1228:
334:
198:
800:
577:
894:
572:
28:
37:
767:
1457:
Phloroglucinol is used in plant culture media. It demonstrates both cytokinin-like and auxin-like activity. Phloroglucinol increases shoot formation and somatic embryogenesis in several horticultural and grain crops. When added to rooting media together with auxin, phloroglucinol further stimulates
2057:
Blanchard, C, Pouchain, D, Vanderkam, P, Perault-Pochat, M, Boussageon, R, Vaillant-Roussel, H (2018). "Efficacy of phloroglucinol for treatment of abdominal pain: a systematic review of literature and meta-analysis of randomised controlled trials versus placebo".
1354:
and other related gastrointestinal disorders A 2018 review found insufficient evidence that phloroglucinol was effective for treating abdominal pain A 2020 review found insufficient evidence that phloroglucinol was effective for treating pain caused by
999:
From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116–117 °C, but the anhydrous form melts at a much higher temperature, at 218–220 °C. It does not boil intact, but it does sublime.
2101:
Clara B, Paul V, Denis P, Stéphanie M, Hélène VR, Rémy B (2020). "Efficacy of phloroglucinol for the treatment of pain of gynaecologic or obstetrical origin: a systematic review of literature of randomised controlled trials".
2147:"Phloroglucinol-Derived Medications are Effective in Reducing Pain and Spasms of Urinary and Biliary Tracts: Results of Phase 3 Multicentre, Open-Label, Randomized, Comparative Studies of Clinical Effectiveness and Safety"
585:
1820:
Na, M.; Jang, J.; Min, B. S.; Lee, S. J.; Lee, M. S.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. (2006). "Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from
Dryopteris crassirhizoma".
2392:
1890:
Okada, Y.; Ishimaru, A.; Suzuki, R.; Okuyama, T. (2004). "A New
Phloroglucinol Derivative from the Brown AlgaEisenia bicyclis: Potential for the Effective Treatment of Diabetic Complications".
552:
1008:
3200:
3195:
2385:
1254:
1232:
3191:
679:
3219:
3205:
3181:
3176:
3172:
3167:
3214:
3210:
3162:
2378:
1428:
3340:
3296:
3157:
3152:
3148:
3144:
1168:
side-chains. Two side-chains are prenyl groups and one is an isovaleryl group. Humulone is a bitter-tasting chemical compound found in the resin of mature hops (
2249:
3321:
3139:
3135:
3131:
527:
3186:
3126:
3122:
3118:
1018:
1952:
Shibata, T.; Kawaguchi, S.; Hama, Y.; Inagaki, M.; Yamaguchi, K.; Nakamura, T. (2004). "Local and chemical distribution of phlorotannins in brown algae".
1454:
formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as phloroglucinol, during pine tannins extraction.
3088:
3083:
3075:
3071:
1855:
Eschler, B. M.; Pass, D. M.; Willis, R.; Foley, W. J. (2000). "Distribution of foliar formylated phloroglucinol derivatives amongst
Eucalyptus species".
1603:
Fiege, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J.; Garbe, D.; Paulus, W. (2000). "Phenol
Derivatives".
3113:
3093:
3066:
3041:
780:
3261:
1028:
3245:
3061:
2248:
A facile two-step
Synthesis of 1,3,5-trinitrobenzene. Bottaro Jeffrey C, Malhotra Ripudaman and Dodge Allen, Synthesis, 2004, no 4, pages 499-500,
884:
A modern synthesis of phloroglucinol involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from
3306:
3301:
1781:
1547:(The most striking property of this substance is that it tastes extremely sweet, for which reason it may be named "phloroglucin" until further .)
1139:
3240:
3036:
1545:"Die auffallendste Eigenschaft dieses Körpers ist, daſs er überaus süſs schmeckt, weſshalb er bis auf weiteres Phloroglucin genannt sein mag."
1925:
Blackman, A. J.; Rogers, G. I.; Volkman, J. K. (1988). "Phloroglucinol
Derivatives from Three Australian Marine Algae of the Genus Zonaria".
1135:
2942:
383:
2267:
Sealy-Fisher, V. J.; Pizzi, A. (1992). "Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization".
1363:
conditions. A 2022 phase 3 study conducted in Italy on 364 patients indicated phloroglucinol and its derivative must be as effective as
1131:
991:
For the neutral compound, the keto tautomers are undetectable spectroscopically. Upon deprotonation, the keto tautomer predominates.
1638:
Martin Lohrie; Wilhelm Knoche (1993). "Dissociation and Keto-Enol
Tautomerism of Phloroglucinol and its Anions in Aqueous Solution".
2145:
Corvino, Angela; Magli, Elisa; Minale, Massimiliano; Autelitano, Andrea; Valente, Valeria; Pierantoni, Giovanna Maria (2023-02-01).
2357:
675:
2025:
2980:
2417:
2402:
2255:
775:
2725:
1364:
988:
But it behaves also like a benzenetriol as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.
1622:
2302:
Teixeira da Silva, Jaime A.; Dobránszki, Judit; Ross, Silvia (2013-02-01). "Phloroglucinol in plant tissue culture".
348:
2353:
Lignin production and detection in wood. John M. Harkin, U.S. Forest
Service Research Note FPL-0148, November 1966 (
2344:
Oshitna, K., and
Tollens, B., Ueber Spectral-reactionen des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)
787:
1393:
subgroup of the
Anatomical Therapeutic Chemical Classification System. It also has the D02.755.684 code in the
1313:
1212:
1803:
1261:
1198:, produce phloroglucinol and phloroglucinol derivatives. Brown algae also produce a type of tannins known as
2785:
1246:
633:
291:
193:
115:
2613:
1522:
1273:
1265:
312:
155:
2370:
1400:
section of the Medical Subject Headings (MeSH) codes by the United States National Library of Medicine.
