338:
199:
530:
27:
525:
36:
1294:
821:(1846–1927). Thus Eijkman inferred the correct basic structure for shikimol. He also noted that shikimol and safrole had the same empirical formula and had other similar properties, and thus he suggested that they were probably identical. In 1886, Poleck showed that upon oxidation, safrole also formed piperonylic acid, and thus shikimol and safrole were indeed identical. It remained to be determined whether the molecule's C
1359:. However, it is not clear what proportion of illicitly harvested safrole is going toward MDMA production, as over 90% of the global safrole supply (about 2,000 tonnes or 2,200 short tons per year) is used to manufacture pesticides, fragrances, and other chemicals. Sustainable harvesting of safrole is possible from leaves and stems of certain plants, including the roots of camphor seedlings.
632:
1053:(ecstasy). When safrole is metabolized several metabolites can be identified. Some of these metabolites have been shown to exhibit toxicological effects, such as 1′-hydroxysafrole and 3′-hydroxysafrole in rats. Further metabolites of safrole that have been found in urine of both rats and humans include 1,2-dihydroxy-4-allylbenzene or 1(2)-methoxy-2(1)hydroxy-4-allylbenzene.
1239:
According to a 1977 study of the metabolites of safrole in both rats and humans, two carcinogenic metabolites of safrole found in the urine of rats, 1′-hydroxysafrole and 3′-hydroxyisosafrole, were not found in human urine. The
European Commission on Health and consumer protection assumes safrole to
2473:
MacFabe, Derrick F.; Cain, Donald P.; Rodriguez-Capote, Karina; Franklin, Andrew E.; Hoffman, Jennifer E.; Boon, Francis; Taylor, A. Roy; Kavaliers, Martin; Ossenkopp, Klaus-Peter (2007-01-10). "Neurobiological effects of intraventricular propionic acid in rats: Possible role of short chain fatty
2429:
Jeurissen, Suzanne M. F.; Bogaards, Jan J. P.; Awad, Hanem M.; Boersma, Marelle G.; Brand, Walter; Fiamegos, Yiannis C.; van Beek, Teris A.; Alink, Gerrit M.; Sudhölter, Ernst J. R. (2004-09-01). "Human cytochrome p450 enzyme specificity for bioactivation of safrole to the proximate carcinogen
1336:
contains a low percentage of steam-volatile oil, which is typically 75% safrole. Attempts to refine safrole from sassafras bark in mass quantities are generally not economically viable due to low yield and high effort. However, smaller quantities can be extracted quite easily via
1104:
is a minor metabolite of safrole in humans, mice, and rats. The intact allyl side chain of allylcatechol may then be oxidized to yield 2′,3′-epoxypropylcatechol. This can serve as a substrate for an epoxide hydratase enzyme, and will hydrate the 2′,3′-epoxypropylcatechol to
1272:
against bacteria. In addition to the inhibition of the defensive function of neutrophils, it has also been discovered that safrole interferes with the formation of superoxides by neutrophils. Furthermore, safrole oxide, a metabolite of safrole, has a negative effect on the
1121:
activity. The epoxide of allylcatechol may also be generated from the cleavage of the methylenedioxy group of the safrole epoxide. The cleavage of the methylenedioxy ring and the metabolism of the allyl group involve hepatic microsomal mixed-function oxidases.
919:. After filtering-off the calcium chloride, the oil is vacuum distilled at 100 °C under a vacuum of 11 mmHg (1.5 kPa) or frozen to crystallize the safrole out. This technique works with other oils in which safrole is present as well.
1306:
813:(1851–1915) investigated shikimol, the essential oil that is obtained from Japanese star anise, and he found that, upon oxidation, shikimol formed piperonylic acid, whose basic structure had been determined in 1871 by the German chemist
2710:
Su, Le; Zhao, BaoXiang; Lv, Xin; Wang, Nan; Zhao, Jing; Zhang, ShangLi; Miao, JunYing (2007-02-20). "Safrole oxide induces neuronal apoptosis through inhibition of integrin β4/SOD activity and elevation of ROS/NADPH oxidase activity".
