6146: 6144:Tranylcypromine 6137: 6133: 6123: 6114: 6104: 6095: 6085: 6076:sodium selenite 6054: 6050: 6040: 5986:Rosmarinic acid 5950: 5758:Sulfonanilides: 5661:Oxyphenbutazone 5187: 5169: 5157: 4936: 4877: 4749: 4736: 4721: 4717: 4707: 4667: 4664:Prostaglandin E 4659:, epoprostenol) 4658: 4593: 4589: 4579: 4554: 4551:Prostaglandin F 4546: 4543:Prostaglandin D 4496: 4492: 4478: 4463: 4460:Prostaglandin F 4425: 4407: 4372: 4369:Prostaglandin E 4363: 4360:Prostaglandin E 4338: 4335: 4325: 4306:Ricinoleic acid 4295: 4292:Prostaglandin E 4286: 4283:Prostaglandin E 4278: 4275:Prostaglandin D 4223: 4220: 4210: 4180: 4177:Prostaglandin E 4171: 4168:Prostaglandin E 4146: 4143: 4133: 4093: 4090:Prostaglandin E 4084: 4081:Prostaglandin E 4039: 4036: 4022: 4018: 4004: 3935: 3932:Prostaglandin D 3915: 3912: 3902: 3873: 3870:Prostaglandin D 3858: 3855: 3841: 3837: 3818: 3810: 3799: 3769: 3764: 3641: 3636: 3606: 3601: 3563: 3556:withdrawn drugs 3540: 3498: 3492: 3411: 3337: 3329: 3325:Tolfenamic acid 3283:Flufenamic acid 3251: 3242: 3086: 3078: 3023: 2879: 2870: 2780: 2749:Oxyphenbutazone 2679: 2670: 2652: 2597: 2592: 2583: 2581: 2572: 2571: 2567: 2557: 2555: 2551: 2544: 2538: 2534: 2527: 2513: 2509: 2499: 2497: 2484: 2483: 2479: 2469: 2467: 2463: 2457:CAMEO Chemicals 2452: 2448: 2447: 2443: 2434: 2432: 2419: 2418: 2414: 2407: 2393: 2389: 2380: 2378: 2369: 2368: 2364: 2355: 2353: 2343: 2339: 2331: 2324: 2320: 2319: 2315: 2284: 2280: 2235: 2231: 2220: 2216: 2167: 2163: 2153: 2151: 2137: 2133: 2124: 2122: 2109: 2108: 2104: 2075:(2324): 35–36. 2065: 2061: 2055:Wayback Machine 2046: 2039: 1994: 1990: 1945: 1941: 1932: 1930: 1921: 1920: 1916: 1909: 1885: 1881: 1842: 1838: 1815: 1811: 1772: 1768: 1729: 1725: 1696:Molecular Plant 1688: 1684: 1675: 1673: 1651: 1647: 1638: 1636: 1606: 1602: 1593: 1591: 1582: 1581: 1577: 1546: 1539: 1508: 1504: 1492: 1477: 1468: 1466: 1453: 1452: 1443: 1439: 1427: 1410: 1368: 1364: 1360: 1356: 1352: 1348: 1337: 1299:organophosphate 1198: 1167: 1071: 1059:cytochrome P450 1022: 1008:, particularly 983: 979: 975: 966:wintergreen oil 955: 948: 943: 942: 941:  ?) 932: 928: 924: 920: 906: 903: 885: 884: 883: 882: 875: 868: 861: 857: 849: 782: 768: 754: 738: 715: 690: 688: 669: 667: 664: 650: 633: 629: 615: 611: 583: 579: 577: 573: 569: 565: 553: 551: 527: 495: 485: 479: 473: 465: 451: 448: 443: 442: 431: 428: 427: 424: 418: 417: 414: 408: 407: 396: 378: 371: 362: 342: 326: 313: 301: 281: 268: 259: 222: 202: 182: 162: 149: 138: 125: 111: 110: 91: 90: 23: 22: 15: 12: 11: 5: 8250: 8240: 8239: 8234: 8229: 8224: 8219: 8214: 8209: 8192: 8191: 8177: 8174: 8173: 8170: 8169: 8167: 8166: 8161: 8156: 8151: 8146: 8141: 8136: 8131: 8126: 8121: 8116: 8111: 8106: 8101: 8096: 8091: 8086: 8081: 8076: 8071: 8066: 8061: 8056: 8046: 8036: 8026: 8016: 8011: 8006: 8001: 7996: 7983: 7981: 7977: 7976: 7974: 7973: 7968: 7958: 7953: 7937: 7923: 7913: 7895: 7879: 7867: 7862: 7857: 7852: 7849:Dorrigo pepper 7842: 7828: 7821:Phorbol esters 7818: 7813: 7808: 7798: 7788: 7778: 7773: 7768: 7763: 7753: 7746: 7741: 7731: 7721: 7711: 7706: 7701: 7696: 7691: 7681: 7669: 7655: 7650: 7640: 7635: 7630: 7608: 7598: 7591:Cannabidivarin 7588: 7578: 7559:camphor laurel 7552: 7540: 7535: 7530: 7520: 7502: 7497: 7492: 7487: 7482: 7477: 7472: 7467: 7462: 7456: 7454: 7447: 7439: 7438: 7435: 7434: 7432: 7431: 7425: 7423: 7419: 7418: 7416: 7415: 7402: 7400: 7393: 7385: 7384: 7381: 7380: 7378: 7377: 7373: 7369: 7363: 7361: 7357: 7356: 7354: 7353: 7348: 7343: 7339: 7335: 7330: 7325: 7320: 7314: 7312: 7305: 7297: 7296: 7293: 7292: 7290: 7289: 7284: 7279: 7274: 7262: 7257: 7252: 7247: 7242: 7237: 7227: 7222: 7220:Mefenamic acid 7217: 7212: 7207: 7202: 7197: 7192: 7187: 7181: 7179: 7175: 7174: 7172: 7171: 7166: 7161: 7142: 7126: 7114: 7109: 7104: 7094: 7089: 7084: 7079: 7074: 7069: 7064: 7054: 7049: 7044: 7039: 7034: 7028: 7023: 7017: 7015: 7008: 7000: 6999: 6996: 6995: 6993: 6992: 6987: 6982: 6977: 6972: 6967: 6962: 6957: 6952: 6947: 6942: 6937: 6931: 6929: 6925: 6924: 6922: 6921: 6916: 6913:St John's wort 6906: 6901: 6896: 6893:St John's wort 6885: 6883: 6876: 6868: 6867: 6864: 6863: 6861: 6860: 6855: 6850: 6840: 6835: 6825: 6820: 6814: 6812: 6808: 6807: 6805: 6804: 6799: 6789: 6779: 6774: 6764: 6759: 6741: 6738:Dorrigo pepper 6731: 6726: 6721: 6716: 6706: 6696: 6686: 6681: 6671: 6666: 6659:Sichuan pepper 6652: 6636: 6631: 6629:Isothiocyanate 6626: 6621: 6616: 6611: 6606: 6596: 6591: 6586: 6574: 6569: 6559: 6549: 6539: 6534: 6529: 6522:Cinnamaldehyde 6519: 6509: 6499: 6489: 6484: 6479: 6474: 6452: 6442: 6437: 6419: 6414: 6409: 6404: 6399: 6393: 6391: 6384: 6376: 6375: 6362: 6361: 6354: 6347: 6339: 6330: 6329: 6327: 6326: 6319: 6312: 6308: 6305: 6304: 6302: 6301: 6297: 6293: 6289: 6285: 6280: 6278:Diacylglycerol 6275: 6270: 6265: 6256: 6254: 6250: 6249: 6246: 6245: 6243: 6242: 6237: 6232: 6227: 6222: 6217: 6212: 6207: 6202: 6197: 6192: 6187: 6182: 6177: 6172: 6167: 6161: 6159: 6148: 6147: 6142: 6140: 6131: 6125: 6124: 6119: 6117: 6106: 6105: 6100: 6098: 6087: 6086: 6084: 6083: 6065: 6059: 6057: 6048: 6042: 6041: 6039: 6038: 6033: 6028: 6023: 6018: 6013: 6008: 6003: 5998: 5993: 5988: 5983: 5978: 5973: 5968: 5963: 5958: 5953: 5948: 5944: 5939: 5934: 5929: 5924: 5919: 5914: 5909: 5904: 5899: 5894: 5889: 5884: 5872: 5867: 5862: 5857: 5852: 5847: 5842: 5837: 5832: 5827: 5822: 5817: 5812: 5800: 5795: 5790: 5785: 5780: 5775: 5763: 5751: 5746: 5734: 5722: 5717: 5705: 5700: 5695: 5690: 5685: 5680: 5675: 5666:Phenylbutazone 5663: 5658: 5653: 5648: 5636: 