1038:
Phloroglucinol readily forms 5-aminoresorcinol (aka Phloramine) in aqueous ammonia at low temperatures.
663:
576:
2973:
2915:
2677:
643:
571:
490:
2202:
2845:
1295:
699:
205:
659:
3359:
1394:
1304:
1286:
1110:
715:
329:
2958:
2519:
1278:
1269:
1241:
1207:
509:
1096:
that occur naturally in certain plant species. It is also produced by brown algae and bacteria.
2529:
1216:
1756:
1561:
3292:
2966:
2835:
2806:
2430:
1728:
1432:
1290:
885:
599:
564:
861:
official nomenclature rules of chemical compounds. Many such monophenolics are often termed
703:
2559:
1182:
1157:
1116:
1093:
853:(1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "
695:
300:
55:
687:
8:
3364:
2881:
2852:
2497:
1965:
1371:
1327:
1066:
1024:
683:
175:
91:
81:
2354:
1346:
In some countries and in veterinary medicine, phloroglucinol is used as a treatment for
333:
197:
135:
69:
phloroglucine, 1,3,5-benzenetriol , 1,3,5-trihydroxybenzene or cyclohexane-1,3,5-trione
2760:
2594:
2327:
2284:
2179:
2127:
2083:
2032:
1990:
Achkar, J.; Xian, M.; Zhao, H.; Frost, J. W. (2005). "Biosynthesis of Phloroglucinol".
1969:
1497:
1293:
and NADP to produce phloroglucinol, NADPH, and H. It is found in the bacterium species
878:
1868:
3079:
2857:
2799:
2579:
2554:
2319:
2184:
2166:
2131:
2119:
2075:
2007:
1907:
1872:
1837:
1797:
1618:
1490:
1481:
A solution of hydrochloric acid and phloroglucinol is also used for the detection of
1104:
830:
799:
2331:
1973:
1227:
3326:
3109:
2840:
2715:
2654:
2589:
2472:
2311:
2288:
2276:
2174:
2158:
2111:
2087:
2067:
1999:
1961:
1934:
1899:
1864:
1829:
1709:
1674:
1647:
1610:
1582:
1534:
1467:
1443:
1439:
1188:
1121:
814:
538:
458:
406:
3311:
2750:
2361:
1604:
1486:
1170:
1004:
625:
2227:
1478:
with phloroglucinol to produce a colored compound with high molar absorptivity.
264:
2907:
2862:
2162:
2115:
1833:
1194:
1042:
854:
834:
758:
647:
2315:
2071:
1691:
893:
744:
3353:
3316:
2745:
2645:
2599:
2584:
2549:
2524:
2452:
2323:
2170:
2146:
1678:
1614:
1586:
1538:
1360:
1351:
1321:
1302:
The legume-root nodulating, microsymbiotic nitrogen-fixing bacterium species
1014:
846:
655:
475:
447:
186:
1504:, for the qualitative detection of free hydrochloric acid in gastric juice.
667:
3057:
3031:
2990:
2720:
2539:
2477:
2462:
2406:
2188:
2123:
2079:
2011:
1911:
1876:
1841:
1713:
1665:
Gulati, K. C.; Seth, S. R.; Venkataraman, K. (1935). "Phloroacetophenone".
1387:
1199:
1153:
1086:
842:
533:
27:
3287:
2925:
2902:
2823:
2780:
2775:
2740:
2669:
2623:
2569:
2564:
2544:
2534:
2487:
2400:
1485:(Wiesner test). A brilliant red color develops, owing to the presence of
1451:
1447:
1416:
1250:
691:
1938:
1761:(1st ed.). New York: D Appleton and Company. pp. 193 & 253
1651:
1408:
Phloroglucinol is mainly used as a coupling agent in printing. It links
671:
2937:
2897:
2892:
2887:
2872:
2770:
2735:
2730:
2710:
2633:
2628:
2482:
2467:
2457:
2280:
1335:
1317:
1316:, further decarboxylated to phloroglucinol, which is dehydroxylated to
1177:
1165:
1149:
1144:
1127:
1070:
913:
862:
850:
469:
429:
206:
166:
2003:
1903:
711:
3235:
2947:
2930:
2765:
2687:
2664:
2509:
2447:
1420:
1409:
1356:
1347:
1331:
1272:(pyrogallol) to produce 1,3,5-trihydroxybenzene (phloroglucinol) and
1078:
1062:
1061:
ring A substitution pattern. Indeed, it was originally prepared from
1058:
1046:
1032:
944:. Evidence for this equilibrium is provided by the formation of the
905:
874:
838:
639:
1253:. Then decarboxylation followed by the cyclization of the activated
757:
Except where otherwise noted, data are given for materials in their
36:
3026:
2988:
2818:
2705:
2514:
1501:
1475:
1367:
for the treatment of pain and spasms of biliary or urinary tracts.
1309:
1161:
1082:
941:
483:
239:
232:
723:
621:
114:
3277:
3021:
2574:
1471:
901:
651:
609:
479:
251:
2301:
1692:
Maier, G.; Reisenauer, H. P.; Schäfer, U.; Balli, H. (1988). "C
1482:
1102:
derivatives are present in the fronds of the coastal woodfern,
1074:
146:
1572:
1415:
It is useful for the industrial synthesis of pharmaceuticals (
940:, phloroglucinol in principle exists in equilibrium with keto
617:
3282:
945:
909:
858:
707:
275:
126:
104:
2144:
1069:. Additionally, the compound can be similarly prepared from
317:
1951:
1700:(1,2,3,4-Pentatetraene-1,5-dione), a New Oxide of Carbon".