1193:, while the methylenedioxy group is associated with changes in the cytochrome P450 system and epigenetic aspects of carcinogenicity. In rats, safrole and related compounds produced both benign and malignant
1048:
Isosafrole is produced synthetically from safrole. It is not found in nature. Isosafrole comes in two forms, trans-isosafrole and cis-isosafrole. Isosafrole is used as a precursor for the psychoactive drug
538:
2226:
Lages, A. S.; Silva, K. C.; Miranda, A. L.; Fraga, C. A.; Barreiro, E. J. (1998-01-20). "Synthesis and pharmacological evaluation of new flosulide analogues, synthesized from natural safrole".
1268:
Besides being a hepatocarcinogen, safrole exhibits further adverse effects in that it will induce the formation of hepatic lipid hydroperoxides. Safrole also inhibits the defensive function of
1256:. In that role, safrole, like many naturally-occurring compounds, may have a small but measurable ability to induce cancer in rodents. Despite this, the effects in humans were estimated by the
505:
2269:
Lima, L.M.; Amarante, E.G.; Miranda, A.L.P.; Fraga, C.A.M.; Barreiro, E.J. (1999). "Synthesis and
Antinociceptive Profile of Novel Acidic Sulphonylhydrazone Derivatives From Natural Safrole".
2641:
Opinion of the
Scientific Committee on Food on the safety of the presence of safrole (1-allyl-3,4-methylenedioxybenzene) in flavourings and other food ingredients with flavouring properties
1224:, causing permanent liver damage in rats; food products sold there purporting to contain sassafras instead contain a safrole-free sassafras extract. Safrole is also banned for use in
2004:
Wisneski, Harris H.; Yates, Ronald L.; Davis, Henry M. (1983). "High-performance liquid chromatographic—fluorometric determination of safrole in perfume, cologne and toilet water".
2534:
Hagan, Ernest C.; Jenner, Paul M.; Jones, Wm.I.; Fitzhugh, O.Garth; Long, Eleanor L.; Brouwer, J.G.; Webb, Willis K. (1965). "Toxic properties of compounds related to safrole".
1085:. So far, this has only been found in rats and guinea pigs. The formed epoxide is a small metabolite due to the slow formation and further metabolism of the compound. An
915:
of the root bark of the sassafras tree. The resulting steam distilled product contains about 90% safrole by weight. The oil is dried by mixing it with a small amount of
1420:
779:
1092:
The metabolism of safrole through the oxidation of the methylenedioxy proceeds via the cleavage of the methylenedioxy group. This results in two major metabolites:
2179:
Lima, P. C.; Lima, L. M.; da Silva, K. C.; Léda, P. H.; de
Miranda, A. L.; Fraga, C. A.; Barreiro, E. J. (2000-02-01). "Synthesis and analgesic activity of novel
1415:[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
2296:
Fraga, Carlos A. M.; Barreiro, Eliezer J. (1992-10-01). "The synthesis of a new benzothiazine derivative, related to oxicams, synthesized from natural safrole".
1086:
1170:. The formation of this complex leads to lower amounts of available free cytochrome P450. Safrole can also directly bind to cytochrome P450, leading to
1097:
645:
610:
1167:
1082:
2077:
Zhao, Jing; Miao, Junying; Zhao, Baoxiang; Zhang, Shangli; Yin, Deling (2005-06-01). "Safrole oxide inhibits angiogenesis by inducing apoptosis".
3037:
3027:
1093:
3067:
1341:(about 10% of dry sassafras root bark by mass, or about 2% of fresh bark). Demand for safrole is causing rapid and illicit harvesting of the
1040:-acylarylhydrazones, isosters, aryl-sulfonamide derivatives, acidic sulfonylhydrazone derivatives, benzothiazine derivatives. and many more.
2336:
Ioannides, C.; Delaforge, M.; Parke, D. V. (1981-10-01). "Safrole: its metabolism, carcinogenicity and interactions with cytochrome P-450".
3017:
387:
3022:
2992:
2967:
2675:
Liu, T. Y.; Chen, C. C.; Chen, C. L.; Chi, C. W. (1999-07-01). "Safrole-induced
Oxidative Damage in the Liver of Sprague–Dawley Rats".
2034:
Hung, Shan-Ling; Chen, Yu-Ling; Chen, Yen-Ting (2003-04-01). "Effects of safrole on the defensive functions of human neutrophils".
