377:
228:
35:
44:
2233:
547:
803:
cannot deal with allicin’s mode of action and develop effective defence mechanism" and argue "that could be the key to sustainable drug design addressing serious problems with escalating emergence of multidrug-resistant bacterial strains".
724:
Alliinase is irreversibly deactivated below pH 3; as such, allicin is generally not produced in the body from the consumption of fresh or powdered garlic. Furthermore, allicin can be unstable, breaking down within 16 hours at 23 °C.
3976:
3112:
2847:
2269:
1102:
Rabinkov A, Miron T, Konstantinovski L, Wilchek M, Mirelman D, Weiner L (February 1998). "The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins".
3737:
2501:
2262:
1327:
Marchese A, Barbieri R, Sanches-Silva A, Daglia M, Nabavi SF, Jafari NJ, Izadi M, Ajami M, Nabavi SM (2016). "Antifungal and antibacterial activities of allicin: A review".
617:. It is also known as allyl thiosulfinate. Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.
598:
into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as
4164:
2255:
3455:
2740:
2474:
3683:
560:
1503:
Cavallito CJ, Bailey JH (1944). "Allicin, the
Antibacterial Principle of Allium sativum. I. Isolation, Physical Properties and Antibacterial Action".
2979:
2984:
4066:
3926:
2938:
2867:
629:
functional group, R-S-(O)-S-R. The compound is not present in garlic unless tissue damage occurs, and is formed by the action of the enzyme
3117:
426:
3921:
3782:
3177:
3076:
3029:
2959:
4026:
4041:
3019:
836:. These compounds are hydrophobic, easily pass from the intestines to the bloodstream, and are reduced to thiamine by cysteine or
1446:"Effect of physicochemical parameters on the stability and activity of garlic alliinase and its use for in-situ allicin synthesis"
3258:
3230:
2897:
3284:
3250:
1539:
1311:
264:
2278:
957:
Kourounakis PN, Rekka EA (November 1991). "Effect on active oxygen species of alliin and Allium sativum (garlic) powder".
4021:
3137:
2877:
1149:
761:
SOH), pyruvate, and ammonium ions. At room temperature, two molecules of allylsulfenic acid condense to form allicin.
4124:
1174:
795:
A study from 2021 has shown "a combination of the short half-life, high reactivity and non-specificity to particular
391:
2216:
1572:
555:
567:
4099:
3412:
1072:
Nikolic V, Stankovic M, Nikolic L, Cvetkovic D (January 2004). "Mechanism and kinetics of synthesis of allicin".
126:
34:
3986:
3407:
3402:
2852:
890:
43:
4134:
3387:
3382:
2329:
4095:
3372:
2933:
334:
223:
133:
355:
185:
1530:
Bettendorff L (2014). "Chapter 7 - Thiamine". In
Zempleni J, Suttie JW, Gregory JF, Stover PJ (eds.).
301:
235:
4159:
4139:
3487:
3397:
3392:
3377:
3194:
2694:
2324:
2319:
2199:
870:
770:
372:
295:
4119:
3678:
3460:
1627:
777:, but as of 2016, the safety and efficacy of allicin to treat infections in people was unclear.
3981:
3828:
3545:
3417:
3323:
2689:
2334:
2076:
1869:
1594:
785:
3656:
2113:
1645:
1444:
Janská P, Knejzlík Z, Perumal AS, Jurok R, Tokárová V, Nicolau DV, et al. (2021-03-19).
638:
583:
985:
4154:
4129:
4036:
3857:
3799:
3728:
3636:
3589:
3024:
2887:
2825:
2805:
2679:
2367:
2014:
1946:
1889:
1635:
1565:
1457:
923:
849:
813:
609:
Allicin is an oily, slightly yellow liquid that gives garlic its distinctive odor. It is a
343:
205:
56:
8:
3941:
3861:
3803:
3761:
3703:
3471:
2650:
2061:
1864:
1794:
1754:
821:
750:
102:
92:
1461:
1356:"Complementary and alternative medicine for prevention and treatment of the common cold"
927:
376:
227:
165:
3822:
3688:
3483:
3429:
2994:
2668:
2560:
2346:
2293:
2189:
1924:
1919:
1904:
1809:
1749:
1480:
1445:
1421:
1396:
1372:
1355:
1284:
1221:
1194:
1046:
1019:
935:
881:
145:
2029:
1115:
4016:
3539:
3127:
3050:
3041:
2872:
2641:
2596:
2586:
2531:
2484:
2284:
2184:
2081:
2051:
1899:
1879:
1839:
1824:
1819:
1774:
1769:
1759:
1744:
1535:
1485:
1426:
1377:
1307:
1226:
1170:
1145:
1119:
1081:
1051:
986:"Allicin and related compounds: Biosynthesis, synthesis and pharmacological activity"
966:
939:
650:
599:
1244:
Brodnitz MH, Pascale JV, Derslice LV (1971). "Flavor components of garlic extract".
788:
allicin (20 times the amount in a garlic clove) showed effectiveness to prevent the
3951:
3717:
3555:
2964:
2625:
2309:
2046:
2009:
1909:
1894:
1874:
1859:
1854:
1834:
1789:
1779:
1512:
1475:
1465:
1416:
1412:
1408:
1367:
1336:
1280:
1253:
1216:
1206:
1111:
1041:
1031:
1000:
931:
816:
and John Hays Bailey in 1944. Allicin was discovered as part of efforts to create
454:
1193:
Borlinghaus J, Albrecht F, Gruhlke MC, Nwachukwu ID, Slusarenko AJ (August 2014).
1018:
Borlinghaus J, Albrecht F, Gruhlke MC, Nwachukwu ID, Slusarenko AJ (August 2014).
323:
4149:
4144:
4071:
3991:
3794:
3787:
3189:
3182:
3122:
3034:
2902:
2857:
2404:
2314:
2236:
2194:
2004:
1829:
1804:
1784:
1739:
1558:
1470:
3818:
3733:
3503:
3425:
3132:
2664:
2571:
2541:
2434:
2342:
2148:
2091:
2086:
1951:
1914:
1884:
1849:
1844:
1814:
1799:
1677:
1650:
1340:
1211:
1036:
781:
538:
4113:
4051:
4031:
3626:
3341:
3172:
3152:
2882:
2770:
2581:
2454:
2371:
2153:
2105:
2071:
2066:
1983:
1971:
1764:
1712:
853:
833:
829:
626:
614:
526:
516:
216:
3931:
3747:
3707:
3640:
3630:
3621:
3616:
3559:
3517:
3107:
2892:
2801:
2714:
2526:
2521:
2424:
2143:
2138:
2118:
1687:
1660:
1489:
1430:
1381:
1230:
1085:
1055:
825:
733:
The biosynthesis of allicin commences with the conversion of cysteine into
606:, i.e. the defense mechanism against attacks by pests on the garlic plant.