1637:
1560:(London, England: Longmans, Green, and Co., 1913), vol. 4,
1489:
groups in the lignin. A similar test can be performed with
1424:
1099:
937:
613:
223:
1889:
1017:
can be synthesized from phloroglucinol by a reaction with
929:
Phloroglucinol is a weak triprotic acid. The first two pK
1602:
1573:
H. T. Clarke and W. W. Hartman (1929). "Phloroglucinol".
2203:"Intermediate Pharmaceutical Ingredients - Flopropione"
2100:
1438:
Phloroglucinolysis is an analytical technique to study
1854:
1664:
1249:. The synthesis begins with the condensation of three
2304:
In Vitro Cellular & Developmental Biology - Plant
2230:. The United States Patent and Trademark Office. 1984
1924:
1245:, biosynthesis of phloroglucinol is performed with a
924:
605:
2056:
1989:
1257:product leads to the formation of phloroglucinol.
908:. Because the triaminobenzene also exists as its
2266:
1754:
3351:
1779:
873:In 1855, phloroglucinol was first prepared from
263:
1391:Drugs for functional gastrointestinal disorders
90:
1606:Ullmann's Encyclopedia of Industrial Chemistry
1500:, an alcoholic solution of phloroglucinol and
1446:. The reaction makes use of phloroglucinol as
1065:, a compound isolated from fruit trees, using
1057:Phloroglucinol is also generally found in the
829:. It is a colorless solid. It is used in the
719:
357:InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
2974:
2386:
1733:(1st ed.). London: The Cavendish Society
1021:in the presence of a zinc chloride catalyst.
900:The synthesis is noteworthy because ordinary
367:InChI=1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
2094:
2050:
1822:Bioorganic & Medicinal Chemistry Letters
1819:
1727:Gmelin, Leopold (1862). Watts, Henry (ed.).
1370:Phloroglucinols acylated derivatives have a
1792:. Archived from the original on 2011-07-11.
1114:. The anthelmintic activity of the root of
1035:of 1,3,5-cyclohexanetrione (phloroglucin).
868:
2981:
2967:
2393:
2379:
1750:
1748:
1543:On p. 120, Hlasiwetz named phloroglucin:
1384:Other drugs for functional bowel disorders
1164:is a phloroglucinol derivative with three
841:. Phloroglucinol is one of three isomeric
332:
196:
174:
2178:
1985:
1983:
1758:A Treatise on Chemistry, Volume 3, Part 3
1598:
1596:
1520:
299:
1992:Journal of the American Chemical Society
1427:(2,4,6-triamino-1,3,5-trinitrobenzene),
1226:
798:
1745:
1702:Angewandte Chemie International Edition
1276:. It is found in the bacterium species
328:
3352:
1980:
1780:C. Michael Hogan (December 14, 2008).
1755:Roscoe, H.E.; Schorlemmer, C. (1893).
1726:
1593:
1474:. This test relies on reaction of the
1052:
452:219 °C (426 °F; 492 K)
187:
2962:
2403:functional gastrointestinal disorders
2374:
2228:"Synthesis of trinitrophloroglucinol"
1815:
1813:
1382:It has the A03AX12 code in the A03AX
1377:
360:Key: QCDYQQDYXPDABM-UHFFFAOYSA-N
154:
134:
1685:
1365:nonsteroidal anti-inflammatory drugs
537:
2726:Dimethylaminopropionylphenothiazine
1857:Biochemical Systematics and Ecology
1466:Phloroglucinol is a reagent of the
370:Key: QCDYQQDYXPDABM-UHFFFAOYAF
254:
238:
231:
13:
1966:10.1023/B:JAPH.0000047781.24993.0a
1810:
1009:1-(2,4,6-Trihydroxyphenyl)ethanone
994:
925:Tautomerism and acid-base behavior
904:derivatives are unreactive toward
35:
26:
14:
3376:
1730:Hand-Book of Chemistry, Volume 15
1558:A Dictionary of Applied Chemistry
1341:
1156:are two phloroglucinols found in
1527:Annalen der Chemie und Pharmacie
892:
765:
575:
570:
2347:
2338:
2295:
2260:
2242:
2220:
2195:
2138:
2026:"Phloroglucinol Summary Report"
2018:
1945:
1918:
1883:
1848:
1773:
1461:
1403:
1222:
1124:, a phloroglucinol derivative.
1041:Reaction of phloroglucinol and
1031:and others, can be obtained by
912:tautomer, it is susceptible to
761:(at 25 °C , 100 kPa).
2882:Primarily dopamine antagonists
2831:Quaternary ammonium compounds:
1720:
1658:
1631:
1566:
1550:
1514:
1314:phloroglucinol carboxylic acid
1213:phloroglucinol carboxylic acid
1120:has been claimed to be due to
1:
1869:10.1016/S0305-1978(99)00123-4
1507:
1262:pyrogallol hydroxytransferase
2786:Trimethyldiphenylpropylamine
1954:Journal of Applied Phycology
1521:Hlasiwetz, Heinrich (1855).