5631: 5626: 5621: 5616: 5611: 5606: 5601: 5589: 5584: 5579: 5574: 5569: 5564: 5559: 5554: 5549: 5544: 5539: 5534: 5529: 5524: 5519: 5514: 5509: 5504: 5499: 5494: 5489: 5484: 5479: 5474: 5469: 5464: 5459: 5447: 5442: 5437: 5432: 5427: 5422: 5417: 5412: 5407: 5402: 5397: 5392: 5387: 5382: 5377: 5372: 5367: 5362: 5357: 5352: 5347: 5342: 5337: 5332: 5327: 5322: 5317: 5312: 5307: 5302: 5297: 5285: 5280: 5275: 5270: 5265: 5260: 5255: 5250: 5245: 5240: 5235: 5230: 5225: 5220: 5215: 5210: 5205: 5196: 5194: 5177: 5163: 5162: 5159: 5158: 5156: 5155: 5150: 5145: 5140: 5135: 5130: 5125: 5120: 5115: 5110: 5105: 5100: 5095: 5090: 5085: 5080: 5075: 5070: 5065: 5060: 5055: 5050: 5045: 5040: 5035: 5030: 5025: 5020: 5015: 5010: 5005: 5000: 4995: 4990: 4985: 4980: 4975: 4970: 4965: 4960: 4955: 4950: 4944: 4942: 4938: 4937: 4935: 4934: 4929: 4924: 4919: 4914: 4909: 4904: 4899: 4894: 4889: 4884: 4879: 4875: 4871: 4866: 4861: 4856: 4851: 4846: 4841: 4836: 4831: 4826: 4821: 4816: 4811: 4806: 4801: 4796: 4791: 4786: 4781: 4776: 4771: 4762: 4761: 4756: 4751: 4747: 4743: 4738: 4734: 4726: 4724: 4715: 4709: 4708: 4706: 4705: 4696: 4695: 4690: 4685: 4680: 4675: 4670: 4665: 4661: 4656: 4652: 4647: 4642: 4640:Isocarbacyclin 4637: 4632: 4627: 4622: 4617: 4612: 4607: 4598: 4596: 4587: 4581: 4580: 4578: 4577: 4572: 4567: 4562: 4557: 4552: 4548: 4544: 4540: 4535: 4530: 4525: 4520: 4515: 4510: 4501: 4499: 4490: 4484: 4483: 4480: 4479: 4477: 4476: 4471: 4466: 4461: 4457: 4452: 4447: 4442: 4437: 4432: 4427: 4423: 4415: 4413: 4409: 4408: 4406: 4405: 4400: 4395: 4390: 4381: 4380: 4375: 4373:(dinoprostone) 4370: 4366: 4361: 4357: 4352: 4343: 4341: 4333: 4327: 4326: 4324: 4323: 4314: 4313: 4308: 4303: 4298: 4296:(dinoprostone) 4293: 4289: 4284: 4280: 4276: 4272: 4267: 4262: 4260:Isocarbacyclin 4257: 4252: 4247: 4242: 4237: 4228: 4226: 4218: 4212: 4211: 4209: 4208: 4203: 4198: 4189: 4188: 4183: 4181:(dinoprostone) 4178: 4174: 4169: 4165: 4160: 4151: 4149: 4141: 4135: 4134: 4132: 4131: 4126: 4121: 4116: 4111: 4102: 4101: 4096: 4094:(dinoprostone) 4091: 4087: 4082: 4078: 4073: 4068: 4063: 4058: 4053: 4044: 4042: 4034: 4025: 4016: 4010: 4009: 4006: 4005: 4003: 4002: 3997: 3992: 3987: 3982: 3977: 3972: 3967: 3962: 3957: 3952: 3947: 3938: 3937: 3933: 3929: 3920: 3918: 3910: 3904: 3903: 3901: 3900: 3895: 3890: 3881: 3880: 3875: 3871: 3863: 3861: 3853: 3844: 3835: 3826: 3812: 3811: 3798: 3797: 3790: 3783: 3775: 3766: 3765: 3763: 3762: 3757: 3752: 3747: 3742: 3737: 3732: 3727: 3722: 3717: 3712: 3707: 3702: 3697: 3692: 3687: 3682: 3677: 3672: 3667: 3662: 3657: 3652: 3650:Salicylic acid 3646: 3643: 3642: 3635: 3634: 3627: 3620: 3612: 3603: 3602: 3600: 3599: 3589: 3579: 3568: 3565: 3564: 3560:veterinary use 3545: 3542: 3541: 3539: 3538: 3533: 3528: 3523: 3518: 3513: 3508: 3502: 3500: 3494: 3493: 3491: 3490: 3485: 3480: 3475: 3470: 3465: 3460: 3455: 3450: 3445: 3440: 3435: 3430: 3425: 3419: 3417: 3413: 3412: 3410: 3409: 3404: 3399: 3394: 3389: 3384: 3379: 3374: 3369: 3364: 3359: 3347: 3341: 3339: 3331: 3330: 3328: 3327: 3322: 3317: 3312: 3309:Mefenamic acid 3305: 3300: 3295: 3290: 3285: 3280: 3275: 3270: 3265: 3259: 3257: 3244: 3243: 3241: 3240: 3229: 3224: 3219: 3214: 3209: 3204: 3199: 3194: 3189: 3184: 3179: 3172: 3167: 3162: 3157: 3152: 3147: 3140: 3135: 3130: 3125: 3120: 3115: 3110: 3105: 3100: 3094: 3092: 3084:propionic acid 3080: 3079: 3077: 3076: 3071: 3066: 3059: 3054: 3049: 3044: 3039: 3033: 3031: 3025: 3024: 3022: 3021: 3016: 3011: 3006: 3001: 2996: 2991: 2986: 2981: 2976: 2971: 2966: 2961: 2956: 2951: 2949:Fenclozic acid 2946: 2941: 2936: 2931: 2924: 2919: 2914: 2909: 2904: 2899: 2894: 2889: 2883: 2881: 2872: 2871: 2869: 2868: 2863: 2858: 2853: 2848: 2843: 2838: 2833: 2828: 2823: 2818: 2813: 2808: 2803: 2798: 2790: 2788: 2782: 2781: 2779: 2778: 2773: 2771:Sulfinpyrazone 2768: 2766:Propyphenazone 2763: 2760:Phenylbutazone 2756: 2751: 2746: 2741: 2736: 2731: 2726: 2721: 2716: 2711: 2706: 2701: 2696: 2691: 2689:Aminophenazone 2685: 2683: 2672: 2671: 2651: 2650: 2643: 2636: 2628: 2622: 2621: 2616: 2608: 2603: 2596: 2595:External links 2593: 2591: 2590: 2565: 2532: 2525: 2507: 2490:New York Times 2477: 2441: 2412: 2405: 2387: 2362: 2337: 2334:on 2015-06-26. 2313: 2294:(2): 112–136. 2278: 2249:(2): 671–682. 2229: 2214: 2177:(1): 253–257. 2161: 2131: 2102: 2059: 2037: 1988: 1939: 1914: 1907: 1879: 1846:Phytochemistry 1836: 1809: 1766: 1723: 1682: 1662:Comptes Rendus 1645: 1625:Comptes Rendus 1600: 1575: 1537: 1518:(4): 681–694. 1502: 1475: 1440: 1438: 1435: 1434: 1433: 1426: 1423: 1422: 1421: 1416: 1409: 1406: 1336: 1333: 1329:sulfur mustard 1212:methylene blue 1197: 1194: 1174:salicylic acid 1166: 1163: 1153:in the family 1143:in the family 1121:in the family 1105:in the family 1070: 1067: 1040:salicylic acid 1021: 1018: 990:salicylic acid 981: 977: 973: 953: 950: 949: 944: 922: 921: 917:standard state 914: 911: 910: 907: 900: 897: 896: 893: 887: 886: 876: 869: 862: 847: 846: 845: 844: 842: 833: 832: 806:P305+P351+P338 783: 778: 775: 774: 769: 764: 761: 760: 755: 750: 747: 746: 739: 734: 731: 730: 720: 719: 716: 713: 710: 709: 700: 699: 695: 694: 691: 686: 678: 675: 674: 672:10 cm/mol 665: 659: 656: 655: 652: 648: 638: 637: 626: 624:Vapor pressure 620: 619: 608: 598: 597: 594: 588: 587: 566: 561: 558: 557: 548: 542: 541: 538: 532: 531: 524: 518: 517: 514: 508: 507: 504: 500: 499: 493: 487: 486: 483: 477: 471: 466: 461: 458: 457: 453: 452: 450: 449: 446: 438: 437: 436: 433: 432: 430: 429: 425: 422: 421: 419: 415: 412: 411: 403: 402: 401: 398: 