790:(1835–1900) and J. Ruotte investigated and named safrole. They observed its reaction with bromine, suggesting the presence of an
2931:
1918:
Kamdem, Donatien; Gage, Douglas (1995-12-01). "Chemical
Composition of Essential Oil from the Root Bark of Sassafras albidum".
955:
2886:
2569:
Liu, T.Y.; Chen, C.C.; Chen, C.L.; Chi, C.W. (1999). "Safrole-induced
Oxidative Damage in the Liver of Sprague–Dawley Rats".
1257:
1412:
1233:
1069:
complex, which will transform safrole into 1′-hydroxysafrole. The newly formed 1′-hydroxysafrole will undergo a phase II
3118:
1408:
889:
2800:
352:
2748:
1847:
2606:
Benedetti, M; Malnoe, A; Broillet, A (1977). "Absorption, metabolism and excretion of safrole in the rat and man".
640:
652:
2824:
2386:
Sekizawa, J.; Shibamoto, T. (1982-04-01). "Genotoxicity of safrole-related chemicals in microbial test systems".
1134:
at higher doses in rats and mice. Safrole requires metabolic activation before exhibiting toxicological effects.
1065:
side chain and the oxidation of the methylenedioxy group. The oxidation of the allyl side chain is mediated by a
595:
2764:
Regulation (EC) No 273/2004 of the
European Parliament and of the Council of 11 February 2004 on drug precursors
1525:
Die Ätherischen Öle nach ihren chemischen
Bestandteilen unter Berücksichtigung der geschichtlichen Entwicklung
1581:
1557:
1413:"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
983:
26:
703:
plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural
3103:
2571:
1715:"Untersuchungen über die Constitution des Piperins und seiner Spaltungsproducte Piperinsäure und Piperidin"
1416:
1217:
574:
285:
194:
35:
2924:
1752:
1714:
316:
156:
1784:
529:
2763:
1642:
524:
1674:
116:
2790:
1961:
Hickey, M. J. (1948-05-01). "Investigation of the chemical constituents of
Brazilian sassafras oil".
1815:
1444:
Kamdem, Donatien; Gage, Douglas (2007). "Chemical Composition of Essential Oil from the Root Bark of
1181:
Furthermore, because of the altered structural and functional properties of cytochrome P450, loss of
1110:
206:
1530:
The volatile oils according to their chemical components with regard to their historical development
1486:
Hickey, Michael J. (1948). "Investigation of the chemical constituents of Brazilian sassafras oil".
3113:
1343:
1131:
333:
1197:
after intake through the mouth. Changes in the liver are also observed through the enlargement of
1142:
in safrole is able to produce intermediates which are directly capable of binding covalently with
3098:
2874:
810:
482:
2120:
Perkin, William Henry; Trikojus, Victor Martin (1927-01-01). "CCXII.—A synthesis of safrole and
3108:
2917:
1307:
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
1274:
1171:
1118:
1014:
896:
814:
2904:
2517:
O'Mathuna, Donal (10 August 2010). "Does it work? Can sassafras be used as a general tonic?".
1523:
695:. It is a colorless oily liquid, although impure samples can appear yellow. A member of the
176:
1546:
Les professeurs des facultés des lettres et des sciences en france au xixe siècle (1808–1880)
1326:
1302:
1260:
to be similar to risks posed by breathing indoor air or drinking municipally supplied water.