1247:type III polyketide synthase
919:
845:. The other two isomers are
7:
3201:Difucofucotetraphlorethol-A
2269:Holz Als Roh- und Werkstoff
1927:Journal of Natural Products
1892:Journal of Natural Products
1274:1,2,3,5-tetrahydroxybenzene
1266:1,2,3,5-tetrahydroxybenzene
733:or concentration (LD, LC):
22:
10:
3381:
2163:10.1007/s12325-022-02347-3
2116:10.1007/s00228-019-02745-7
1834:10.1016/j.bmcl.2006.07.018
1130:phloroglucinol compounds (
434:126.11 g/mol
3336:Halogenated phlorotannins
3335:
3270:
3254:
3228:
3192:Difucofucotriphlorethol-A
3102:
3050:
3014:
2998:
2871:
2798:
2698:
2642:
2612:
2496:
2438:
2429:
2414:
2316:10.1007/s11627-013-9491-2
2072:10.1007/s00228-018-2416-6
1802:: CS1 maint: unfit URL (
1296:Eubacterium oxidoreducens
1211:produces phloroglucinol,
849:(1,2,4-benzenetriol) and
755:
729:
551:
546:
520:
442:colorless to beige solid
399:
379:
344:
74:
66:
54:
49:
21:
3220:Terfucoheptaphlorethol-A
3206:Terfucopentaphlorethol-A
3182:Bisfucoheptaphlorethol-A
3173:Bisfucopentaphlorethol-A
3168:Bisfucotetraphlorethol-A
2993:(tannins in brown algae)
1679:10.15227/orgsyn.015.0070
1615:10.1002/14356007.a19_313
1587:10.15227/orgsyn.009.0074
1539:10.1002/jlac.18550960115
1525:[On phloretin].
1305:Bradyrhizobium japonicum
1287:phloroglucinol reductase
1192:or species in the genus
1111:Dryopteris crassirhizoma
1007:allows the synthesis of
877:by the Austrian chemist
869:Synthesis and occurrence
634:Precautionary statements
3211:Terfucohexaphlorethol-A
1279:Pelobacter acidigallici
1270:1,2,3-trihydroxybenzene
1255:3,5-diketoheptanedioate
1242:Pseudomonas fluorescens
1233:3,5-diketoheptanedioate
1208:Pseudomonas fluorescens
1027:, described in 1988 by
510:Magnetic susceptibility
3163:Bisfucotriphlorethol-A
2031:. EMEA. Archived from
1714:10.1002/anie.198805661
1429:trinitrophloroglucinol
1412:to give a fast black.
1236:
1217:diacetylphloroglucinol
807:
40:
31:
3341:Bromotriphlorethol A1
3293:Phlorofucofuroeckol A
3158:Fucopentaphlorethol-E
3145:Fucotetraphlorethol-B
1556:Thorpe, Edward, ed.,
1523:"Ueber das Phloretin"
1433:1,3,5-trinitrobenzene
1374:inhibitory activity.
1334:and water to produce
1291:dihydrophloroglucinol
1230:
1094:secondary metabolites
1073:, plant extracts and
1011:from phloroglucinol.
802:
39:
30:
2104:Eur J Clin Pharmacol
2060:Eur J Clin Pharmacol
1338:and phloroglucinol.
1308:is able to degrade
1183:Ecklonia stolonifera
1117:Dryopteris filix-mas
1092:Phloroglucinols are
933:'s are 8.5 and 8.9.
56:Preferred IUPAC name
3132:Fucotriphlorethol-B
2853:Cimetropium bromide
2646:serotonin receptors
2151:Advances in Therapy
1939:10.1021/np50055a027
1782:"Coastal Woodfern (
1652:10.1021/ja00056a016
1496:It is also part of
1372:fatty acid synthase
1328:Phloretin hydrolase
1067:potassium hydroxide
1053:Natural occurrences
1045:gives 30% yield of
1025:Pentacarbon dioxide
857:" according to the
804:UV visible spectrum
751:5 g/kg (rat, oral)
459:Solubility in water
60:Benzene-1,3,5-triol
18:
3187:Difucophlorethol-A
3119:Fucodiphlorethol A
2761:Pinaverium bromide
2360:2020-03-05 at the
2281:10.1007/BF02663290
1423:, and explosives (
1378:ATC classification
1312:with formation of
1237:
1142:) can be found in
1019:isovaleroylnitrile
879:Heinrich Hlasiwetz
817:with the formula C
808:
788:Infobox references
41:
32:
16:
3347:
3346:
3089:Pentaphlorethol-B
3072:Tetraphlorethol A
2956:
2955:
2858:Fentonium bromide
2846:Methylscopolamine
2794:
2793:
2614:Phosphodiesterase
2608:
2607:
2004:10.1021/ja042340g
1998:(15): 5332–5333.
1904:10.1021/np030323j
1828:(18): 4738–4742.