397: 395: 394: 381: 379: 367: 364: 363: 361: 360: 352: 350: 344: 343: 341: 340: 336: 334: 328: 327: 325: 324: 316: 314: 306: 303: 302: 300: 299: 291: 289: 283: 282: 280: 279: 271: 269: 264: 261: 260: 258: 257: 253: 251: 243: 242: 232: 224: 223: 221: 220: 212: 210: 204: 203: 201: 200: 192: 190: 184: 183: 181: 180: 172: 170: 164: 163: 161: 160: 152: 150: 143: 140: 139: 137: 136: 128: 126: 121: 118: 117: 113: 112: 109: 108: 105: 102: 98: 97: 93: 92: 88: 87: 81: 80: 76: 75: 67: 66: 63: 62: 53: 39: 38: 9: 6: 4: 3: 2: 8249: 8238: 8235: 8233: 8230: 8228: 8225: 8223: 8220: 8218: 8217:Methyl esters 8215: 8213: 8210: 8208: 8205: 8204: 8202: 8189: 8188: 8184: 8181: 8175: 8165: 8162: 8160: 8157: 8155: 8152: 8150: 8147: 8145: 8142: 8140: 8139:Ruthenium red 8137: 8135: 8132: 8130: 8127: 8125: 8122: 8120: 8119:Niflumic acid 8117: 8115: 8112: 8110: 8107: 8105: 8102: 8100: 8097: 8095: 8092: 8090: 8087: 8085: 8082: 8080: 8077: 8075: 8072: 8070: 8067: 8065: 8062: 8060: 8057: 8054: 8050: 8047: 8044: 8040: 8037: 8034: 8030: 8027: 8024: 8020: 8017: 8015: 8012: 8010: 8007: 8005: 8002: 8000: 7997: 7994: 7993: 7988: 7987:α-Spinasterol 7985: 7984: 7982: 7978: 7972: 7969: 7966: 7962: 7959: 7957: 7954: 7951: 7950: 7946: 7941: 7938: 7935: 7931: 7927: 7924: 7921: 7917: 7914: 7911: 7907: 7903: 7899: 7896: 7893: 7892: 7888: 7883: 7880: 7877: 7876: 7871: 7868: 7866: 7863: 7861: 7858: 7856: 7853: 7850: 7846: 7843: 7840: 7836: 7832: 7829: 7826: 7822: 7819: 7817: 7814: 7812: 7809: 7806: 7802: 7799: 7796: 7792: 7789: 7786: 7782: 7779: 7777: 7774: 7772: 7769: 7767: 7764: 7761: 7757: 7754: 7751: 7747: 7745: 7742: 7739: 7735: 7732: 7729: 7725: 7722: 7719: 7715: 7714:Homocapsaicin 7712: 7710: 7707: 7705: 7702: 7700: 7697: 7695: 7692: 7689: 7685: 7682: 7679: 7678: 7673: 7670: 7667: 7663: 7659: 7656: 7654: 7651: 7648: 7644: 7641: 7639: 7636: 7634: 7631: 7628: 7627:wild bergamot 7624: 7620: 7616: 7612: 7609: 7606: 7602: 7599: 7596: 7592: 7589: 7586: 7582: 7579: 7576: 7575:camphor basil 7572: 7568: 7564: 7560: 7556: 7553: 7550: 7549: 7544: 7541: 7539: 7536: 7534: 7531: 7528: 7524: 7521: 7518: 7514: 7510: 7506: 7503: 7501: 7498: 7496: 7493: 7491: 7488: 7486: 7483: 7481: 7478: 7476: 7473: 7471: 7468: 7466: 7463: 7461: 7458: 7457: 7455: 7451: 7448: 7445: 7440: 7430: 7429:Ruthenium red 7427: 7426: 7424: 7420: 7413: 7412: 7407: 7404: 7403: 7401: 7397: 7394: 7391: 7386: 7376: 7370: 7368: 7365: 7364: 7362: 7358: 7352: 7349: 7347: 7344: 7342: 7336: 7334: 7331: 7329: 7326: 7324: 7321: 7319: 7316: 7315: 7313: 7309: 7306: 7303: 7298: 7288: 7285: 7283: 7280: 7278: 7275: 7272: 7271: 7266: 7263: 7261: 7260:Ruthenium red 7258: 7256: 7253: 7251: 7248: 7246: 7243: 7241: 7240:Niflumic acid 7238: 7235: 7231: 7228: 7226: 7223: 7221: 7218: 7216: 7213: 7211: 7208: 7206: 7203: 7201: 7198: 7196: 7193: 7191: 7188: 7186: 7183: 7182: 7180: 7176: 7170: 7167: 7165: 7162: 7160:; indirectly) 7159: 7155: 7151: 7147: 7143: 7140: 7139: 7134: 7130: 7127: 7124: 7123: 7118: 7115: 7113: 7110: 7108: 7105: 7102: 7098: 7095: 7093: 7090: 7088: 7085: 7083: 7080: 7078: 7075: 7073: 7070: 7068: 7067:Frescolat MGA 7065: 7062: 7058: 7055: 7053: 7050: 7048: 7045: 7043: 7040: 7038: 7035: 7032: 7029: 7027: 7024: 7022: 7019: 7018: 7016: 7012: 7009: 7006: 7001: 6991: 6988: 6986: 6983: 6981: 6978: 6976: 6973: 6971: 6970:Niflumic acid 6968: 6966: 6963: 6961: 6958: 6956: 6953: 6951: 6948: 6946: 6943: 6941: 6938: 6936: 6933: 6932: 6930: 6926: 6920: 6917: 6914: 6910: 6907: 6905: 6902: 6900: 6897: 6894: 6890: 6887: 6886: 6884: 6880: 6877: 6874: 6869: 6859: 6858:Ruthenium red 6856: 6854: 6851: 6848: 6844: 6841: 6839: 6836: 6833: 6829: 6826: 6824: 6821: 6819: 6816: 6815: 6813: 6809: 6803: 6800: 6797: 6793: 6790: 6787: 6783: 6780: 6778: 6775: 6772: 6768: 6765: 6763: 6760: 6757: 6753: 6749: 6745: 6742: 6739: 6735: 6732: 6730: 6727: 6725: 6722: 6720: 6717: 6714: 6710: 6707: 6704: 6700: 6697: 6694: 6690: 6687: 6685: 6682: 6679: 6675: 6672: 6670: 6669:Methylglyoxal 6667: 6664: 6660: 6656: 6653: 6650: 6649: 6644: 6640: 6637: 6635: 6632: 6630: 6627: 6625: 6622: 6620: 6617: 6615: 6612: 6610: 6607: 6604: 6600: 6597: 6595: 6592: 6590: 6587: 6584: 6583: 6578: 6575: 6573: 6570: 6567: 6563: 6560: 6557: 6553: 6550: 6547: 6543: 6542:Cuminaldehyde 6540: 6538: 6535: 6533: 6530: 6527: 6523: 6520: 6517: 6513: 6510: 6507: 6503: 6500: 6497: 6493: 6490: 6488: 6485: 6483: 6480: 6478: 6475: 6472: 6468: 6464: 6460: 6456: 6453: 6450: 6446: 6443: 6441: 6438: 6435: 6431: 6427: 6423: 6420: 6418: 6415: 6413: 6410: 6408: 6405: 6403: 6400: 6398: 6395: 6394: 6392: 6388: 6385: 6382: 6377: 6373: 6370: 6360: 6355: 6353: 6348: 6346: 6341: 6340: 6337: 6325: 6324: 6320: 6318: 6317: 6313: 6310: 6309: 6306: 6300: 6294: 6292: 6286: 6284: 6281: 6279: 6276: 6274: 6271: 6269: 6266: 6264: 6263:Linoleic acid 6261: 6258: 6257: 6255: 6251: 6241: 6238: 6236: 6233: 6231: 6228: 6226: 6223: 6221: 6218: 6216: 6213: 6211: 6208: 6206: 6203: 6201: 6198: 6196: 6193: 6191: 6188: 6186: 6183: 6181: 6178: 6176: 6173: 6171: 6168: 6166: 6163: 6162: 6160: 6155: 6149: 6145: 6141: 6136: 6126: 6122: 6118: 6113: 6107: 6103: 6099: 6094: 6088: 6081: 6077: 6073: 6069: 6066: 6064: 6061: 6060: 6058: 6053: 6043: 6037: 6034: 6032: 6029: 6027: 6024: 6022: 6019: 6017: 6014: 6012: 6009: 6007: 6004: 6002: 5999: 5997: 5994: 5992: 5989: 5987: 5984: 5982: 5979: 5977: 5974: 5972: 5969: 5967: 5964: 5962: 5959: 5957: 5954: 5952: 5945: 5943: 5940: 5938: 5935: 5933: 5930: 5928: 5925: 5923: 5920: 5918: 5915: 5913: 5910: 5908: 5905: 5903: 5900: 5898: 5895: 5893: 5890: 5888: 5885: 5883: 