1186:
1159:
731:
552:
517:
2155:
1061:
Safrole can undergo many forms of metabolism. The two major routes are the oxidation of the
970:
synergists; for example, safrole is used as a precursor in the synthesis of the insecticide
966:
Safrole is a member of the methylenedioxybenzene group, of which many compounds are used as
954:. Safrole can be detected in undiluted liquid beverages and pharmaceutical preparations by
294:
48:
1891:
Perkin, William Henry; Trikojus, Victor Martin (1927). "CCXII.—A synthesis of safrole and
1543:
8:
588:
82:
934:, a Brazilian species. Safrole is also present in certain essentials oils and in brown
337:
198:
92:
2499:
1352:
1338:
1322:
971:
912:
739:
727:, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
136:
2688:
2584:
2239:
2196:
2017:
849:). In 1888, the German chemist Julius Wilhelm Brühl (1850–1911) determined that the C
787:
762:
Safrole was obtained from a number of plants, but especially from the sassafras tree (
3052:
2882:
2850:
2796:
2728:
2692:
2623:
2619:
2588:
2551:
2547:
2491:
2455:
2447:
2411:
2403:
2399:
2361:
2353:
2349:
2313:
2251:
2243:
2208:
2200:
2137:
2102:
2094:
2059:
2051:
2047:
1986:
1978:
1943:
1935:
1503:
1465:
1216:, sassafras tea, and other common goods, but was banned for human consumption by the
987:
924:
901:
881:
783:
770:
764:
719:
1089:
enzyme will act on the epoxide to form dihydrodiol, which can be secreted in urine.
3072:
2720:
2684:
2640:
2615:
2580:
2543:
2503:
2483:
2439:
2395:
2345:
2305:
2278:
2235:
2192:
2129:
2086:
2043:
2013:
1970:
1927:
1900:
1827:
1796:
1738:
1694:
1654:
1495:
1457:
1240:
be genotoxic and carcinogenic. It occurs naturally in a variety of spices, such as
1109:(PPA), which is a substance that is related to an increase in oxidative stress and
1074:
1029:
first by conversion to methylenedioxybenzene, which is brominated and coupled with
930:
916:
668:
410:
1848:"Refusal to Extend Effective Date of Statute for Certain Specified Food Additives"
1532:] (in German). Vol. 4. Leipzig, Germany: Veit & Co. pp. 139–144.
2775:
2752:
1163:
1070:
1066:
907:
871:
709:
696:
258:
1189:
through cytochrome P450 may occur. The allyl group thus directly contributes to
3047:
2652:
2282:
1348:
1151:
1106:
975:
795:
623:
2724:
2487:
2090:
1800:
3092:
2949:
2941:
2855:
2474:
acids on the pathogenesis and characteristics of autism spectrum disorders".
2451:
2407:
2357:
2317:
2247:
2204:
2141:
2098:
2055:
1982:
1939:
1831:
1742:
1698:
1658:
1209:
1030:
724:
471:
461:
187:
2779:, 13th edition, Merck & Co, Inc, Whitehorse Station, NJ, copyright 2001.
2309:
1890:
938:, which is present in small amounts in many plants. Safrole can be found in
584:
2732:
2696:
2592:
2555:
2495:
2459:
2212:
2106:
2063:
1990:
1722:
1507:
1277:. Safrole oxide inhibits the expression of integrin β4/SOD, which leads to
1249:
1221:
951:
892:
is usually devoid of safrole due to a rule passed by the U.S. FDA in 1960.
2909:
2415:
2365:
2255:
1947:
1931:
1469:
1461:
990:
for its characteristic ‘candy-shop’ aroma. It was used as an additive in
3062:
2745:
2519:
2133:
1904:
1393:
1139:
1105:
2′,3′-dihydroxypropylcatechol. This new compound can be oxidized to form
1078:
1010:
995:
967:
838:
791:
735:
704:
2627:
1974:
1499:
982:, 3,4-methylenedioxymethamphetamine). Before safrole was banned by the
928:(native to eastern North America) in the form of sassafras oil, or from
3057:
3042:
3032:
2997:
2982:
1726:
1314:
1282:
1269:
1202:
1198:
1135:
999:
818:
747:
438:
207:
167:
2443:
1293:
3007:
1439:
1437:
1373:
1368:
1333:
1318:
1278:
1213:
991:
743:
700:
580:
305:
622:
Except where otherwise noted, data are given for materials in their
3002:
2987:
2977:
2957:
2825:"Harvested to make Ecstasy, Cambodia's trees are felled one by one"
2472:
1718:
1356:
1241:
1182:
1026:
974:. Safrole is also used as a precursor in the synthesis of the drug
947:
830:
768:), which is native to North America, and from Japanese star anise (
233:
1434:
922:
Safrole is typically extracted from the root-bark or the fruit of
562:
115:
3012:
2972:
2183:-acylarylhydrazones and isosters, derived from natural safrole".