1784:Dryopteris arguta
1667:Organic Syntheses
1491:tolonium chloride
1440:condensed tannins
1398:Organic chemicals
1105:Dryopteris arguta
806:of phloroglucinol
796:Chemical compound
794:
793:
600:Hazard statements
313:CompTox Dashboard
116:Interactive image
45:
44:
3372:
3110:Fucophlorethol A
3094:Hexaphlorethol-A
3067:Triphloroethol A
3042:cis-Pentafucol A
2983:
2976:
2969:
2960:
2959:
2841:Butylscopolamine
2816:Tertiary amines:
2716:Chlorbenzoxamine
2473:Oxyphencyclimine
2436:
2435:
2427:
2426:
2395:
2388:
2381:
2372:
2371:
2365:
2351:
2345:
2342:
2336:
2335:
2299:
2293:
2292:
2264:
2258:
2254:
2246:
2240:
2239:
2237:
2235:
2224:
2218:
2217:
2215:
2213:
2207:
2199:
2193:
2192:
2182:
2142:
2136:
2135:
2098:
2092:
2091:
2054:
2048:
2047:
2045:
2043:
2037:
2030:
2022:
2016:
2015:
1987:
1978:
1977:
1949:
1943:
1942:
1922:
1916:
1915:
1887:
1881:
1880:
1852:
1846:
1845:
1817:
1808:
1807:
1801:
1793:
1777:
1771:
1770:
1768:
1766:
1752:
1743:
1742:
1740:
1738:
1724:
1718:
1717:
1689:
1683:
1682:
1662:
1656:
1655:
1640:J. Am. Chem. Soc
1635:
1629:
1628:
1600:
1591:
1590:
1570:
1564:
1554:
1548:
1542:
1518:
1498:Gunzburg reagent
1444:depolymerisation
1189:Eisenia bicyclis
1122:flavaspidic acid
896:
815:organic compound
805:
778:
772:
769:
768:
725:
721:
717:
713:
709:
705:
701:
697:
693:
689:
685:
681:
677:
673:
669:
665:
661:
657:
653:
649:
645:
641:
627:
623:
619:
615:
611:
607:
579:
574:
541:
516:-73.4·10 cm/mol
407:Chemical formula
337:
336:
321:
319:
303:
267:
256:
242:
235:
208:
200:
189:
178:
158:
138:
118:
94:
23:
19:
15:
3380:
3379:
3375:
3374:
3373:
3371:
3370:
3369:
3360:Phloroglucinols
3350:
3349:
3348:
3343:
3331:
3266:
3262:Tetraisofuhalol
3250:
3224:
3103:Fucophlorethols
3098:
3046:
3010:
2994:
2987:
2957:
2952:
2919:
2867:
2807:antimuscarinics
2804:
2803:and derivatives
2802:
2790:
2751:Mentha piperita
2694:
2681:
2658:
2644:
2638:
2615:
2604:
2502:
2499:
2492:
2440:
2431:Antimuscarinics
2421:
2419:
2416:
2410:
2399:
2369:
2368:
2362:Wayback Machine
2352:
2348:
2343:
2339:
2300:
2296:
2265:
2261:
2252:
2247:
2243:
2233:
2231:
2226:
2225:
2221:
2211:
2209:
2208:. Univar Canada
2205:
2201:
2200:
2196:
2143:
2139:
2099:
2095:
2055:
2051:
2041:
2039:
2038:on 10 July 2007
2035:
2028:
2024:
2023:
2019:
1988:
1981:
1950:
1946:
1923:
1919:
1888:
1884:
1853:
1849:
1818:
1811:
1795:
1794:
1778:
1774:
1764:
1762:
1753:
1746:
1736:
1734:
1725:
1721:
1699:
1695:
1690:
1686:
1663:
1659:
1646:(3): 3919–924.
1636:
1632:
1625:
1601:
1594:
1571:
1567:
1555:
1551:
1519:
1515:
1510:
1487:coniferaldehyde
1464:
1406:
1386:section of the
1380:
1344:
1225:
1171:Humulus lupulus
1055:
1005:Hoesch reaction
997:
995:Other reactions
983:
979:
975:
971:
967:
963:
959:
955:
932:
927:
922:
886:trinitrobenzene
871:
835:pharmaceuticals
828:
824:
820:
803:
797:
790:
785:
784:
783: ?)
774:
770:
766:
762:
748:
742:
636:
602:
588:
567:
530:
513:
499:
461:
423:
419:
415:
409:
395:
392:
391:c1c(cc(cc1O)O)O
387:
386:
375:
372:
371:
368:
362:
361:
358:
352:
351:
340:
322:
315:
306:
286:
270:
257:
245:
218:
181:
161:
141:
121:
108:
97:
84:
70:
62:
61:
17:Phloroglucinol
12:
11:
5:
3378:
3368:
3367:
3362:
3345:
3344:
3339:
3337:
3333:
3332:
3330:
3329:
3324:
3319:
3314:
3309:
3304:
3299:
3290:
3285:
3280:
3274:
3272:
3268:
3267:
3265:
3264:
3258:
3256:
3252:
3251:
3249:
3248:
3246:Tetrafuhalol A
3243:
3238:
3232:
3230:
3226:
3225:
3223:
3222:
3217:
3208:
3203:
3198:
3189:
3184:
3179:
3170:
3165:
3160:
3155:
3142:
3129:
3116:
3106:
3104:
3100:
3099:
3097:
3096:
3091:
3086:
3069:
3064:
3062:diphlorethol A
3054:
3052:
3048:
3047:
3045:
3044:
3039:
3034:
3029:
3024:
3018:
3016:
3012:
3011:
3009:
3008:
3006:Phloroglucinol
3002:
3000:
2996:
2995:
2986:
2985:
2978:
2971:
2963:
2954:
2953:
2951:
2950:
2945:
2940:
2935:
2934:
2933:
2928:
2917:
2912:
2911:
2910:
2908:Metoclopramide
2905:
2900:
2895:
2890:
2877:
2875:
2869:
2868:
2866:
2865:
2863:Methylatropine
2860:
2855:
2850:
2849:
2848:
2843:
2838:
2827:
2826:
2821:
2812:
2810:
2796:
2795:
2792:
2791:
2789:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2756:Phloroglucinol
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2713:
2708:
2702:
2700:
2696:
2695:
2693:
2692:
2691:
2690:
2679:
2674:
2673:
2672:
2667:
2656:
2650:
2648:
2640:
2639:
2637:
2636:
2631:
2626:
2620:
2618:
2610:
2609:
2606:
2605:
2603:
2602:
2597:
2592:
2587:
2582:
2577:
2572:
2567:
2562:
2557:
2552:
2547:
2542:
2537:
2532:
2530:Glycopyrronium
2527:
2522:
2517:
2512:
2506:
2504:
2494:
2493:
2491:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2444:
2442:
2433:
2424:
2412:
2411:
2398:
2397:
2390:
2383:
2375:
2367:
2366:
2346:
2337:
2294:
2259:
2241:
2219:
2194:
2157:(2): 619–640.