5880: 5876: 5873: 5871: 5868: 5866: 5863: 5861: 5858: 5856: 5853: 5851: 5848: 5846: 5843: 5841: 5838: 5836: 5833: 5831: 5828: 5826: 5823: 5821: 5818: 5816: 5813: 5811: 5808: 5804: 5801: 5799: 5796: 5794: 5791: 5789: 5786: 5784: 5781: 5779: 5776: 5774: 5771: 5767: 5764: 5762: 5759: 5755: 5752: 5750: 5747: 5745: 5742: 5738: 5735: 5733: 5732:Fluproquazone 5730: 5729:Quinazolines: 5726: 5723: 5721: 5718: 5716: 5713: 5709: 5706: 5704: 5701: 5699: 5696: 5694: 5691: 5689: 5686: 5684: 5681: 5679: 5676: 5674: 5671: 5667: 5664: 5662: 5659: 5657: 5654: 5652: 5649: 5647: 5644: 5640: 5637: 5635: 5632: 5630: 5627: 5625: 5622: 5620: 5617: 5615: 5612: 5610: 5607: 5605: 5602: 5600: 5597: 5593: 5590: 5588: 5585: 5583: 5580: 5578: 5575: 5573: 5570: 5568: 5565: 5563: 5560: 5558: 5555: 5553: 5550: 5548: 5545: 5543: 5540: 5538: 5535: 5533: 5530: 5528: 5525: 5523: 5520: 5518: 5515: 5513: 5510: 5508: 5507:Flunoxaprofen 5505: 5503: 5500: 5498: 5495: 5493: 5492:Dexketoprofen 5490: 5488: 5487:Dexindoprofen 5485: 5483: 5480: 5478: 5475: 5473: 5470: 5468: 5465: 5463: 5460: 5458: 5455: 5451: 5448: 5446: 5443: 5441: 5438: 5436: 5433: 5431: 5428: 5426: 5425:Proglumetacin 5423: 5421: 5418: 5416: 5413: 5411: 5408: 5406: 5403: 5401: 5398: 5396: 5393: 5391: 5388: 5386: 5383: 5381: 5378: 5376: 5373: 5371: 5368: 5366: 5363: 5361: 5358: 5356: 5355:Difenpiramide 5353: 5351: 5348: 5346: 5343: 5341: 5338: 5336: 5333: 5331: 5328: 5326: 5323: 5321: 5318: 5316: 5313: 5311: 5308: 5306: 5303: 5301: 5298: 5296: 5293: 5292:Acetic acids: 5289: 5286: 5284: 5281: 5279: 5276: 5274: 5271: 5269: 5266: 5264: 5261: 5259: 5256: 5254: 5251: 5249: 5246: 5244: 5241: 5239: 5236: 5234: 5231: 5229: 5226: 5224: 5221: 5219: 5216: 5214: 5211: 5209: 5206: 5204: 5201: 5198: 5197: 5195: 5193: 5181: 5178: 5174: 5168: 5164: 5154: 5151: 5149: 5146: 5144: 5141: 5139: 5136: 5134: 5131: 5129: 5126: 5124: 5121: 5119: 5116: 5114: 5111: 5109: 5106: 5104: 5101: 5099: 5096: 5094: 5091: 5089: 5086: 5084: 5081: 5079: 5076: 5074: 5071: 5069: 5066: 5064: 5061: 5059: 5056: 5054: 5051: 5049: 5046: 5044: 5041: 5039: 5036: 5034: 5031: 5029: 5026: 5024: 5023:Fenprostalene 5021: 5019: 5016: 5014: 5011: 5009: 5006: 5004: 5001: 4999: 4996: 4994: 4991: 4989: 4986: 4984: 4981: 4979: 4976: 4974: 4973:Delprostenate 4971: 4969: 4966: 4964: 4961: 4959: 4956: 4954: 4951: 4949: 4946: 4945: 4943: 4939: 4933: 4930: 4928: 4925: 4923: 4920: 4918: 4915: 4913: 4910: 4908: 4905: 4903: 4900: 4898: 4895: 4893: 4890: 4888: 4885: 4883: 4880: 4878: 4872: 4870: 4867: 4865: 4862: 4860: 4857: 4855: 4852: 4850: 4847: 4845: 4842: 4840: 4837: 4835: 4832: 4830: 4827: 4825: 4822: 4820: 4817: 4815: 4812: 4810: 4807: 4805: 4802: 4800: 4797: 4795: 4792: 4790: 4787: 4785: 4782: 4780: 4777: 4775: 4772: 4770: 4767: 4764: 4763: 4760: 4757: 4755: 4752: 4750: 4746:Thromboxane A 4744: 4742: 4739: 4737: 4731: 4728: 4727: 4725: 4720: 4710: 4704: 4701: 4698: 4697: 4694: 4691: 4689: 4686: 4684: 4681: 4679: 4676: 4674: 4671: 4669: 4668:(alprostadil) 4662: 4660: 4653: 4651: 4648: 4646: 4643: 4641: 4638: 4636: 4633: 4631: 4628: 4626: 4623: 4621: 4618: 4616: 4613: 4611: 4608: 4606: 4603: 4600: 4599: 4597: 4592: 4582: 4576: 4573: 4571: 4568: 4566: 4563: 4561: 4558: 4556: 4549: 4547: 4541: 4539: 4536: 4534: 4531: 4529: 4526: 4524: 4521: 4519: 4516: 4514: 4511: 4509: 4506: 4503: 4502: 4500: 4495: 4485: 4475: 4472: 4470: 4467: 4465: 4458: 4456: 4453: 4451: 4448: 4446: 4443: 4441: 4438: 4436: 4433: 4431: 4428: 4426: 4420: 4417: 4416: 4414: 4410: 4404: 4401: 4399: 4396: 4394: 4391: 4389: 4386: 4383: 4382: 4379: 4376: 4374: 4367: 4365: 4364:(alprostadil) 4358: 4356: 4353: 4351: 4348: 4345: 4344: 4342: 4337: 4328: 4322: 4319: 4316: 4315: 4312: 4309: 4307: 4304: 4302: 4299: 4297: 4290: 4288: 4287:(alprostadil) 4281: 4279: 4273: 4271: 4268: 4266: 4263: 4261: 4258: 4256: 4253: 4251: 4248: 4246: 4243: 4241: 4238: 4236: 4233: 4230: 4229: 4227: 4222: 4213: 4207: 4204: 4202: 4199: 4197: 4194: 4191: 4190: 4187: 4184: 4182: 4175: 4173: 4172:(alprostadil) 4166: 4164: 4161: 4159: 4156: 4153: 4152: 4150: 4145: 4136: 4130: 4127: 4125: 4122: 4120: 4117: 4115: 4112: 4110: 4107: 4104: 4103: 4100: 4097: 4095: 4088: 4086: 4085:(alprostadil) 4079: 4077: 4074: 4072: 4069: 4067: 4064: 4062: 4059: 4057: 4054: 4052: 4049: 4046: 4045: 4043: 4038: 4029: 4026: 4021: 4011: 4001: 3998: 3996: 3993: 3991: 3988: 3986: 3983: 3981: 3978: 3976: 3973: 3971: 3968: 3966: 3963: 3961: 3958: 3956: 3953: 3951: 3948: 3946: 3943: 3940: 3939: 3936: 3930: 3928: 3925: 3922: 3921: 3919: 3914: 3905: 3899: 3896: 3894: 3891: 3889: 3886: 3883: 3882: 3879: 3876: 3874: 3868: 3865: 3864: 3862: 3857: 3848: 3845: 3840: 3830: 3827: 3823: 3817: 3813: 3809: 3806: 3803: 3796: 3791: 3789: 3784: 3782: 3777: 3776: 3773: 3761: 3758: 3756: 3753: 3751: 3748: 3746: 3743: 3741: 3738: 3736: 3733: 3731: 3728: 3726: 3723: 3721: 3718: 3716: 3713: 3711: 3708: 3706: 3703: 3701: 3698: 3696: 3693: 3691: 3688: 3686: 3683: 3681: 3678: 3676: 3673: 3671: 3668: 3666: 3663: 3661: 3658: 3656: 3653: 3651: 3648: 3647: 3644: 3640: 3633: 3628: 3626: 3621: 3619: 3614: 3613: 3610: 3598: 3594: 3590: 3588: 3580: 3578: 3570: 3569: 3566: 3561: 3557: 3553: 3549: 3543: 3537: 3534: 3532: 3529: 3527: 3524: 3522: 3519: 3517: 3514: 3512: 3509: 3507: 3504: 3503: 3501: 3495: 3489: 3486: 3484: 3481: 3479: 3476: 3474: 3471: 3469: 3466: 3464: 3461: 3459: 3456: 3454: 3451: 3449: 3446: 3444: 3443:Fluproquazone 3441: 3439: 3436: 3434: 3431: 3429: 3426: 3424: 3421: 3420: 3418: 3414: 3408: 3405: 3403: 3400: 3398: 3395: 3393: 3390: 3388: 3385: 