1123:
1004:
970:
943:
3971:
3899:
3883:
3751:
3723:
3606:
3550:
3493:
3479:
3167:
3162:
3102:
2831:
2816:
2811:
2765:
2704:
2631:
2611:
2590:
2551:
2414:
2379:
2247:
2161:
2056:
2019:
1988:
1966:
1956:
1702:
1682:
1670:
984:
Ilic D, Nikolic V, Nikolic L, Stankovic M, Stanojevic L, Cakic M (2011).
861:
837:
789:
603:
1516:
1257:
3961:
3852:
3767:
3757:
3713:
3697:
3693:
3584:
3450:
3318:
3301:
3199:
3045:
2973:
2969:
2916:
2862:
2821:
2646:
2636:
2621:
2489:
2399:
2133:
2123:
1978:
1961:
1722:
1707:
820:
derivatives in the 1940s, mainly in Japan. Allicin became a model for
792:. A Cochrane review found this to be insufficient to draw conclusions.
485:
254:
236:
196:
3355:
3213:
2784:
4076:
4061:
4056:
4006:
4001:
3646:
3565:
3523:
3513:
2750:
2615:
1665:
769:
Allicin has been studied for its potential to treat various kinds of
746:
630:
610:
591:
2292:
1640:
537:
Except where otherwise noted, data are given for materials in their
4011:
3996:
3965:
3955:
3945:
3935:
3916:
3904:
3873:
3868:
3832:
3743:
3596:
3535:
3507:
3497:
3475:
3157:
3142:
3066:
3004:
2989:
2949:
2755:
2730:
2683:
2674:
2601:
2567:
2511:
2506:
2468:
2464:
2438:
2428:
2418:
2408:
2394:
2352:
1692:
1326:
1192:
1101:
1017:
824:
efforts to create other thiamine disulfides. The results included
817:
800:
774:
642:
284:
17:
1938:
132:
125:
4046:
3911:
3877:
3846:
3810:
3668:
3650:
3570:
3527:
3467:
3245:
3146:
3097:
3070:
3062:
3009:
2943:
2759:
2735:
2656:
2605:
2494:
1697:
796:
646:
506:
310:
21:
1306:(2nd ed.). Baltimore: Williams and Wilkins. pp. 1–24.
1071:
3838:
3814:
3772:
3672:
3600:
3439:
3421:
3279:
3240:
3235:
3013:
2999:
2744:
2660:
2555:
2546:
2536:
2515:
2478:
2449:
2444:
2383:
2375:
2361:
2338:
2128:
1607:
1602:
1582:
865:
857:
742:
634:
595:
587:
176:
959:
3842:
3578:
3574:
3531:
3445:
3214:
3081:
3058:
2698:
2575:
2458:
2389:
1655:
1617:
1271:
Yu TH, Wu CM (1989). "Stability of
Allicin in Garlic Juice".
885:
773:
bacterial infections, as well as viral and fungal infections
741:-cysteine. Oxidation of this thioether gives the sulfoxide (
156:
115:
914:
Block E (March 1985). "The
Chemistry of Garlic and Onions".
360:
3777:
3611:
3356:
3302:
3263:
2954:
2917:
2785:
1612:
983:
275:
1443:
1550:
909:
907:
905:
1534:(Fifth ed.). Hoboken: CRC Press. pp. 267–324.
753:(PLP), cleaves alliin, generating allylsulfenic acid (CH
3662:
1243:
812:
It was first isolated and studied in the laboratory by
1104:
Biochimica et
Biophysica Acta (BBA) - General Subjects
902:
590:. When fresh garlic is chopped or crushed, the enzyme
2279:
1394:
400:
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
1300:Garlic: the science and therapeutic application of
410:
InChI=1/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
263:
1523:
1142:Garlic and Other Alliums: The Lore and the Science
1395:Lissiman E, Bhasale AL, Cohen M (November 2014).
73:2-Propene-1-sulfinothioic acid S-2-propenyl ester
4111:
1062:
956:
322:
4165:Transient receptor potential channel modulators
1502:
1092:
1067:
1065:
101:
1195:"Allicin: chemistry and biological properties"
1097:
1095:
1020:"Allicin: chemistry and biological properties"
521:< 25 °C (77 °F; 298 K)
2263:
1566:
64:-(Prop-2-en-1-yl) prop-2-ene-1-sulfinothioate
832:(thiamine tetrahydrofurfuryl disulfide) and
1529:
1401:The Cochrane Database of Systematic Reviews
649:form can also be generated by oxidation of
620:
2277:
2270:
2256:
1573:
1559:
1353:
1298:Hahn G (1996). Koch HP, Lawson LD (eds.).
1246:Journal of Agricultural and Food Chemistry
375:
226:
204:
1479:
1469:
1420:
1371:
1220:
1210:
1167:An introduction to organosulfur chemistry
1144:. Cambridge: Royal Society of Chemistry.
1045:
1035:
342:
1505:Journal of the American Chemical Society
1164:
371:
300:
4112:
2037:
1730:
1135:
1133:
217:
2450:CS gas (2-chlorobenzal malononitrile)
2251:
1554:
1329:Trends in Food Science and Technology
1188:
1186:
1139:
913:
403:Key: JDLKFOPOAOFWQN-UHFFFAOYSA-N
184:
164:
1297:
1270:
4022:N-(p-Amylcinnamoyl)anthranilic acid
3138:N-(p-Amylcinnamoyl)anthranilic acid
2878:N-(p-Amylcinnamoyl)anthranilic acid
1130:
977:
413:Key: JDLKFOPOAOFWQN-UHFFFAOYAO
313:
283:
13:
1496:
1285:10.1111/j.1365-2621.1989.tb07926.x
1183:
1011:
936:10.1038/scientificamerican0385-114
80:-Allyl prop-2-ene-1-sulfinothioate
14:
4176:
1354:Nahas R, Balla A (January 2011).