2137:
2093:
2066:(5): 541–548.
2049:
2017:
1979:
1944:
1917:
1898:(1): 103–105.
1882:
1863:(9): 813–824.
1847:
1809:
1790:GlobalTwitcher
1772:
1744:
1719:
1708:(4): 566–568.
1697:
1693:
1684:
1657:
1630:
1624:978-3527306732
1623:
1592:
1565:
1549:
1533:(1): 118–123.
1512:
1511:
1509:
1506:
1463:
1460:
1405:
1402:
1379:
1376:
1352:spasmodic pain
1343:
1342:Health effects
1340:
1224:
1221:
1205:The bacterium
1158:St John's wort
1140:sideroxylonals
1054:
1051:
1043:phloretic acid
996:
993:
986:
985:
981:
977:
973:
969:
965:
961:
957:
953:
930:
926:
923:
921:
918:
898:
897:
870:
867:
826:
822:
818:
811:Phloroglucinol
795:
792:
791:
786:
764:
763:
759:standard state
756:
753:
752:
749:
740:
738:
735:
734:
727:
726:
680:P305+P351+P338
637:
632:
629:
628:
603:
598:
595:
594:
589:
584:
581:
580:
568:
563:
560:
559:
549:
548:
544:
543:
531:
526:
523:
522:
518:
517:
514:
508:
505:
504:
501:
497:
487:
486:
472:
466:
465:
462:
457:
454:
453:
450:
444:
443:
440:
436:
435:
432:
426:
425:
421:
417:
413:
410:
405:
402:
401:
397:
396:
394:
393:
390:
382:
381:
380:
377:
376:
374:
373:
369:
366:
365:
363:
359:
356:
355:
347:
346:
345:
342:
341:
339:
338:
325:
323:
311:
308:
307:
305:
304:
296:
294:
288:
287:
285:
284:
280:
278:
272:
271:
269:
268:
260:
258:
250:
247:
246:
244:
243:
236:
228:
226:
220:
219:
217:
216:
212:
210:
202:
201:
191:
183:
182:
180:
179:
171:
169:
163:
162:
160:
159:
151:
149:
143:
142:
140:
139:
131:
129:
123:
122:
120:
119:
111:
109:
102:
99:
98:
96:
95:
87:
85:
80:
77:
76:
72:
71:
68:
64:
63:
59:
58:
52:
51:
47:
46:
43:
42:
33:
9:
6:
4:
3:
2:
3377:
3366:
3363:
3361:
3358:
3357:
3355:
3342:
3338:
3334:
3328:
3325:
3323:
3322:8,4"'-Dieckol
3320:
3318:
3317:7-Phloroeckol
3315:
3313:
3310:
3308:
3307:3-Phloroeckol
3305:
3303:
3302:2-Phloroeckol
3300:
3298:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3275:
3273:
3269:
3263:
3260:
3259:
3257:
3253:
3247:
3244:
3242:
3239:
3237:
3234:
3233:
3231:
3227:
3221:
3218:
3216:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3150:
3146:
3143:
3141:
3137:
3133:
3130:
3128:
3124:
3120:
3117:
3115:
3111:
3108:
3107:
3105:
3101:
3095:
3092:
3090:
3087:
3085:
3081:
3077:
3073:
3070:
3068:
3065:
3063:
3059:
3056:
3055:
3053:
3049:
3043:
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3019:
3017:
3013:
3007:
3004:
3003:
3001:
2997:
2992:
2991:phlorotannins
2984:
2979:
2977:
2972:
2970:
2965:
2964:
2961:
2949:
2946:
2944:
2941:
2939:
2936:
2932:
2929:
2927:
2924:
2923:
2922:
2921:
2913:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2885:
2884:
2883:
2879:
2878:
2876:
2874:
2870:
2864:
2861:
2859:
2856:
2854:
2851:
2847:
2844:
2842:
2839:
2837:
2834:
2833:
2832:
2829:
2828:
2825:
2822:
2820:
2817:
2814:
2813:
2811:
2808:
2801:
2797:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2746:Isometheptene
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2703:
2701:
2697:
2689:
2686:
2685:
2684:
2683:
2675:
2671:
2668:
2666:
2663:
2662:
2661:
2660:
2652:
2651:
2649:
2647:
2641:
2635:
2632:
2630:
2627:
2625:
2622:
2621:
2619:
2617:
2611:
2601:
2600:Tridihexethyl
2598:
2596:
2593:
2591:
2588:
2586:
2585:Propantheline
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2551:
2550:Methantheline
2548:
2546:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2525:Fenpiverinium
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2507:
2505:
2501:
2495:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2453:Dicycloverine
2451:
2449:
2446:
2445:
2443:
2437:
2434:
2432:
2428:
2425:
2423:
2413:
2408:
2404:
2396:
2391:
2389:
2384:
2382:
2377:
2376:
2373:
2363:
2359:
2356:
2350:
2341:
2333:
2329:
2325:
2321:
2317:
2313:
2309:
2305:
2298:
2290:
2286:
2282:
2278:
2274:
2270:
2263:
2257:
2251:
2245:
2229:
2223:
2204:
2198:
2190:
2186:
2181:
2176:
2172:
2168:
2164:
2160:
2156:
2152:
2148:
2141:
2133:
2129:
2125:
2121:
2117:
2113:
2109:
2105:
2097:
2089:
2085:
2081:
2077:
2073:
2069:
2065:
2061:
2053:
2034:
2027:
2021:
2013:
2009:
2005:
2001:
1997:
1993:
1986:
1984:
1975:
1971:
1967:
1963:
1959:
1955:
1948:
1940:
1936:
1932:
1928:
1921:
1913:
1909:
1905:
1901:
1897:
1893:
1886:
1878:
1874:
1870:
1866:
1862:
1858:
1851:
1843:
1839:
1835:
1831:
1827:
1823:
1816:
1814:
1805:
1799:
1791:
1787:
1785:
1776:
1760:
1759:
1751:
1749:
1732:
1731:
1723:
1715:
1711:
1707:
1703:
1688:
1680:
1676:
1672:
1668:
1661:
1653:
1649:
1645:
1641:
1634:
1626:
1620:
1616:
1612:
1608:
1607:
1599:
1597:
1588:
1584:
1580:
1576:
1569:
1563:
1559:
1553:
1546:
1540:
1536:
1532:
1528:
1524:
1517:
1513:
1505:
1503:
1499:
1494:
1492:
1488:
1484:
1479:
1477:
1473:
1469:
1459:
1455:
1453:
1449:
1445:
1441:
1436:
1434:
1430:
1426:
1422:
1418:
1413:
1411:
1401:
1399:
1396:
1392:
1389:
1385:
1375:
1373:
1368:
1366:
1362:
1361:gynecological
1358:
1353:
1349:
1339:
1337:
1333:
1329:
1325:
1323:
1322:hydroxyquinol
1319:
1315:
1311:
1307:
1306:
1300:
1298:
1297:
1292:
1288:
1283:
1281:
1280:
1275:
1271:
1267:
1263:
1258:
1256:
1252:
1248:
1244:
1243:
1234:
1229:
1220:
1218:
1214:
1210:
1209:
1203:
1201:
1200:phlorotannins
1197:
1196:
1191:
1190:
1185:
1184:
1179:
1175:
1173:
1172:
1167:
1163:
1159:
1155:
1151:
1147:
1146:
1141:
1137:
1133:
1129:
1125:
1123:
1119:
1118:
1113:
1112:
1107:
1106:
1101:
1097:
1095:
1090:
1088:
1084:
1080:
1076:
1072:
1068:
1064:
1060:
1050:
1048:
1044:
1039:
1036:
1034:
1030:
1026:
1022:
1020:
1016:
1015:Leptospermone
1012:
1010:
1006:
1001:
992:
989:
951:
950:
949:
947:
943:
939:
934:
917:
915:
911:
907:
903:
895:
891:
890:
889:
887:
882:
881:(1825–1875).
880:
876:
866:
864:
860:
856:
852:
848:
847:hydroxyquinol
844:
843:benzenetriols
840:
836:
832:
816:
812:
801:
789:
782:
777:
760:
754:
750:
746:
737:
736:
732:
728:
638:
635:
631:
630:
604:
601:
597:
596:
593:
590:
587:
583:
582:
578:
573:
569:
566:
562:
561:
557:
555:
550:
545:
540:
535:
532:
529:
525:
524:
521:Pharmacology
519:
515:
511:
507:
506:
502:
496:
492:
489:
488:
485:
481:
477:
476:diethyl ether
473:
471:
468:
467:
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448:Melting point
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188:ECHA InfoCard
185:
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48:
38:
34:
29:
25:
24:
20:
3327:8,8′-Bieckol
3312:6,6'-Bieckol
3241:Trifuhalol A
3058:Diphlorethol
3037:Tetrafucol B
3032:Tetrafucol A
3005:
2914:
2880:
2830:
2815:
2755:
2721:Diisopromine
2676:
2653:
2560:Oxyphenonium
2540:Isopropamide
2478:Piperidolate
2463:Dihexyverine
2349:
2340:
2307:
2303:
2297:
2272:
2268:
2262:
2244:
2232:. Retrieved
2222:
2210:. Retrieved
2197:
2154:
2150:
2140:
2107:
2103:
2096:
2063:
2059:
2052:
2040:. Retrieved
2033:the original
2020:
1995:
1991:
1957:
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1947:
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1926:
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1895:
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1885:
1860:
1856:
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1825:
1821:
1789:
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1763:. Retrieved
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1735:. Retrieved
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1530:
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1516:
1495:
1480:
1465:
1462:Use in tests
1456:
1452:Phlobaphenes
1442:by means of
1437:
1414:
1407:
1404:Applications
1397:
1390:
1388:ATC code A03
1383:
1381:
1369:
1345:
1326:
1303:
1301:
1294:
1284:
1277:
1259:
1251:malonyl-CoAs
1240:
1238:
1223:Biosynthesis
1206:
1204:
1193:
1187:
1181:
1176:
1169:
1154:adhyperforin
1143:
1136:macrocarpals
1126:
1115:
1109:
1103:
1098:
1091:
1087:phlobaphenes
1056:
1040:
1037:
1029:GĂĽnter Maier
1023:
1013:
1002:
998:
990:
987:
968:OH → (CH
935:
928:
899:
883:
872:
810:
809:
730:
591:
553:
494:
276:RTECS number
156:ChEMBL473159
75:Identifiers
67:Other names
3288:Eckstolonol
3255:Isofuhalols
3051:Phlorethols
2926:Cinitapride
2903:Domperidone
2873:Propulsives
2836:Scopolamine
2824:Hyoscyamine
2781:Trepibutone
2776:Tiropramide
2741:Idanpramine
2670:Cilansetron
2659:antagonists
2624:Drotaverine
2570:Pipenzolate
2565:Penthienate
2545:Mepenzolate
2535:Hexocyclium
2488:Trimebutine
2441:amino group
2310:(1): 1–16.