3383: 3380: 3378: 3375: 3373: 3370: 3368: 3365: 3363: 3360: 3357: 3353: 3352: 3348: 3346: 3343: 3342: 3340: 3336: 3332: 3326: 3323: 3321: 3320:Niflumic acid 3318: 3316: 3313: 3311: 3310: 3306: 3304: 3301: 3299: 3296: 3294: 3291: 3289: 3286: 3284: 3281: 3279: 3276: 3274: 3271: 3269: 3266: 3264: 3261: 3260: 3258: 3255: 3249: 3245: 3239: 3235: 3234: 3230: 3228: 3225: 3223: 3220: 3218: 3215: 3213: 3210: 3208: 3205: 3203: 3200: 3198: 3195: 3193: 3190: 3188: 3185: 3183: 3180: 3178: 3177: 3173: 3171: 3168: 3166: 3163: 3161: 3158: 3156: 3153: 3151: 3148: 3146: 3145: 3141: 3139: 3136: 3134: 3133:Flunoxaprofen 3131: 3129: 3126: 3124: 3121: 3119: 3118:Dexketoprofen 3116: 3114: 3111: 3109: 3106: 3104: 3101: 3099: 3096: 3095: 3093: 3090: 3087:derivatives ( 3085: 3081: 3075: 3072: 3070: 3067: 3065: 3064: 3060: 3058: 3055: 3053: 3050: 3048: 3045: 3043: 3040: 3038: 3035: 3034: 3032: 3030: 3026: 3020: 3017: 3015: 3012: 3010: 3007: 3005: 3002: 3000: 2999:Proglumetacin 2997: 2995: 2994:Prodolic acid 2992: 2990: 2987: 2985: 2982: 2980: 2977: 2975: 2972: 2970: 2967: 2965: 2962: 2960: 2957: 2955: 2952: 2950: 2947: 2945: 2942: 2940: 2937: 2935: 2934:Difenpiramide 2932: 2930: 2929: 2925: 2923: 2920: 2918: 2915: 2913: 2910: 2908: 2905: 2903: 2900: 2898: 2895: 2893: 2890: 2888: 2885: 2884: 2882: 2877: 2873: 2867: 2864: 2862: 2859: 2857: 2854: 2852: 2849: 2847: 2844: 2842: 2839: 2837: 2834: 2832: 2829: 2827: 2824: 2822: 2819: 2817: 2814: 2812: 2809: 2807: 2804: 2802: 2799: 2797: 2796: 2792: 2791: 2789: 2787: 2783: 2777: 2774: 2772: 2769: 2767: 2764: 2762: 2761: 2757: 2755: 2752: 2750: 2747: 2745: 2742: 2740: 2737: 2735: 2732: 2730: 2727: 2725: 2722: 2720: 2717: 2715: 2712: 2710: 2707: 2705: 2702: 2700: 2697: 2695: 2692: 2690: 2687: 2686: 2684: 2682: 2681:pyrazolidines 2677: 2673: 2668: 2664: 2660: 2656: 2649: 2644: 2642: 2637: 2635: 2630: 2629: 2626: 2620: 2617: 2615: 2612: 2609: 2607: 2604: 2602: 2599: 2598: 2579: 2575: 2569: 2550: 2543: 2536: 2528: 2522: 2518: 2511: 2495: 2491: 2487: 2481: 2462: 2459:. June 1999. 2458: 2451: 2445: 2431:on 2011-06-07 2430: 2426: 2422: 2416: 2408: 2402: 2398: 2391: 2376: 2372: 2366: 2352: 2348: 2341: 2330: 2323: 2317: 2309: 2305: 2301: 2297: 2293: 2289: 2282: 2274: 2270: 2266: 2262: 2257: 2252: 2248: 2244: 2240: 2233: 2225: 2218: 2210: 2206: 2202: 2198: 2193: 2188: 2184: 2180: 2176: 2172: 2165: 2149: 2145: 2141: 2135: 2120: 2116: 2115:HowStuffWorks 2112: 2106: 2098: 2094: 2090: 2086: 2082: 2078: 2074: 2070: 2063: 2056: 2052: 2049: 2044: 2042: 2033: 2029: 2024: 2019: 2015: 2011: 2008:(7446): 998. 2007: 2003: 1999: 1992: 1984: 1980: 1975: 1970: 1966: 1962: 1959:(7446): 995. 1958: 1954: 1950: 1943: 1929:on 2012-08-04 1928: 1924: 1918: 1910: 1904: 1900: 1896: 1892: 1891: 1883: 1875: 1871: 1867: 1863: 1859: 1855: 1851: 1847: 1840: 1832: 1828: 1824: 1820: 1813: 1805: 1801: 1797: 1793: 1789: 1785: 1781: 1777: 1770: 1762: 1758: 1754: 1750: 1746: 1742: 1738: 1734: 1727: 1719: 1715: 1710: 1705: 1701: 1697: 1693: 1686: 1671: 1667: 1663: 1659: 1655: 1649: 1634: 1630: 1626: 1622: 1618: 1616: 1610: 1604: 1589: 1585: 1579: 1570: 1565: 1561: 1557: 1556: 1551: 1544: 1542: 1533: 1529: 1525: 1521: 1517: 1513: 1506: 1499: 1495: 1490: 1488: 1486: 1484: 1482: 1480: 1464: 1460: 1456: 1450: 1448: 1446: 1441: 1432: 1429: 1428: 1420: 1417: 1415: 1412: 1411: 1405: 1403: 1399: 1395: 1391: 1385: 1383: 1382:Staten Island 1379: 1375: 1346: 1342: 1341:essential oil 1332: 1330: 1325: 1323: 1319: 1314: 1310: 1305: 1303: 1300: 1296: 1292: 1288: 1284: 1280: 1276: 1272: 1268: 1264: 1260: 1256: 1251: 1249: 1245: 1241: 1237: 1233: 1229: 1221: 1217: 1213: 1209: 1206: 1202: 1193: 1191: 1190: 1185: 1184: 1179: 1175: 1172: 1162: 1160: 1159:floral scents 1156: 1152: 1151: 1146: 1142: 1141: 1136: 1135: 1130: 1129: 1124: 1120: 1119: 1114: 1113: 1108: 1104: 1103: 1097: 1095: 1091: 1082: 1081: 1075: 1066: 1064: 1060: 1056: 1052: 1051:hydroxylation 1047: 1045: 1041: 1037: 1033: 1029: 1028: 1017: 1015: 1011: 1007: 1003: 1002:associatively 999: 995: 991: 987: 971: 967: 963: 959: 947: 940: 935: 918: 912: 908: 905: 899: 898: 894: 892: 889: 888: 881: 874: 867: 843: 840: 839: 835: 834: 784: 781: 777: 776: 770: 767: 763: 762: 759: 756: 753: 749: 748: 744: 740: 737: 733: 732: 728: 726: 721: 717: 712: 711: 707: 706: 701: 696: 692: 685: 681: 677: 676: 666: 662: 658: 657: 653: 647: 643: 640: 639: 627: 625: 622: 621: 609: 607: 603: 600: 599: 595: 593: 590: 589: 567: 564: 560: 559: 549: 547: 546:Boiling point 544: 543: 539: 537: 536:Melting point 534: 533: 525: 523: 520: 519: 516:Sweet, rooty 515: 513: 510: 509: 505: 502: 501: 494: 492: 489: 488: 467: 464: 460: 459: 454: 445: 444: 441: 434: 420: 410: 409: 406: 399: 391: 387: 386:DTXSID5025659 383: 382: 380: 370: 366: 365: 358: 354: 353: 351: 349: 346: 345: 338: 337: 335: 333: 330: 329: 322: 318: 317: 315: 309: 305: 304: 297: 293: 292: 290: 288: 285: 284: 277: 273: 272: 270: 267: 263: 262: 255: 254: 252: 250: 245: 244: 240: 236: 233: 231: 229:ECHA InfoCard 226: 225: 218: 214: 213: 211: 209: 206: 205: 198: 194: 193: 191: 189: 186: 185: 178: 174: 173: 171: 169: 166: 165: 158: 154: 153: 151: 147: 142: 141: 134: 130: 129: 127: 124: 120: 119: 114: 106: 103: 100: 99: 94: 86: 82: 77: 73: 68: 58: 54: 49: 45: 44: 40: 36: 31: 19: 8179: 8178: 8019:Cannabigerol 7990: 7943: 7885: 7873: 7835:black pepper 7795:chili pepper 7728:chili pepper 7718:chili pepper 7709:Hepoxilin B3 7704:Hepoxilin A3 7675: 7647:chili pepper 7605:chili pepper 7546: 7409: 7268: 7195:Clotrimazole 7136: 7120: 7072:Frescolat ML 6980:Progesterone 