852:, the active piquant chemical in
2232:
2231:
2217:Garlic Is as Good as Ten Mothers
545:
466:
42:
33:
1437:
1388:
1347:
1320:
1291:
1264:
1237:
728:
641:but occurs naturally only as a
541:(at 25 °C , 100 kPa).
1413:10.1002/14651858.CD006206.pub4
1158:
950:
891:List of phytochemicals in food
475:
472:
460:
1:
4096:Receptor/signaling modulators
2445:CR gas (dibenzoxazepine; DBO)
1116:10.1016/s0304-4165(97)00104-9
896:
1471:10.1371/journal.pone.0248878
1397:"Garlic for the common cold"
7:
3724:Paracetamol (acetaminophen)
2632:Paracetamol (acetaminophen)
2502:Farnesyl thiosalicylic acid
2330:15-Deoxy-Δ-prostaglandin J2
843:
764:
10:
4181:
1580:
1341:10.1016/j.tifs.2016.03.010
1212:10.3390/molecules190812591
1037:10.3390/molecules190812591
807:
15:
4089:
3892:
3365:
3354:
3334:
3311:
3300:
3272:
3223:
3212:
3090:
2926:
2915:
2840:
2794:
2783:
2723:
2302:
2291:
2227:
2208:
2170:
2155:Beurre à la bourguignonne
2104:
2028:
1997:
1937:
1721:
1626:
1590:
1360:Canadian Family Physician
535:
447:
422:
387:
85:
70:
55:
50:
41:
32:
4125:Anti-inflammatory agents
2709:Umbellularia californica
2200:syn-Propanethial-S-oxide
771:multiple drug resistance
621:Structure and occurrence
16:Not to be confused with
3679:N-Arachidonoyl dopamine
3461:Andrographis paniculata
1273:Journal of Food Science
784:, a daily high dose of
4100:Ion channel modulators
3829:Tetrahydrocannabivarin
3324:Tripterygium wilfordii
2690:Tetrahydrocannabiorcol
1656:Common / Bulb
3657:Lysophosphatidic acid
2114:List of garlic dishes
1646:Cipolla di Giarratana
1304:L and related species
1005:10.2298/FUPCT1101009I
625:Allicin features the
584:organosulfur compound
4135:Dietary antioxidants
4037:Pregnenolone sulfate
3858:Euphorbia resinifera
3800:Euphorbia resinifera
3729:Phenylacetylrinvanil
3689:N-Oleoylethanolamide
3637:Homodihydrocapsaicin
3025:Pregnenolone sulfate
2888:Pregnenolone sulfate
2695:Thiopropanal S-oxide
2680:Tetrahydrocannabinol
2368:Allyl isothiocyanate
1947:List of onion dishes
1636:Bangalore rose onion
1532:Handbook of vitamins
850:Allyl isothiocyanate
814:Chester J. Cavallito
57:Preferred IUPAC name
3942:Cannabigerolic acid
3704:Nordihydrocapsaicin
3665:(acidic conditions)
1517:10.1021/ja01239a048
1462:2021PLoSO..1648878J
1258:10.1021/jf60174a007
1165:Cremlyn RJ (1996).
993:Facta Universitatis
928:1985SciAm.252c.114B
916:Scientific American
822:medicinal chemistry
751:pyridoxal phosphate
493: g·mol
146:Beilstein Reference
29:
3905:Vernonia tweediana
3484:African blue basil
3456:Bisandrographolide
3042:Steviol glycosides
2995:Hydroxycitronellal
2741:Dehydroligustilide
2561:Angelica acutiloba
2475:Dehydroligustilide
2220:(1980 documentary)
2190:Diallyl trisulfide
884:chemical found in
568:Infobox references
501:Colourless liquid
27:
4107:
4106:
4085:
4084:
4017:Meclofenamic acid
3823:melegueta peppers
3694:Nonivamide (PAVA)
3430:melegueta peppers
3350:
3349:
3296:
3295:
3208:
3207:
3128:Meclofenamic acid
3051:Stevia rebaudiana
2911:
2910:
2873:Meclofenamic acid
2779:
2778:
2669:melegueta peppers
2642:Phenacyl chloride
2597:N-Methylmaleimide
2587:Methyl salicylate
2532:Hydrogen peroxide
2485:Diallyl disulfide
2347:melegueta peppers
2245:
2244:
2185:Diallyl disulfide
2100:
2099:
1933:
1932:
1541:978-1-4665-1557-4
1313:978-0-683-18147-0
799:are reasons most
749:, which contains
740:
651:diallyl disulfide
600:diallyl disulfide
576:Chemical compound
574:
573:
356:CompTox Dashboard
134:Interactive image
127:Interactive image
4172:
3952:Cannabigerovarin
3684:N-Oleoyldopamine
3590:Euodia ruticarpa
3556:Dihydrocapsaicin
3363:
3362:
3359:
3309:
3308:
3305:
3221:
3220:
3217:
2965:Cooling Agent 10
2924:
2923:
2920:
2792:
2791:
2788:
2310:4-Hydroxynonenal
2300:
2299:
2296:
2281:
2272:
2265:
2258:
2249:
2248:
2235:
2234:
2171:Garlic and onion
2077:…sphaerocephalon
2035:
2034:
1998:Garlic cultivars
1870:…sphaerocephalon
1728:
1727:
1575:
1568:
1561:
1552:
1551:
1546:
1545:
1527:
1521:
1520:
1500:
1494:
1493:
1483:
1473:
1441:
1435:
1434:
1424:
1407:(11): CD006206.
1392:
1386:
1385:
1375:
1351:
1345:
1344:
1324:
1318:
1317:
1295:
1289:
1288:
1268:
1262:
1261:
1241:
1235:
1234:
1224:
1214:
1205:(8): 12591–618.
1190:
1181:
1180:
1162:
1156:
1155:
1140:Block E (2010).
1137:
1128:
1127:
1099:
1090:
1089:
1069:
1060:
1059:
1049:
1039:
1030:(8): 12591–618.