1229:
1190:
1175:
1155:
1147:
1101:
1081:. A different oxidation pathway of the allyl side chain can form
1036:
Safrole is a versatile precursor to many compounds. Examples are
935:
866:
803:
799:
451:
361:
InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
245:
1818:[Investigations of the terpenes and their derivatives].
371:
InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
2962:
2905:
EU Narcotic drugs and psychotropic substances: internal aspects
1321:
are Category I precursors under regulation no. 273/2004 of the
1245:
943:
876:
714:
147:
1857:. United States Food & Drug Administration. p. 12412
1253:
1194:
1062:
939:
269:
127:
105:
2428:
1560:[Investigations of the essential oil of sassafras].
321:
1310:
1225:
1050:
1003:
979:
751:
476:
232 to 234 °C (450 to 453 °F; 505 to 507 K)
224:
1596:"Ils sont constitués par une principe oxygéné, la safrol C
1610:(They are composed of an oxygenated substance, safrole C
1174:. These two mechanisms result in lowered mixed function
1143:
2533:
2268:
1130:
Toxicological studies have shown that safrole is a weak
1117:
activity. PPA also causes a decrease in glutathione and
2605:
2335:
1816:"Untersuchungen über die Terpene und deren Abkömmlinge"
1544:
http://facultes19.ish-lyon.cnrs.fr/fiche.php?indice=456
798:(1821–1906) suggested that safrole was a derivative of
2875:"Piper hispidinervum: A Sustainable Source of Safrole"
2225:
1220:
after studies in the 1960s suggested that safrole was
2881:. Alexandria, Virginia: ASHS Press. pp. 479–81.
2178:
1077:
enzyme to create 1′-sulfoxysafrole, which can cause
2653:"Ranking Possible Cancer Hazards on the HERP Index"
2003:
1645:[On the chemical composition of safrole].
817:(1835–1910) and his student, the American chemist
558:
2385:
2156:"Synthesis of Safrole - [www.rhodium.ws]"
2076:
1558:"Recherches sur l'huile essentielle de sassafras"
3090:
1787:[On the chemical structure of safrole].
1212:, it was once widely used as a food additive in
257:
2844:
2842:
2029:
2027:
1520:The history of research on safrole appears in:
1325:. In the United States, safrole is currently a
91:
2674:
2568:
2119:
1820:Berichte der Deutschen Chemischen Gesellschaft
1789:Berichte der Deutschen Chemischen Gesellschaft
1647:Berichte der Deutschen Chemischen Gesellschaft
1643:"Ueber die chemische Constitution des Safrols"
750:, and the empathogenic/entactogenic substance
566:
2925:
2516:
2295:
1584:[On the essential oil of sassafras].
1579:
2868:
2866:
2839:
2709:
2228:Bioorganic & Medicinal Chemistry Letters
2033:
2024:
1717:[Investigations into the composition of
1712:
1481:
1479:
865:Safrole is the principal component of brown
2939:
2873:Rocha, Sérgio F.R.; Ming, Lin Chau (1999).
2795:(2nd ed.). UVKCHEM, Inc. p. 206.
1006:, and certain pharmaceutical preparations.
911:. Sassafras oil for example is obtained by
802:, to which two oxygen atoms were joined as
699:family of natural products, it is found in
2932:
2918:
1917:
1785:"Ueber die chemische Structur des Safrols"
1687:Recueil des Travaux Chimiques des Pays-Bas
1685:(Sieb.) (Shikimi-no-ki in Japanese)].
1555:
1443:
1309:. Due to their role in the manufacture of
1288:
986:in 1960 for use in food, it was used as a
336:
197:
175:
2872:
2863:
1476:
293:
2848:
2822:
2271:Pharmacy and Pharmacology Communications
1292:
895:Safrole can be obtained through natural
778:in Japan). In 1844, the French chemist
2851:"Harvesting Trees to Make Ecstasy Drug"
2788:
2185:European Journal of Medicinal Chemistry
1875:
1672:
1521:
332:
3091:
2879:Perspectives on new crops and new uses
1960:
1845:
1782:
1640:
1485:
1407:
956:high-performance liquid chromatography
188:
2913:
2746:International Narcotics Control Board
2381:
2379:
2377:
2375:
2331:
2329:
2327:
1813:
1675:"Sur les principes constituants de l'
1631:(Grimaux & Ruotte, 1869), p. 929.