6889:Adhyperforin 6802:WIN 55,212-2 6795: 6673: 6646: 6614:Hepoxilin B3 6609:Hepoxilin A3 6580: 6512:Cannabigerol 6321: 6314: 6259: 5878: 5806: 5803:Propacetamol 5793:Parapropamol 5769: 5757: 5740: 5728: 5720:Floctafenine 5711: 5669: 5646:Azapropazone 5643:Pyrazolones: 5642: 5595: 5577:Tarenflurbil 5512:Flurbiprofen 5482:Dexibuprofen 5462:Benoxaprofen 5457:Alminoprofen 5453: 5380:Glucametacin 5291: 5268:Salicylamide 5258:Salacetamide 5252: 5199: 5148:Trimoprostil 5143:Tiprostanide 5128:Spiriprostil 5063:Naxaprostene 5013:Esuberaprost 4968:Cobiprostone 4766:Antagonists: 4765: 4729: 4700:Antagonists: 4699: 4693:Treprostinil 4601: 4533:Fluprostenol 4523:Cloprostenol 4504: 4418: 4385:Antagonists: 4384: 4350:Lubiprostone 4346: 4318:Antagonists: 4317: 4231: 4193:Antagonists: 4192: 4186:Treprostinil 4154: 4106:Antagonists: 4105: 4071:Lubiprostone 4047: 3942:Antagonists: 3941: 3923: 3885:Antagonists: 3884: 3878:Treprostinil 3866: 3695:Salicylamide 3664: 3547: 3499:combinations 3349: 3315:Morniflumate 3307: 3278:Floctafenine 3263:Azapropazone 3247: 3231: 3207:Tarenflurbil 3192:Piketoprofen 3187:Pelubiprofen 3174: 3142: 3138:Flurbiprofen 3113:Dexibuprofen 3103:Benoxaprofen 3098:Alminoprofen 3061: 2926: 2856:Salicylamide 2840: 2793: 2758: 2734:Mofebutazone 2714:Famprofazone 2709:Difenamizole 2699:Azapropazone 2582:. Retrieved 2574:"NIHS Japan" 2568: 2556:. Retrieved 2549:the original 2535: 2516: 2510: 2498:. Retrieved 2489: 2480: 2468:. Retrieved 2456: 2444: 2433:. Retrieved 2429:the original 2424: 2415: 2396: 2390: 2379:. Retrieved 2365: 2354:. Retrieved 2350: 2340: 2329:the original 2316: 2291: 2287: 2281: 2246: 2242: 2232: 2223: 2217: 2174: 2170: 2164: 2152:. Retrieved 2134: 2123:. Retrieved 2105: 2072: 2068: 2062: 2057:at Drugs.com 2005: 2001: 1991: 1956: 1952: 1942: 1931:. Retrieved 1927:the original 1917: 1888: 1882: 1849: 1845: 1839: 1822: 1818: 1812: 1779: 1775: 1769: 1736: 1732: 1726: 1699: 1695: 1685: 1674:. Retrieved 1665: 1661: 1648: 1637:. Retrieved 1628: 1624: 1620: 1614: 1603: 1592:. Retrieved 1578: 1559: 1553: 1515: 1511: 1505: 1467:. Retrieved 1459:chemister.ru 1458: 1386: 1367:kg child (22 1338: 1326: 1306: 1281:, absorbing 1252: 1225: 1187: 1183:Betula lenta 1181: 1168: 1155:Polygalaceae 1148: 1138: 1133: 1127: 1116: 1110: 1109:, including 1100: 1098: 1086: 1078: 1055:benzoic acid 1048: 1025: 1023: 1010:wintergreens 965: 961: 957: 956: 902:Autoignition 837: 757: 724: 714:Main hazards 703: 683: 645: 332:RTECS number 197:ChEMBL108545 116:Identifiers 96:Other names 8154:Tivanisiran 8059:Capsazepine 7971:Zucapsaicin 7839:long pepper 7805:Pacific yew 7694:GSK1016790A 7581:Cannabidiol 7567:camphorweed 7255:RQ-00203078 7250:PF-05105679 7190:Capsazepine 6955:GSK2293017A 6919:Substance P 6904:GSK1702934A 6853:PF-04745637 6792:Umbellulone 6713:Pacific yew 6699:Oleocanthal 6678:wintergreen 6639:Ligustilide 6502:Cannabidiol 6467:horseradish 6260:Precursors: 6200:Nicogrelate 6180:Furegrelate 6121:Bimatoprost 6031:Trifenagrel 6021:Tiflamizole 5991:Rutecarpine 5976:Resveratrol 5917:Glimepiride 5882:Anitrazafen 5860:Robenacoxib 5840:Lumiracoxib 5773:Acetanilide 5715:Antrafenine 5673:Ampiroxicam 5567:Pranoprofen 5552:Naproxcinod 5445:Zidometacin 5370:Fenclofenac 5295:Aceclofenac 5233:Ethenzamide 5228:Dipyrocetyl 5123:Rosaprostol 5103:Posaraprost 5088:Penprostene 5078:Ornoprostil 5058:Mexiprostil 5053:Meteneprost 5008:Eptaloprost 4983:Dimoxaprost 4948:Arbaprostil 4902:Seratrodast 4794:BMS-180,291 4625:Carbacyclin 4575:Unoprostone 4555:(dinoprost) 4538:Latanoprost 4513:Bimatoprost 4508:Alfaprostol 4464:(dinoprost) 4403:ONO-AE3-208 4355:Misoprostol 4311:Sulprostone 4301:Remiprostol 4270:Misoprostol 4265:Latanoprost 4240:Carbacyclin 4201:PF-04418948 4163:Misoprostol 4099:Sulprostone 4076:Misoprostol 4066:Latanoprost 4000:Vidupiprant 3990:Timapiprant 3985:Setipiprant 3960:Fevipiprant 3927:Indometacin 3898:Vidupiprant 3893:Laropiprant 3715:Ethenzamide 3639:Salicylates 3448:Glucosamine 3428:Benzydamine 3397:Robenacoxib 3382:Lumiracoxib 3273:Etofenamate 3238:Naproxcinod 3227:Zaltoprofen 3037:Ampiroxicam 2959:Indometacin 2887:Aceclofenac 2878:derivatives 2876:acetic acid 2826:Ethenzamide 2821:Dipyrocetyl 2786:salicylates 2676:pyrazolones 2500:22 February 2048:Wintergreen 1852:: 193–198. 1631:: 853–856. 1512:Chemosphere 1355:g/mL = 5.87 1309:orchid bees 1283:ultraviolet 1275:Life Savers 1263:chewing gum 1228:rubefacient 1222:transparent 1171:esterifying 904:temperature 891:Flash point 752:Signal word 708:(OHS/OSH): 503:Appearance 456:Properties 235:100.003.925 177:CHEBI:31832 8201:Categories 8049:Cannabinol 7949:pooissonii 7940:Tinyatoxin 7891:pooissonii 7855:Probenecid 7845:Polygodial 7801:Paclitaxel 7785:PAVA spray 7672:Evodiamine 7623:pepperwort 7538:Anandamide 7505:α-Sanshool 7453:Activators 7406:Triptolide 7399:Activators 7311:Activators 7287:TRPM4-IN-5 7205:Elismetrep 7133:stevioside 7061:eucalyptus 7057:Eucalyptol 7021:ADP-ribose 7014:Activators 6950:GSK417651A 6909:Hyperforin 6882:Activators 6762:Tear gases 6734:Polygodial 6724:PF-4840154 6709:Paclitaxel 6577:Dicentrine 6487:Bradykinin 6422:α-Sanshool 6390:Activators 6372:modulators 6230:Samixogrel 6225:Rolafagrel 6210:Picotamide 6190:Midazogrel 6165:Camonagrel 6026:Timegadine 5971:Pamicogrel 5942:Licofelone 5922:Hyperforin 5887:Clobuzarit 5875:Valdecoxib 5870:Tilmacoxib 5855:Polmacoxib 5830:Etoricoxib 5798:Phenacetin 5766:Nimesulide 5744:Clonixeril 5737:Proquazone 5693:Lornoxicam 5592:Vedaprofen 5542:Miroprofen 5537:Loxoprofen 5532:Ketoprofen 