1933:: 158–160.
1765:26 December
1737:26 December
1470:' test for
1448:nucleophile
1417:Flopropione
1285:The enzyme
1260:The enzyme
1178:Brown algae
863:polyphenols
745:median dose
731:Lethal dose
586:Signal word
474:soluble in
464:1 g/100 mL
439:Appearance
400:Properties
194:100.003.284
136:CHEBI:16204
3365:Triketones
3354:Categories
2943:Ilebopride
2938:Acotiamide
2898:Clebopride
2893:Bromopride
2888:Alizapride
2800:Belladonna
2771:Simeticone
2736:Fenpiprane
2731:Fenoverine
2711:Caroverine
2634:Papaverine
2629:Moxaverine
2616:inhibitors
2595:Timepidium
2520:Diphemanil
2498:Quaternary
2483:Rociverine
2468:Mebeverine
2458:Difemerine
2418:functional
2401:Drugs for
2275:(5): 212.
2110:(1): 1–6.
1960:(4): 291.
1575:Org. Synth
1508:References
1458:rooting.
1410:diazo dyes
1348:gallstones
1336:phloretate
1318:resorcinol
1231:Activated
1180:, such as
1166:isoprenoid
1150:Hyperforin
1145:Eucalyptus
1128:Formylated
1071:glucosides
914:hydrolysis
851:pyrogallol
839:explosives
565:Pictograms
470:Solubility
430:Molar mass
301:DHD7FFG6YS
167:ChemSpider
103:3D model (
82:CAS Number
3236:Bifuhalol
2989:Types of
2948:Mosapride
2931:Cisapride
2766:Proxazole
2688:Mosapride
2665:Alosetron
2643:Acting on
2590:Tiemonium
2580:Prifinium
2555:Otilonium
2510:Benzilone
2503:compounds
2448:Camylofin
2422:disorders
2415:Drugs for
2324:1475-2689
2171:1865-8652
2132:201103441
1421:Phloretin
1357:obstetric
1332:phloretin
1148:species.
1132:euglobals
1079:quercetin
1063:phloretin
1059:flavonoid
1047:phloretin
1033:pyrolysis
942:tautomers
920:Reactions
906:hydroxide
875:phloretin
831:synthesis
716:P403+P233
704:P337+P313
700:P333+P313
696:P332+P313
684:P308+P313
676:P304+P340
672:P302+P352
556:labelling
283:UX1050000
215:203-611-2
207:EC Number
3229:Fuhalols
3027:Trifucol
2920:agonists
2819:Atropine
2706:Alverine
2682:agonists
2515:Bevonium
2500:ammonium
2439:Tertiary
2358:Archived
2332:15470904
2256:15629637
2234:24 April
2212:24 April
2189:36443585
2124:31435708
2080:29350249
2042:24 April
2012:15826166
1974:13479924
1912:14738398
1877:10913843
1842:16870425
1798:cite web
1502:vanillin
1476:furfural
1472:pentoses
1310:catechin
1162:Humulone
1083:catechin
1077:such as
547:Hazards
542:)
528:ATC code
512:(χ)
484:pyridine
92:108-73-6
3278:Dieckol
3022:Difucol
2999:Monomer
2575:Poldine
2355:article
2289:6585979
2180:9898402
2088:4700542
1468:Tollens
1195:Zonaria
976:(C=NOH)
964:+ 3 NH
902:aniline
855:phenols
781:what is
779: (
592:Warning
536: (
534:A03AX12
491:Acidity
480:ethanol
424:
252:PubChem
3271:Eckols
3015:Fucols
2420:bowel
2330:
2322:
2287:
2253:
2187:
2177:
2169:
2130:
2122:
2086:
2078:
2010:
1972:
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1840:
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1621:
1581:: 74.
1483:lignin
1108:or in
1075:resins
980:+ 3 H
936:As an
813:is an
776:verify
773:
384:SMILES
240:C02183
233:D00152
147:ChEMBL
50:Names
3283:Eckol
2699:Other
2328:S2CID
2285:S2CID
2250:INIST
2206:(PDF)
2128:S2CID
2084:S2CID
2036:(PDF)
2029:(PDF)
1970:S2CID
1330:uses
1289:uses
1264:uses
946:oxime
910:imine
859:IUPAC
503:8.45
349:InChI
127:ChEBI
105:JSmol
3295:and
3213:and
3194:and
3175:and
3151:and
3138:and
3125:and
3112:and
3082:and
3060:and
2916:5-HT
2678:5-HT
2655:5-HT
2320:ISSN
2236:2009
2214:2009
2185:PMID
2167:ISSN
2120:PMID
2076:PMID
2044:2009
2008:PMID
1908:PMID
1873:PMID
1838:PMID
1804:link
1767:2016
1739:2016
1619:ISBN
1562:183.
1425:TATB
1359:and
1320:and
1268:and
1215:and
1152:and
1138:and
1100:Acyl
1085:and
1003:The
960:(OH)
938:enol
837:and
825:(OH)
724:P501
720:P405
712:P363
708:P362
692:P321
688:P312
668:P281
664:P280
660:P272
656:P271
652:P264
648:P261
644:P202
640:P201
626:H361
622:H341
618:H335
614:H319
610:H317
606:H315
292:UNII
224:KEGG
2407:A03
2312:doi
2277:doi
2175:PMC
2159:doi
2112:doi
2068:doi
2000:doi
1996:127
1962:doi
1935:doi
1900:doi
1865:doi
1830:doi
1710:doi
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833:of
554:GHS
539:WHO
318:EPA
265:359
255:CID
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