1258:Lawrence Berkeley National Laboratory
860:
364:Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N
155:
135:
1846:Harvey, John L. (December 2, 1960).
1679:(Sieb.) (Shikimi-no-ki en japonais)"
466:11 °C (52 °F; 284 K)
2536:Toxicology and Applied Pharmacology
1234:International Fragrance Association
374:Key: ZMQAAUBTXCXRIC-UHFFFAOYAD
248:
232:
13:
2849:Blickman, Tom (February 3, 2009).
2372:
2324:
1884:
1869:
1713:Fittig, Rud.; Remsen, Ira (1871).
1681:[On the substances composing I
1663:See structural formula on p. 1941.
1263:
888:In the US, commercially available
70:3,4-Methylenedioxyphenyl-2-propene
14:
3130:
2898:
2298:Journal of Heterocyclic Chemistry
1747:; see the structural formula for
782:(1817–1879) determined safrole's
2823:Campbell, Sam (30 August 2009).
2048:10.1034/j.1600-0765.2003.01652.x
1963:The Journal of Organic Chemistry
1562:Annales de Chimie et de Physique
786:. In 1869, the French chemists
630:
528:
523:
422:
34:
25:
2816:
2782:
2768:
2757:
2739:
2703:
2668:
2645:
2634:
2599:
2562:
2527:
2510:
2466:
2432:Chemical Research in Toxicology
2422:
2289:
2262:
2219:
2172:
2148:
2113:
2070:
2036:Journal of Periodontal Research
1997:
1954:
1911:
1897:Journal of the Chemical Society
1878:Kings Chem Guide Second Edition
1839:
1807:
1776:
1767:
1758:
1706:
1666:
1634:
1580:Grimaux, E; Ruotte, J. (1869).
1423:from the original on 2023-08-03
1301:Safrole is listed as a Table I
961:
626:(at 25 °C , 100 kPa).
66:5-(2-Propenyl)-1,3-benzodioxole
1625:
1573:
1549:
1536:
1514:
1401:
1385:
879:, and sassafras oil made from
794:. By 1884, the German chemist
604:
428:
416:
1:
2689:10.1016/S0278-6915(99)00055-1
2585:10.1016/S0278-6915(99)00055-1
2338:Food and Cosmetics Toxicology
2240:10.1016/s0960-894x(97)10216-5
2197:10.1016/s0223-5234(00)00120-3
2018:10.1016/s0021-9673(01)88300-x
1379:
1056:
1043:
2677:Food and Chemical Toxicology
2620:10.1016/0300-483X(77)90039-7
2572:Food and Chemical Toxicology
2548:10.1016/0041-008x(65)90069-4
2478:. Animal Models for Autism.
2400:10.1016/0165-1218(82)90003-9
2350:10.1016/0015-6264(81)90518-6
1582:"Sur l'essence de sassafras"
1488:Journal of Organic Chemistry
1158:allows the molecule to form
1020:
7:
2006:Journal of Chromatography A
1773:(Eijkman, 1885), pp. 41–42.
1764:(Eijkman, 1885), pp. 40–41.
1362:
1297:MDMA synthesis from safrole
1125:
1025:It can be synthesized from
809:In 1885, the Dutch chemist
10:
3135:
2877:. In Janick, Jules (ed.).
2476:Behavioural Brain Research
2283:10.1211/146080899128734370
1721:and its cleavage products
1564:. 3rd series (in French).
1332:The root bark of American
1185:which are attached to the
917:anhydrous calcium chloride
857:group was an allyl group.
757:
3119:IARC Group 2B carcinogens
2948:
2725:10.1016/j.lfs.2006.11.041
2488:10.1016/j.bbr.2006.07.025
2091:10.1016/j.vph.2005.04.004
1801:10.1002/cber.188601901243
723:, which grows in eastern
620:
504:
499:
403:
383:
348:
75:
63:
47:
42:
33:
24:
1855:Federal Register Archive
1832:10.1002/cber.18880210181
1743:10.1002/jlac.18711590202
1699:10.1002/recl.18850040202
1659:10.1002/cber.18840170278
1641:Poleck, Theodor (1884).