5527:Indoprofen 5502:Fenoprofen 5415:Oxametacin 5410:Nabumetone 5350:Diclofenac 5345:Clometacin 5340:Cinmetacin 5335:Bumadizone 5315:Alclofenac 5300:Acemetacin 5238:Guacetisal 5223:Diflunisal 5173:inhibitors 5138:Tilsuprost 5118:Rivenprost 5113:Rioprostil 5108:Prostalene 5093:Pimilprost 5083:Oxoprostol 5073:Nocloprost 5048:Luprostiol 5038:Lanproston 5033:Froxiprost 5028:Flunoprost 5018:Etiproston 5003:Enisoprost 4998:Eganoprost 4958:Ciprostene 4927:Terutroban 4917:Sulotroban 4897:Samixogrel 4882:Ramatroban 4869:Picotamide 4854:Mipitroban 4849:Linotroban 4834:Imitrodast 4824:ICI-192605 4819:ICI-185282 4804:Domitroban 4784:Argatroban 4683:Taprostene 4605:ACT-333679 4570:Travoprost 4565:Tafluprost 4560:Sulotroban 4518:Carboprost 4474:Taprenepag 4455:Omidenepag 4450:Nocloprost 4440:Evatanepag 4435:Carboprost 4388:Grapiprant 3980:Ramatroban 3888:Asapiprant 3808:modulators 3802:Prostanoid 3730:Homosalate 3720:Diflunisal 3705:Benorilate 3478:Proquazone 3468:Nimesulide 3463:Nabumetone 3458:Hyperforin 3407:Valdecoxib 3372:Etoricoxib 3222:Vedaprofen 3170:Miroprofen 3165:Loxoprofen 3160:Ketoprofen 3155:Indoprofen 3128:Fenoprofen 3052:Lornoxicam 2989:Oxametacin 2928:Diclofenac 2922:Bumadizone 2897:Alclofenac 2892:Acemetacin 2831:Guacetisal 2816:Diflunisal 2806:Benorylate 2776:Suxibuzone 2744:Nifenazone 2729:Metamizole 2584:2013-07-01 2435:2023-04-24 2381:2013-07-01 2356:2021-09-07 2125:2008-04-27 1933:2012-11-07 1908:3527306730 1676:2013-11-19 1639:2013-11-19 1594:2019-12-03 1469:2014-05-23 1437:References 1351:mL × 1.174 1347:tablets (5 1302:pesticides 1279:fluoresces 1123:Betulaceae 1102:Gaultheria 1090:resistance 736:Pictograms 602:Solubility 592:Solubility 491:Molar mass 357:LAV5U5022Y 266:IUPHAR/BPS 208:ChemSpider 144:3D model ( 123:CAS Number 107:Betula oil 8180:See also: 8164:TRPV3-74a 8149:SB-705498 8144:SB-366791 8094:Lanthanum 8089:HC-067047 8009:Asivatrep 7870:Rutamarin 7734:Incensole 7684:Gingerols 7653:Estradiol 7629:, others) 7611:Carvacrol 7601:Capsaicin 7495:13-oxoODE 7485:12S-HpETE 7465:5',6'-EET 7265:Rutamarin 7164:Thio-BCTC 7117:Rutamarin 7047:Coolact P 6838:HC-030031 6703:olive oil 6599:Gingerols 6412:12S-HpETE 6235:Terbogrel 6215:Pirmagrel 6175:Dazoxiben 6170:Dazmegrel 6063:Retinoids 5981:Romazarit 5927:Itazigrel 5912:FR-122047 5907:Flumizole 5865:Rofecoxib 5850:Parecoxib 5845:Mavacoxib 5835:Firocoxib 5825:Deracoxib 5820:Cimicoxib 5815:Celecoxib 5810:Apricoxib 5761:Flosulide 5725:Glafenine 5708:Tenoxicam 5703:Piroxicam 5698:Meloxicam 5582:Tepoxalin 5562:Pirprofen 5557:Oxaprozin 5522:Ibuproxam 5517:Ibuprofen 5477:Carprofen 5472:Butibufen 5450:Zomepirac 5420:Oxindanac 5405:Mofezolac 5400:Lonazolac 5395:Ketorolac 5375:Fentiazac 5330:Bufexamac 5325:Bromfenac 5305:Aclofenac 5288:Triflusal 5278:Salsalate 5203:Aloxiprin 5153:Viprostol 5098:Piriprost 5068:Nileprost 5043:Limaprost 4993:Ecraprost 4988:Doxaprost 4978:Deprostil 4963:Clinprost 4922:Terbogrel 4912:SQ-29,548 4907:SQ-28,668 4864:ONO-11120 4829:Ifetroban 4799:Daltroban 4789:Bay U3405 4759:Vapiprost 4730:Agonists: 4703:RO1138452 4678:Selexipag 4673:Ralinepag 4630:Cicaprost 4620:BMY-45778 4615:Beraprost 4602:Agonists: 4528:Enprostil 4505:Agonists: 4469:Simenepag 4445:Gemeprost 4419:Agonists: 4393:GW-627368 4347:Agonists: 4250:Enprostil 4245:Cicaprost 4235:Beraprost 4232:Agonists: 4158:Butaprost 4155:Agonists: 4056:Enprostil 4051:Beraprost 4048:Agonists: 3955:Bay U3405 3924:Agonists: 3867:Agonists: 3805:signaling 3710:Salsalate 3660:Aloxiprin 3548:underline 3473:Oxaceprol 3438:Diacerein 3402:Rofecoxib 3392:Parecoxib 3387:Mavacoxib 3377:Firocoxib 3367:Deracoxib 3362:Cimicoxib 3356:+tramadol 3351:Celecoxib 3345:Apricoxib 3298:Glafenine 3293:Flutiazin 3254:fenamates 3212:Tepoxalin 3197:Pirprofen 3182:Oxaprozin 3150:Ibuproxam 3144:Ibuprofen 3108:Carprofen 3074:Tenoxicam 3069:Pivoxicam 3063:Piroxicam 3057:Meloxicam 3019:Zomepirac 2984:Mofezolac 2979:Lonazolac 2974:Ketorolac 2954:Fentiazac 2917:Bufexamac 2912:Bromfenac 2846:Salsalate 2801:Aloxiprin 2754:Phenazone 2719:Feprazone 2704:Clofezone 2265:0022-0493 2140:Listerine 1668:: 43–47. 1318:kairomone 1295:fragrance 1287:Listerine 1259:root beer 1257:agent in 1255:flavoring 1238:(such as 1236:liniments 1232:analgesic 1128:Betulenta 1107:Ericaceae 1014:fragrance 998:root beer 822:P337+P313 818:P332+P313 802:P302+P352 798:P301+P312 727:labelling 339:VO4725000 256:204-317-7 248:EC Number 8114:NGD-8243 8099:Mavatrep 8084:GRC-6211 8053:cannabis 8043:cannabis 8033:cannabis 8023:cannabis 8004:AMG-9810 7980:Blockers 7961:Vanillin 7956:Tramadol 7920:cannabis 7898:Shogaols 7831:Piperine 7595:cannabis 7585:cannabis 7563:rosemary 7480:12S-HETE 7475:9-oxoODE 7422:Blockers 7372:PI(4,5)P 7360:Blockers 7338:PI(3,5)P 7245:Ononetin 7230:Nicotine 7178:Blockers 7154:fructose 7146:tastants 7092:Linalool 7077:Geraniol 7037:CIM-0216 6928:Blockers 6843:Nicotine 6818:A-967079 6811:Blockers 6771:cannabis 6744:Shogaols 6689:Nicotine 6655:Linalool 6594:Formalin 6556:turmeric 6552:Curcumin 6526:cinnamon 6516:cannabis 6506:cannabis 6496:cannabis 6482:ASP-7663 6440:Acrolein 6311:See also 6220:Ridogrel 6195:Nafagrel 6185:Isbogrel 6068:Selenium 6036:Tropesin 6011:SC-58125 5996:Satigrel 5961:NCX-4040 5937:L-670596 5932:L-655240 5892:Curcumin 5754:Flunixin 5749:Clonixin 5688:Isoxicam 5683:Enolicam 5678:Droxicam 5656:Isopyrin 5651:Dipyrone 5572:Suprofen 5547:Naproxen 5497:Fenbufen 5440:Tolmetin 5430:Sulindac 5365:Felbinac 5360:Etodolac 5320:Bendazac 5133:Tiaprost 4953:Ataprost 4941:Unsorted 4887:Ridogrel 4859:ONO-3708 4844:L-670596 4839:L-655240 4814:GR-32191 4430:Aganepag 4412:Unsorted 4398:L-161982 4378:TCS-2510 4321:L-798106 4206:TG 4-155 4129:SC-51322 4124:SC-51089 4119:SC-19220 4114:ONO-8130 3950:AZD-1981 3945:ADC-3680 3816:Receptor 3745:Aluminon 3577:category 3338:(coxibs) 3288:Flunixin 3268:Clonixin 3202:Suprofen 3176:Naproxen 3123:Fenbufen 3047:Isoxicam 3042:Droxicam 3014:Tolmetin 3009:Tiopinac 3004:Sulindac 2969:Isoxepac 2944:Felbinac 2939:Etodolac 2907:Bendazac 2739:Morazone 2724:Kebuzone 2694:Ampyrone 2578:Archived 2494:Archived 2461:Archived 2375:Archived 2308:97484598 2273:30753676 2201:12647866 2154:25 March 2148:Archived 2119:Archived 2097:17798129 2051:Archived 2032:15105325 1983:15033879 1874:92997657 1866:30939396 1804:36124603 1796:15537163 1718:20035037 1702:: 2–20. 