1015:
1009:
1008:
990:
981:
975:
974:
954:
948:
947:
911:
738:
602:. Allicin is an
558:
552:
549:
548:
492:
477:
474:
468:
462:
455:Chemical formula
434:O=S(SC\C=C)C\C=C
380:
379:
364:
362:
346:
326:
315:
304:
287:
267:
238:
230:
219:
208:
188:
168:
136:
129:
105:
46:
37:
30:
26:
4180:
4179:
4175:
4174:
4173:
4171:
4170:
4169:
4160:Allyl compounds
4140:Pungent flavors
4110:
4109:
4108:
4103:
4081:
4072:Tolfenamic acid
3992:Flufenamic acid
3888:
3795:Resiniferatoxin
3788:Ruta graveolens
3551:Diacyl glycerol
3346:
3330:
3292:
3288:
3268:
3254:
3204:
3190:Tolfenamic acid
3183:Ruta graveolens
3123:Flufenamic acid
3086:
3035:Ruta graveolens
2946:(intracellular)
2907:
2903:Tolfenamic acid
2858:Flufenamic acid
2836:
2812:Diacyl glycerol
2775:
2719:
2405:Cannabichromene
2315:4-Oxo-2-nonenal
2287:
2276:
2246:
2241:
2223:
2204:
2195:Allyl mercaptan
2172:
2166:
2157:(garlic butter)
2096:
2024:
1993:
1929:
1717:
1628:Onion cultivars
1622:
1586:
1579:
1549:
1542:
1528:
1524:
1501:
1497:
1456:(3): e0248878.
1442:
1438:
1393:
1389:
1352:
1348:
1325:
1321:
1314:
1296:
1292:
1269:
1265:
1242:
1238:
1191:
1184:
1177:
1163:
1159:
1152:
1138:
1131:
1100:
1093:
1070:
1063:
1016:
1012:
988:
982:
978:
955:
951:
912:
903:
899:
846:
810:
767:
760:
756:
731:
719:
715:
711:
707:
703:
699:
695:
688:
684:
680:
676:
672:
668:
664:
660:
623:
577:
570:
565:
564:
563: ?)
554:
550:
546:
542:
490:
480:
471:
465:
457:
443:
440:
435:
430:
429:
418:
415:
414:
411:
405:
404:
401:
395:
394:
383:
365:
358:
349:
329:
316:
290:
270:
257:
248:
211:
191:
171:
148:
139:
119:
108:
95:
81:
76:
74:
66:
65:
25:
12:
11:
5:
4178:
4168:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4120:Thiosulfinates
4105:
4104:
4090:
4087:
4086:
4083:
4082:
4080:
4079:
4074:
4069:
4064:
4059:
4054:
4049:
4044:
4039:
4034:
4029:
4024:
4019:
4014:
4009:
4004:
3999:
3994:
3989:
3984:
3979:
3974:
3969:
3959:
3949:
3939:
3929:
3924:
3919:
3914:
3909:
3896:
3894:
3890:
3889:
3887:
3886:
3881:
3871:
3866:
3850:
3836:
3826:
3808:
3792:
3780:
3775:
3770:
3765:
3762:Dorrigo pepper
3755:
3741:
3734:Phorbol esters
3731:
3726:
3721:
3711:
3701:
3691:
3686:
3681:
3676:
3666:
3659:
3654:
3644:
3634:
3624:
3619:
3614:
3609:
3604:
3594:
3582:
3568:
3563:
3553:
3548:
3543:
3521:
3511:
3504:Cannabidivarin
3501:
3491:
3472:camphor laurel
3465:
3453:
3448:
3443:
3433:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3369:
3367:
3360:
3352:
3351:
3348:
3347:
3345:
3344:
3338:
3336:
3332:
3331:
3329:
3328:
3315:
3313:
3306:
3298:
3297:
3294:
3293:
3291:
3290:
3286:
3282:
3276:
3274:
3270:
3269:
3267:
3266:
3261:
3256:
3252:
3248:
3243:
3238:
3233:
3227:
3225:
3218:
3210:
3209:
3206:
3205:
3203:
3202:
3197:
3192:
3187:
3175:
3170:
3165:
3160:
3155:
3150:
3140:
3135:
3133:Mefenamic acid
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3094:
3092:
3088:
3087:
3085:
3084:
3079:
3074:
3055:
3039:
3027:
3022:
3017:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2967:
2962:
2957:
2952:
2947:
2941:
2936:
2930:
2928:
2921:
2913:
2912:
2909:
2908:
2906:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2865:
2860:
2855:
2850:
2844:
2842:
2838:
2837:
2835:
2834:
2829:
2826:St John's wort
2819:
2814:
2809:
2806:St John's wort
2798:
2796:
2789:
2781:
2780:
2777:
2776:
2774:
2773:
2768:
2763:
2753:
2748:
2738:
2733:
2727:
2725:
2721:
2720:
2718:
2717:
2712:
2702:
2692:
2687:
2677:
2672:
2654:
2651:Dorrigo pepper
2644:
2639:
2634:
2629:
2619:
2609:
2599:
2594:
2584:
2579:
2572:Sichuan pepper
2565:
2549:
2544:
2542:Isothiocyanate
2539:
2534:
2529:
2524:
2519:
2509:
2504:
2499:
2487:
2482:
2472:
2462:
2452:
2447:
2442:
2435:Cinnamaldehyde
2432:
2422:
2412:
2402:
2397:
2392:
2387:
2365:
2355:
2350:
2332:
2327:
2322:
2317:
2312:
2306:
2304:
2297:
2289:
2288:
2275:
2274:
2267:
2260:
2252:
2243:
2242:
2240:
2239:
2228:
2225:
2224:
2222:
2221:
2212:
2210:
2206:
2205:
2203:
2202:
2197:
2192:
2187:
2182:
2176:
2174:
2168:
2167:
2165:
2164:
2159:
2151:
2149:Garlic chutney
2146:
2141:
2136:
2131:
2126:
2121:
2116:
2110:
2108:
2102:
2101:
2098:
2097:
2095:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2043:
2041:
2032:
2030:Garlic species
2026:
2025:
2023:
2022:
2017:
2012:
2007:
2001:
1999:
1995:
1994:
1992:
1991:
1986:
1981:
1976:
1975:
1974:
1969:
1959:
1954:
1949:
1943:
1941:
1935:
1934:
1931:
1930:
1928:
1927:
1922:
1917:
1912:
1907:
1902:
1897:
1892:
1890:…tribracteatum
1887:
1882:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1822:
1817:
1812:
1807:
1802:
1797:
1792:
1787:
1782:
1777:
1772:
1767:
1762:
1757:
1752:
1747:
1742:
1736:
1734:
1725:
1719:
1718:
1716:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1678:Figueres onion
1675:
1674:
1673:
1668:
1663:
1653:
1648:
1643:
1638:
1632:
1630:
1624:
1623:
1621:
1620:
1615:
1610:
1605:
1600:
1591:
1588:
1587:
1578:
1577:
1570:
1563:
1555:
1548:
1547:
1540:
1522:
1495:
1436:
1387:
1346:
1319:
1312:
1302:Allium sativum
1290:
1263:
1236:
1182:
1175:
1157:
1151:978-0854041909
1150:
1129:
1091:
1061:
1010:
976:
949:
900:
898:
895:
894:
893:
888:
874:-Propanethial-
868:
845:
842:
809:
806:
782:clinical trial
766:
763:
758:
754:
745:). The enzyme
730:
727:
722:
721:
717:
713:
709:
705:
701:
697:
693:
690:
686:
682:
678:
674:
670:
666:
662:
658:
622:
619:
586:obtained from
575:
572:
571:
566:
544:
543:
539:standard state
536:
533:
532:
529:
523:
522:
519:
513:
512:
509:
503:
502:
499:
495:
494:
488:
482:
481:
478:
469:
463:
458:
453:
450:
449:
445:
444:
442:
441:
439:C=CCSS(=O)CC=C
438:
436:
433:
425:
424:
423:
420:
419:
417:
416:
412:
409:
408:
406:
402:
399:
398:
390:
389:
388:
385:
384:
382:
381:
368:
366:
354:
351:
350:
348:
347:
339:
337:
331:
330:
328:
327:
319:
317:
309:
306:
305:
298:
292:
291:
289:
288:
280:
278:
272:
271:
269:
268:
260:
258:
253:
250:
249:
247:
246:
242:
240:
232:
231:
221:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
173:
172:
170:
169:
161:
159:
153:
152:
149:
144:
141:
140:
138:
137:
130:
122:
120:
113:
110:
109:
107:
106:
98:
96:
91:
88:
87:
83:
82:
72:
68:
67:
60:
59:
53:
52:
48:
47:
39:
38:
9:
6:
4:
3:
2:
4177:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4117:
4115:
4102:
4101:
4097:
4094:
4088:
4078:
4075:
4073:
4070:
4068:
4065:
4063:
4060:
4058:
4055:
4053:
4052:Ruthenium red
4050:
4048:
4045:
4043:
4040:
4038:
4035:
4033:
4032:Niflumic acid
4030:
4028:
4025:
4023:
4020:
4018:
4015:
4013:
4010:
4008:
4005:
4003:
4000:
3998:
3995:
3993:
3990:
3988:
3985:
3983:
3980:
3978:
3975:
3973:
3970:
3967:
3963:
3960:
3957:
3953:
3950:
3947:
3943:
3940:
3937:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3913:
3910:
3907:
3906:
3901:
3900:α-Spinasterol
3898:
3897:
3895:
3891:
3885:
3882:
3879:
3875:
3872:
3870:
3867:
3864:
3863:
3859:
3854:
3851:
3848:
3844:
3840:
3837:
3834:
3830:
3827:
3824:
3820:
3816:
3812:
3809:
3806:
3805:
3801:
3796:
3793:
3790:
3789:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3763:
3759:
3756:
3753:
3749:
3745:
3742:
3739:
3735:
3732:
3730:
3727:
3725:
3722:
3719:
3715:
3712:
3709:
3705:
3702:
3699:
3695:
3692:
3690:
3687:
3685:
3682:
3680:
3677:
3674:
3670:
3667:
3664:
3660:
3658:
3655:
3652:
3648:
3645:
3642:
3638:
3635:
3632:
3628:
3627:Homocapsaicin
3625:
3623:
3620:
3618:
3615:
3613:
3610:
3608:
3605:
3602:
3598:
3595:
3592:
3591:
3586:
3583:
3580:
3576:
3572:
3569:
3567:
3564:
3561:
3557:
3554:
3552:
3549:
3547:
3544:
3541:
3540:wild bergamot
3537:
3533:
3529:
3525:
3522:
3519:
3515:
3512:
3509:
3505:
3502:
3499:
3495:
3492:
3489:
3488:camphor basil
3485:
3481:
3477:
3473:
3469:
3466:
3463:
3462:
3457:
3454:
3452:
3449:
3447:
3444:
3441:
3437:
3434:
3431:
3427:
3423:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3370:
3368:
3364:
3361:
3358:
3353:
3343:
3342:Ruthenium red
3340:
3339:
3337:
3333:
3326:
3325:
3320:
3317:
3316:
3314:
3310:
3307:
3304:
3299:
3289:
3283:
3281:
3278:
3277:
3275:
3271:
3265:
3262:
3260:
3257:
3255:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3228:
3226:
3222:
3219:
3216:
3211:
3201:
3198:
3196:
3193:
3191:
3188:
3185:
3184:
3179:
3176:
3174:
3173:Ruthenium red
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3153:Niflumic acid
3151:
3148:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3095:
3093:
3089:
3083:
3080:
3078:
3075:
3073:; indirectly)
3072:
3068:
3064:
3060:
3056:
3053:
3052:
3047:
3043:
3040:
3037:
3036:
3031:
3028:
3026:
3023:
3021:
3018:
3015:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2980:Frescolat MGA
2978:
2975:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2945:
2942:
2940:
2937:
2935:
2932:
2931:
2929:
2925:
2922:
2919:
2914:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2883:Niflumic acid
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2845:
2843:
2839:
2833:
2830:
2827:
2823:
2820:
2818:
2815:
2813:
2810:
2807:
2803:
2800:
2799:
2797:
2793:
2790:
2787:
2782:
2772:
2771:Ruthenium red
2769:
2767:
2764:
2761:
2757:
2754:
2752:
2749:
2746:
2742:
2739:
2737:
2734:
2732:
2729:
2728:
2726:
2722:
2716:
2713:
2710:
2706:
2703:
2700:
2696:
2693:
2691:
2688:
2685:
2681:
2678:
2676:
2673:
2670:
2666:
2662:
2658:
2655:
2652:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2627:
2623:
2620:
2617:
2613:
2610:
2607:
2603:
2600:
2598:
2595:
2592:
2588:
2585:
2583:
2582:Methylglyoxal
2580:
2577:
2573:
2569:
2566:
2563:
2562:
2557:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2517:
2513:
2510:
2508:
2505:
2503:
2500:
2497:
2496:
2491:
2488:
2486:
2483:
2480:
2476:
2473:
2470:
2466:
2463:
2460:
2456:
2455:Cuminaldehyde
2453:
2451:
2448:
2446:
2443:
2440:
2436:
2433:
2430:
2426:
2423:
2420:
2416:
2413:
2410:
2406:
2403:
2401:
2398:
2396:
2393:
2391:
2388:
2385:
2381:
2377:
2373:
2369:
2366:
2363:
2359:
2356:
2354:
2351:
2348:
2344:
2340:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2316:
2313:
2311:
2308:
2307:
2305:
2301:
2298:
2295:
2290:
2286:
2283:
2273:
2268:
2266:
2261:
2259:
2254:
2253:
2250:
2238:
2230:
2229:
2226:
2219:
2218:
2214:
2213:
2211:
2207:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2177:
2175:
2169:
2163:
2160:
2158:
2156:
2152:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2111:
2109:
2107:
2103:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2062:…neapolitanum
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2044:
2042:
2040:
2036:
2033:
2031:
2027:
2021:
2018:
2016:
2015:Snow Mountain
2013:
2011:
2010:Garlic chives
2008:
2006:
2003:
2002:
2000:
1996:
1990:
1987:
1985:
1982:
1980:
1977:
1973:
1972:Zwiebelkuchen
1970:
1968:
1965:
1964:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1944:
1942:
1940:
1936:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1865:…siskiyouense
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1818:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1796:
1795:…campanulatum
1793:
1791:
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1781:
1778:
1776:
1773:
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1768:
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1761:
1758:
1756:
1755:…ampeloprasum
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1737:
1735:
1733:
1729:
1726:
1724:
1723:Onion species
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1200:
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1178:
1176:0-471-95512-4
1172:
1168:
1161:
1153:
1147:
1143:
1136:
1134:
1125:
1121:
1117:
1113:
1110:(2): 233–44.
1109:
1105:
1098:
1096:
1087:
1083:
1079:
1075:
1074:Die Pharmazie
1068:
1066:
1057:
1053:
1048:
1043:
1038:
1033:
1029:
1025:
1021:
1014:
1006:
1002:
998:
994:
987:
980:
972:
968:
965:(2): 249–52.
964:
960:
953:
945:
941:
937:
933:
929:
925:
921:
917:
910:
908:
906:
901:
892:
889:
887:
883:
879:
877:
873:
869:
867:
863:
859:
855:
851:
848:
847:
841:
839:
835:
834:benfothiamine
831:
830:fursultiamine
827:
823:
819:
815:
805:
802:
798:
793:
791:
787:
783:
778:
776:
772:
762:
752:
748:
744:
736:
726:
691:
656:
655:
654:
652:
648:
644:
640:
637:. Allicin is
636:
632:
628:
627:thiosulfinate
618:
616:
615:sulfenic acid
612:
607:
605:
601:
597:
593:
589:
585:
581:
569:
562:
557:
540:
534:
530:
528:
527:Boiling point
525:
524:
520:
518:
517:Melting point
515:
514:
510:
508:
505:
504:
500:
497:
496:
489:
487:
484:
483:
459:
456:
452:
451:
446:
437:
432:
431:
428:
421:
407:
397:
396:
393:
386:
378:
374:
373:DTXSID6043707
370:
369:
367:
357:
353:
352:
345:
341:
340:
338:
336:
333:
332:
325:
321:
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318:
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308:
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297:
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279:
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273:
266:
262:
261:
259:
256:
252:
251:
244:
243:
241:
239:
234:
233:
229:
225:
222:
220:
218:ECHA InfoCard
215:
214:
207:
203:
202:
200:
198:
195:
194:
187:
183:
182:
180:
178:
175:
174:
167:
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158:
155:
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143:
142:
135:
131:
128:
124:
123:
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117:
112:
111:
104:
100:
99:
97:
94:
90:
89:
84:
79:
69:
63:
58:
54:
49:
45:
40:
36:
31:
23:
19:
4092:
4091:
3932:Cannabigerol
3903:
3856:
3798:
3786:
3748:black pepper
3708:chili pepper
3641:chili pepper
3631:chili pepper
3622:Hepoxilin B3
3617:Hepoxilin A3
3588:
3560:chili pepper
3518:chili pepper
3459:
3435:
3322:
3181:
3108:Clotrimazole
3049:
3033:
2985:Frescolat ML
2893:Progesterone
2802:Adhyperforin
2715:WIN 55,212-2
2708:
2559:
2527:Hepoxilin B3
2522:Hepoxilin A3
2493:
2425:Cannabigerol
2357:
2215:
2179:
2173:constituents
2154:
2144:Garlic bread
2139:Garlic press
2119:Black garlic
2038:
1925:…yosemitense
1920:…victorialis
1905:…tuolumnense
1810:…cratericola
1750:…aflatunense
1731:
1595:
1581:
1531:
1525:
1511:(11): 1950.
1508:
1504:
1498:
1453:
1449:
1439:
1404:
1400:
1390:
1363:
1359:
1349:
1332:
1328:
1322:
1303:
1299:
1293:
1276:
1272:
1266:
1252:(2): 273–5.
1249:
1245:
1239:
1202:
1198:
1166:
1160:
1141:
1107:
1103:
1077:
1073:
1027:
1023:
1013:
996:
992:
979:
962:
958:
952:
922:(3): 114–9.
919:
915:
882:lachrymatory
875:
871:
826:sulbutiamine
811:
794:
779:
768:
734:
732:
729:Biosynthesis
723:
624:
608:
579:
578:
186:ChEMBL359965
86:Identifiers
77:
75:3-prop-1-ene
71:Other names
61:
4155:Antifungals
4130:Antibiotics
4067:Tivanisiran
3972:Capsazepine
3884:Zucapsaicin
3752:long pepper
3718:Pacific yew
3607:GSK1016790A
3494:Cannabidiol
3480:camphorweed
3168:RQ-00203078
3163:PF-05105679
3103:Capsazepine
2868:GSK2293017A
2832:Substance P
2817:GSK1702934A
2766:PF-04745637
2705:Umbellulone
2626:Pacific yew
2612:Oleocanthal
2591:wintergreen
2552:Ligustilide
2415:Cannabidiol
2380:horseradish
2162:Garlic soup
2106:Garlic food
2082:…triquetrum
2052:…drummondii
1989:Sogan-dolma
1967:Flammkuchen
1900:…triquetrum
1880:…stipitatum
1840:…platycaule
1825:…fistulosum
1820:…cristophii
1775:…bisceptrum
1770:…atrorubens
1760:…amplectens
1745:…acuminatum
1366:(1): 31–6.