1419:(published 2023-04-04).
1344:Cinnamomum parthenoxylon
734:in the synthesis of the
575:Precautionary statements
2789:Ledgard, Jared (2010).
2310:10.1002/jhet.5570290652
1417:Diário Oficial da União
1289:Use in MDMA manufacture
1187:endoplasmatic reticulum
811:Johann Frederik Eijkman
483:Magnetic susceptibility
1673:Eijkman, J.F. (1885).
1522:Semmler, F.W. (1907).
1397:(11th ed.). 8287.
1298:
1275:central nervous system
1172:competitive inhibition
1119:Glutathione peroxidase
890:culinary sassafras oil
815:Wilhelm Rudolph Fittig
2079:Vascular Pharmacology
1932:10.1055/s-2006-959379
1462:10.1055/s-2006-959379
1296:
875:, a plant growing in
2430:1'-hydroxysafrole".
2134:10.1039/jr9270001663
1905:10.1039/JR9270001663
1876:Ledgard, J. (2010).
1814:Brühl, J.W. (1888).
1783:Poleck, Th. (1886).
1351:, in particular the
1252:, and herbs such as
1150:. Metabolism of the
53:5-(Prop-2-en-1-yl)-2
49:Preferred IUPAC name
3104:Perfume ingredients
1975:10.1021/jo01161a020
1677:Illicium religiosum
1556:Saint-Èvre (1844).
1500:10.1021/jo01161a020
671:with the formula CH
446: g·mol
68:5-Allylbenzodioxole
21:
2751:2008-02-27 at the
1836:; see pp. 474–477.
1731:Annalen der Chemie
1683:llicium religiosum
1353:Cardamom Mountains
1339:steam distillation
1323:European Community
1299:
1138:conversion of the
972:piperonyl butoxide
913:steam distillation
861:Natural occurrence
780:Édouard Saint-Èvre
740:piperonyl butoxide
653:Infobox references
19:
3086:
3085:
3053:Methyl isoeugenol
2888:978-0-9615027-0-6
2444:10.1021/tx040001v
2388:Mutation Research
1446:Sassafras albidum
1087:epoxide hydratase
1009:Safrole exhibits
925:Sassafras albidum
902:Sassafras albidum
882:Sassafras albidum
806:(cyclic ethers).
784:empirical formula
771:Illicium anisatum
765:Sassafras albidum
720:Sassafras albidum
713:, which grows in
661:Chemical compound
659:
658:
613:(Drug precursors)
608:
553:Hazard statements
395:C=CCc1ccc2OCOc2c1
317:CompTox Dashboard
117:Interactive image
57:-1,3-benzodioxole
16:Chemical compound
3126:
3073:Pseudoisoeugenol
2934:
2927:
2920:
2911:
2910:
2893:
2892:
2870:
2861:
2860:
2846:
2837:
2836:
2834:
2832:
2820:
2814:
2813:
2811:
2809:
2792:Kings Chem Guide
2786:
2780:
2772:
2766:
2761:
2755:
2743:
2737:
2736:
2719:(11): 999–1006.
2707:
2701:
2700:
2672:
2666:
2665:
2663:
2662:
2657:
2649:
2643:
2638:
2632:
2631:
2603:
2597:
2596:
2566:
2560:
2559:
2531:
2525:
2524:
2514:
2508:
2507:
2470:
2464:
2463:
2438:(9): 1245–1250.
2426:
2420:
2419:
2383:
2370:
2369:
2333:
2322:
2321:
2304:(6): 1667–1669.
2293:
2287:
2286:
2266:
2260:
2259:
2223:
2217:
2216:
2176:
2170:
2169:
2167:
2166:
2152:
2146:
2145:
2117:
2111:
2110:
2074:
2068:
2067:
2031:
2022:
2021:
2001:
1995:
1994:
1958:
1952:
1951:
1915:
1909:
1908:
1888:
1882:
1881:
1873:
1867:
1866:
1864:
1862:
1852:
1843:
1837:
1835:
1811:
1805:
1804:
1780:
1774:
1771:
1765:
1762:
1756:
1746:
1710:
1704:
1703:; see pp. 39–40.
1702:
1670:
1664:
1662:
1653:(2): 1940–1944.