1670:Archived 1656:(1843). 1633:Archived 1611:(1843). 1588:Archived 1463:Archived 1425:See also 1178:methanol 1150:Polygala 1145:Rosaceae 1134:B. lenta 1131:such as 1065:enzyme. 1044:methanol 968:) is an 838:NFPA 704 718:Harmful 698:Hazards 663:(χ) 632:mmHg (54 217:13848808 133:119-36-8 8212:Flavors 8134:RN-9893 8129:RN-1734 7999:AMG-517 7965:vanilla 7934:oregano 7906:Sichuan 7884:(RTX) ( 7860:Protons 7823:(e.g., 7756:Menthol 7738:incense 7658:Eugenol 7615:oregano 7555:Camphor 7523:Allicin 7513:Sichuan 7500:20-HETE 7490:13-HODE 7333:ML2-SA1 7234:tobacco 7185:AMG-333 7158:sucrose 7150:glucose 7148:(e.g., 7131:(e.g., 7097:Menthol 7031:Calcium 6847:tobacco 6823:AM-0902 6752:Sichuan 6693:tobacco 6582:Lindera 6459:mustard 6445:Allicin 6430:Sichuan 6407:4,5-EET 6369:channel 6240:U63557A 6205:Ozagrel 6016:Tenidap 5956:NCX-466 5902:FK-3311 5897:DuP-697 5783:Bucetin 5310:Amfenac 5263:Salicin 4932:TRA-418 4779:AA-2414 4769:12-HETE 4754:U-46619 4688:TRA-418 4645:MRE-269 4196:AH-6809 4109:AH-6809 3995:TM30089 3975:QAV-680 3970:MK-7246 3965:MK-1029 3822:ligands 3700:Salicin 3655:Aspirin 3587:commons 3488:Tenidap 3252:acids ( 3089:profens 3029:oxicams 2902:Amfenac 2851:Salicin 2665:, also 2209:2845587 2077:Bibcode 2069:Science 1761:4370291 1741:Bibcode 1623:]. 1520:Bibcode 1402:autopsy 1345:aspirin 1220:tissues 1216:ethanol 1140:Spiraea 994:viscous 939:what is 937: ( 758:Warning 642:Acidity 614:g/g (30 606:acetone 582:g/L (30 572:g/L (21 522:Density 496:152.149 308:PubChem 8074:DHEA-S 7926:Thymol 7902:ginger 7825:4α-PDD 7688:ginger 7527:garlic 7509:ginger 7470:9-HODE 7367:ML-SI3 7328:ML-SA1 7323:MK6-83 7144:Sweet 7107:PMD 38 7087:Icilin 6940:DHEA-S 6832:celery 6748:ginger 6643:celery 6634:JT-010 6624:Icilin 6603:ginger 6566:celery 6471:wasabi 6463:radish 6449:garlic 6426:ginger 6253:Others 6102:HQL-79 6006:SC-560 6001:SC-236 5966:NS-398 5167:Enzyme 4809:EP-045 4774:13-APA 4714:TP (TX 4650:NS-304 4610:AFP-07 3597:portal 2558:5 July 2523:  2470:24 Apr 2403:  2306:  2271:  2263:  2207:  2199:  2095:  2030:  2023:404503 2020:  1981:  1974:404501 1971:  1905:  1872:  1864:  1802:  1794:  1759:  1733:Nature 1716:  1394:plasma 1369:  1365:  1361:  1357:  1353:  1349:  1240:Bengay 1208:embryo 1118:Betula 1006:plants 934:verify 931:  693:1.538 668:−8.630 634:  630:  616:  612:  584:  580:  574:  570:  554:  528:  440:SMILES 296:D01087 188:ChEMBL 79:Names 8064:DCDPC 7930:thyme 7666:clove 7662:basil 7619:thyme 7533:AM404 7460:2-APB 7346:SF-22 7318:EVP21 7302:TRPML 7200:DCDPC 7169:WS-12 6935:DCDPC 6786:onion 6663:thyme 6585:spp.) 6546:cumin 6477:AM404 4892:S-145 4741:I-BOP 4586:IP (I 4489:FP (F 4015:EP (E 3834:DP (D 3546:Key: 3497:NSAID 3416:other 2667:N02BA 2552:(PDF) 2545:(PDF) 2464:(PDF) 2453:(PDF) 2332:(PDF) 2325:(PDF) 2304:S2CID 2205:S2CID 1870:S2CID 1800:S2CID 1757:S2CID 1398:serum 1390:blood 1267:mints 1248:NSAID 1205:Chick 1176:with 1057:by a 1036:ester 986:ester 578:0.697 568:0.639 530:g/cm 526:1.174 405:InChI 168:ChEBI 146:JSmol 8069:DHEA 8014:BCTC 7908:and 7865:RhTx 7760:mint 7748:Low 7699:Heat 7633:DHEA 7515:and 7444:TRPV 7390:TRPP 7351:SN-2 7282:TPPO 7101:mint 7042:Cold 7026:BCTC 7005:TRPM 6985:Pyr3 6873:TRPC 6754:and 6432:and 6381:TRPA 6153:TXAS 6111:PGFS 6092:PGES 5190:PTGS 2663:M02A 2661:and 2659:M01A 2560:2009 2521:ISBN 2502:2017 2472:2023 2401:ISBN 2269:PMID 2261:ISSN 2197:PMID 2156:2015 2093:PMID 2028:PMID 1979:PMID 1903:ISBN 1862:PMID 1792:PMID 1714:PMID 1265:and 1230:and 1196:Uses 1042:and 830:P501 826:P362 814:P330 810:P321 794:P280 790:P270 786:P264 772:H302 654:9.8 636:°C) 618:°C) 610:10.1 586:°C) 512:Odor 348:UNII 321:4133 287:KEGG 276:2431 7135:) ( 6367:TRP 6130:PGI 6047:PGD 5185:COX 2296:doi 2251:doi 2247:112 2187:hdl 2179:doi 2085:doi 2018:PMC 2010:doi 2006:328 1969:PMC 1961:doi 1957:328 1895:doi 1854:doi 1850:162 1827:doi 1823:113 1784:doi 1749:doi 1737:385 1704:doi 1564:doi 1528:doi 1396:or 1380:on 1376:at 1053:of 1038:of 988:of 964:or 725:GHS 604:in 576:°C) 556:°C 374:EPA 311:CID 8203:: 8185:• 7932:, 7904:, 7837:, 7750:pH 7664:, 7625:, 7621:, 7617:, 7573:, 7569:, 7565:, 7561:, 7511:, 7156:, 7152:, 6750:, 6661:, 6645:, 6469:, 6465:, 6461:, 6428:, 6078:, 6074:, 5877:; 5805:; 5768:; 5756:; 5739:; 5727:; 5710:; 5668:; 5641:; 5594:; 5452:; 5290:; 4716:A2 4553:2α 4491:2α 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Index

Oil of wintergreen
Skeletal formula
Ball-and-stick model
Space-filling model
Sample of a clear liquid
Preferred IUPAC name
CAS Number
119-36-8
JSmol
Interactive image
ChEBI
CHEBI:31832
ChEMBL
ChEMBL108545
ChemSpider
13848808
ECHA InfoCard
100.003.925
Edit this at Wikidata
EC Number
IUPHAR/BPS
2431
KEGG
D01087
PubChem
4133
RTECS number
UNII
LAV5U5022Y
CompTox Dashboard

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