1080:(1): 10–4.
999:(1): 9–20.
862:horseradish
838:glutathione
790:common cold
780:In a small
685:SOH + 2 RCO
604:antifeedant
531:decomposes
511:1.112 g cm
498:Appearance
448:Properties
224:100.007.935
166:CHEBI:28411
4114:Categories
3962:Cannabinol
3862:pooissonii
3853:Tinyatoxin
3804:pooissonii
3768:Probenecid
3758:Polygodial
3714:Paclitaxel
3698:PAVA spray
3585:Evodiamine
3536:pepperwort
3451:Anandamide
3418:α-Sanshool
3366:Activators
3319:Triptolide
3312:Activators
3224:Activators
3200:TRPM4-IN-5
3118:Elismetrep
3046:stevioside
2974:eucalyptus
2970:Eucalyptol
2934:ADP-ribose
2927:Activators
2863:GSK417651A
2822:Hyperforin
2795:Activators
2675:Tear gases
2647:Polygodial
2637:PF-4840154
2622:Paclitaxel
2490:Dicentrine
2400:Bradykinin
2335:α-Sanshool
2303:Activators
2285:modulators
2134:Garlic oil
2124:Persillade
2047:…canadense
1979:Onion ring
1962:Onion cake
1939:Onion food
1910:…unifolium
1895:…tricoccum
1875:…stellatum
1860:…shevockii
1855:…sanbornii
1835:…monanthum
1790:…caeruleum
1780:…bolanderi
1279:(4): 977.
897:References
700:SOH → CH
486:Molar mass
344:3C39BY17Y6
255:IUPHAR/BPS
197:ChemSpider
114:3D model (
93:CAS Number
4093:See also:
4077:TRPV3-74a
4062:SB-705498
4057:SB-366791
4007:Lanthanum
4002:HC-067047
3922:Asivatrep
3783:Rutamarin
3647:Incensole
3597:Gingerols
3566:Estradiol
3542:, others)
3524:Carvacrol
3514:Capsaicin
3408:13-oxoODE
3398:12S-HpETE
3378:5',6'-EET
3178:Rutamarin
3077:Thio-BCTC
3030:Rutamarin
2960:Coolact P
2751:HC-030031
2616:olive oil
2512:Gingerols
2325:12S-HpETE
1830:…koreanum
1805:…chinense
1785:…burlewii
1740:…abramsii
1335:: 49–56.
1199:Molecules
1169:. Wiley.
1024:Molecules
786:extracted
747:alliinase
631:alliinase
611:thioester
594:converts
592:alliinase
245:208-727-7
237:EC Number
4027:NGD-8243
4012:Mavatrep
3997:GRC-6211
3966:cannabis
3956:cannabis
3946:cannabis
3936:cannabis
3917:AMG-9810
3893:Blockers
3874:Vanillin
3869:Tramadol
3833:cannabis
3811:Shogaols
3744:Piperine
3508:cannabis
3498:cannabis
3476:rosemary
3393:12S-HETE
3388:9-oxoODE
3335:Blockers
3285:PI(4,5)P
3273:Blockers
3251:PI(3,5)P
3158:Ononetin
3143:Nicotine
3091:Blockers
3067:fructose
3059:tastants
3005:Linalool
2990:Geraniol
2950:CIM-0216
2841:Blockers
2756:Nicotine
2731:A-967079
2724:Blockers
2684:cannabis
2657:Shogaols
2602:Nicotine
2568:Linalool
2507:Formalin
2469:turmeric
2465:Curcumin
2439:cinnamon
2429:cannabis
2419:cannabis
2409:cannabis
2395:ASP-7663
2353:Acrolein
2237:Category
2092:…vineale
2087:…ursinum
2005:Elephant
1952:Blooming
1915:…validum
1885:…textile
1850:…punctum
1845:…praecox
1815:…crispum
1800:…cernuum
1693:Scallion
1651:Cocktail
1490:33740023
1450:PLOS ONE
1431:25386977
1382:21322286
1231:25153873
1086:14964414
1056:25153873
858:radishes
844:See also
818:thiamine
801:bacteria
797:proteins
775:in vitro
765:Research
677:O → 2 CH
643:racemate
151:1752823
103:539-86-6
28:Allicin
18:Allysine
4047:RN-9893
4042:RN-1734
3912:AMG-517
3878:vanilla
3847:oregano
3819:Sichuan
3797:(RTX) (
3773:Protons
3736:(e.g.,
3669:Menthol
3651:incense
3571:Eugenol
3528:oregano
3468:Camphor
3436:Allicin
3426:Sichuan
3413:20-HETE
3403:13-HODE
3246:ML2-SA1
3147:tobacco
3098:AMG-333
3071:sucrose
3063:glucose
3061:(e.g.,
3044:(e.g.,
3010:Menthol
2944:Calcium
2760:tobacco
2736:AM-0902
2665:Sichuan
2606:tobacco
2495:Lindera
2372:mustard
2358:Allicin
2343:Sichuan
2320:4,5-EET
2282:channel
2209:Related
2180:Allicin
2072:…roseum
2067:…nigrum
2039:Allium…
1984:Pickled
1765:…anceps
1732:Allium…
1713:Vidalia
1698:Shallot
1598:species
1481:7978267
1458:Bibcode
1422:6465033
1373:3024156
1222:6271412
1124:9528659
1047:6271412
971:1667340
944:3975593
924:Bibcode
854:mustard
808:History
737:-allyl-
708:S(O)SCH
673:H + H
669:+ 2 RCO
647:racemic
580:Allicin
561:what is
559: (
507:Density
311:PubChem
302:Allicin
22:halicin
4150:Garlic
4145:Allium
3987:DHEA-S
3839:Thymol
3815:ginger
3738:4α-PDD
3601:ginger
3440:garlic
3422:ginger
3383:9-HODE
3280:ML-SI3
3241:ML-SA1
3236:MK6-83
3057:Sweet
3020:PMD 38
3000:Icilin
2853:DHEA-S
2745:celery
2661:ginger
2556:celery
2547:JT-010
2537:Icilin
2516:ginger
2479:celery
2384:wasabi
2376:radish
2362:garlic
2339:ginger
2129:Pistou
1688:Potato
1661:Yellow
1641:Calçot
1608:Garlic
1603:Chives
1596:Allium
1583:Allium
1538:
1488:
1478:
1429:
1419:
1380:
1370:
1310:
1229:
1219:
1173:
1148:
1122:
1084:
1054:
1044:
969:
942:
886:onions
880:, the
878:-oxide
866:wasabi
743:alliin
645:. The
639:chiral
635:alliin
596:alliin
588:garlic
582:is an
556:verify
553:
491:162.26
427:SMILES
285:C07600
177:ChEMBL
51:Names
3977:DCDPC
3843:thyme
3579:clove
3575:basil
3532:thyme
3446:AM404
3373:2-APB
3259:SF-22
3231:EVP21
3215:TRPML
3113:DCDPC
3082:WS-12
2848:DCDPC
2699:onion
2576:thyme
2498:spp.)
2459:cumin
2390:AM404
2057:…moly
1957:Fried
1703:Sweet
1683:Pearl
1671:White
1618:Onion
989:(PDF)
757:=CHCH
712:CH=CH
704:=CHCH
696:=CHCH
681:=CHCH
661:CH=CH
392:InChI
324:65036
206:58548
157:ChEBI
116:JSmol
3982:DHEA
3927:BCTC
3821:and
3778:RhTx
3673:mint
3661:Low
3612:Heat
3546:DHEA
3428:and
3357:TRPV
3303:TRPP
3264:SN-2
3195:TPPO
3014:mint
2955:Cold
2939:BCTC
2918:TRPM
2898:Pyr3
2786:TRPC
2667:and
2345:and
2294:TRPA
2020:Solo
1708:Tree
1613:Leek
1536:ISBN
1486:PMID
1427:PMID
1405:2020
1378:PMID
1308:ISBN
1227:PMID
1171:ISBN
1146:ISBN
1120:PMID
1108:1379
1082:PMID
1052:PMID
967:PMID
940:PMID
864:and
692:2 CH
657:(SCH
335:UNII
296:MeSH
276:KEGG
265:2419
3048:) (
2280:TRP
1666:Red
1513:doi
1476:PMC
1466:doi
1417:PMC
1409:doi
1368:PMC
1337:doi
1281:doi
1254:doi
1217:PMC
1207:doi
1112:doi
1042:PMC
1032:doi
1001:doi
932:doi
920:252
872:syn
716:+ H
633:on
613:of
361:EPA
314:CID
20:or
4116::
4098:•
3845:,
3817:,
3750:,
3663:pH
3577:,
3538:,
3534:,
3530:,
3486:,
3482:,
3478:,
3474:,
3424:,
3069:,
3065:,
2663:,
2574:,
2558:,
2382:,
2378:,
2374:,
2341:,
1509:66
1507:.
1484:.
1474:.
1464:.
1454:16
1452:.
1448:.
1425:.
1415:.
1403:.
1399:.
1376:.
1364:57
1362:.
1358:.
1333:52
1331:.
1277:54
1275:.
1250:19
1248:.
1225:.
1215:.
1203:19
1201:.
1197:.
1185:^
1132:^
1118:.
1106:.
1094:^
1078:59
1076:.
1064:^
1050:.
1040:.
1028:19
1026:.
1022:.
995:.
991:.
963:74
961:.
938:.
930:.
918:.
904:^
860:,
856:,
840:.
828:,
653::
470:10
3968:)
3964:(
3958:)
3954:(
3948:)
3944:(
3938:)
3934:(
3908:)
3902:(
3880:)
3876:(
3865:)
3860:/
3855:(
3849:)
3841:(
3835:)
3831:(
3825:)
3813:(
3807:)
3802:/
3791:)
3785:(
3764:)
3760:(
3754:)
3746:(
3740:)
3720:)
3716:(
3710:)
3706:(
3700:)
3696:(
3675:)
3671:(
3653:)
3649:(
3643:)
3639:(
3633:)
3629:(
3603:)
3599:(
3593:)
3587:(
3581:)
3573:(
3562:)
3558:(
3526:(
3520:)
3516:(
3510:)
3506:(
3500:)
3496:(
3490:)
3470:(
3464:)
3458:(
3442:)
3438:(
3432:)
3420:(
3327:)
3321:(
3287:2
3253:2
3186:)
3180:(
3149:)
3145:(
3054:)
3038:)
3032:(
3016:)
3012:(
2976:)
2972:(
2828:)
2824:(
2808:)
2804:(
2762:)
2758:(
2747:)
2743:(
2711:)
2707:(
2701:)
2697:(
2686:)
2682:(
2671:)
2659:(
2653:)
2649:(
2628:)
2624:(
2618:)
2614:(
2608:)
2604:(
2593:)
2589:(
2578:)
2570:(
2564:)
2554:(
2518:)
2514:(
2492:(
2481:)
2477:(
2471:)
2467:(
2461:)
2457:(
2441:)
2437:(
2431:)
2427:(
2421:)
2417:(
2411:)
2407:(
2386:)
2370:(
2364:)
2360:(
2349:)
2337:(
2271:e
2264:t
2257:v
1574:e
1567:t
1560:v
1544:.
1519:.
1515::
1492:.
1468::
1460::
1433:.
1411::
1384:.
1343:.
1339::
1316:.
1287:.
1283::
1260:.
1256::
1233:.
1209::
1179:.
1154:.
1126:.
1114::
1088:.
1058:.
1034::
1007:.
1003::
997:9
973:.
946:.
934::
926::
876:S
759:2
755:2
739:L
735:S
720:O
718:2
714:2
710:2
706:2
702:2
698:2
694:2
689:H
687:2
683:2
679:2
675:2
671:3
667:2
665:)
663:2
659:2
551:N
479:2
476:S
473:O
467:H
464:6
461:C
363:)
359:(
118:)
78:S
62:S
24:.
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