1638:
1632:
1629:
1623:
1593:
1577:
1571:
1569:
1553:
1547:
1540:
1534:
1533:
1518:
1512:
1511:
1483:
1474:
1473:
1441:
1432:
1431:
1429:
1428:
1405:
1399:
1398:
1389:
1160:ligand complexes
1132:hepatocarcinogen
1098:propenylcatechol
1096:and its isomer,
1075:sulfotransferase
1073:reaction with a
931:Ocotea odorifera
742:, the fragrance
669:organic compound
643:
637:
634:
633:
606:
603:
590:
586:
582:
568:
564:
560:
532:
527:
495:
493:
445:
430:
424:
418:
411:Chemical formula
341:
340:
325:
323:
297:
261:
250:
236:
209:
201:
190:
179:
159:
139:
119:
95:
38:
29:
22:
18:
3134:
3133:
3129:
3128:
3127:
3125:
3124:
3123:
3114:Allyl compounds
3089:
3088:
3087:
3082:
2944:
2938:
2901:
2896:
2889:
2871:
2864:
2847:
2840:
2830:
2828:
2821:
2817:
2807:
2805:
2803:
2787:
2783:
2776:The Merck Index
2773:
2769:
2762:
2758:
2753:Wayback Machine
2744:
2740:
2708:
2704:
2673:
2669:
2660:
2658:
2655:
2651:
2650:
2646:
2639:
2635:
2604:
2600:
2567:
2563:
2532:
2528:
2515:
2511:
2471:
2467:
2427:
2423:
2384:
2373:
2334:
2325:
2294:
2290:
2277:(12): 673–678.
2267:
2263:
2224:
2220:
2177:
2173:
2164:
2162:
2154:
2153:
2149:
2118:
2114:
2075:
2071:
2032:
2025:
2002:
1998:
1959:
1955:
1916:
1912:
1889:
1885:
1874:
1870:
1860:
1858:
1850:
1844:
1840:
1812:
1808:
1781:
1777:
1772:
1768:
1763:
1759:
1711:
1707:
1671:
1667:
1639:
1635:
1630:
1626:
1621:
1617:
1613:
1607:
1603:
1599:
1578:
1574:
1554:
1550:
1541:
1537:
1519:
1515:
1484:
1477:
1442:
1435:
1426:
1424:
1406:
1402:
1391:
1390:
1386:
1382:
1365:
1327:List I chemical
1291:
1266:
1264:Adverse effects
1164:cytochrome P450
1128:
1083:safrole epoxide
1071:drug metabolism
1067:cytochrome P450
1059:
1046:
1023:
1015:anti-angiogenic
964:
908:Ocotea cymbarum
872:Ocotea pretiosa
863:
856:
852:
848:
844:
836:
828:
824:
788:Édouard Grimaux
760:
710:Ocotea pretiosa
697:phenylpropanoid
694:
690:
686:
682:
678:
674:
662:
655:
650:
649:
648: ?)
639:
635:
631:
627:
616:
577:
555:
541:
520:
491:
489:
486:
443:
433:
427:
421:
413:
399:
396:
391:
390:
379:
376:
375:
372:
366:
365:
362:
356:
355:
344:
326:
319:
300:
280:
264:
251:
239:
219:
182:
162:
142:
122:
109:
98:
85:
71:
69:
67:
59:
58:
17:
12:
11:
5:
3132:
3122:
3121:
3116:
3111:
3106:
3101:
3099:Phenylpropenes
3084:
3083:
3081:
3080:
3075:
3070:
3065:
3060:
3055:
3050:
3048:Methyl eugenol
3045:
3040:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2954:
2952:
2950:Phenylpropenes
2946:
2945:
2942:phenylpropenes
2937:
2936:
2929:
2922:
2914:
2908:
2907:
2900:
2899:External links
2897:
2895:
2894:
2887:
2862:
2838:
2815:
2801:
2781:
2767:
2756:
2738:
2702:
2683:(7): 697–702.
2667:
2644:
2633:
2598:
2579:(7): 697–702.
2561:
2526:
2509:
2482:(1): 149–169.
2465:
2421:
2394:(2): 127–140.
2371:
2344:(5): 657–666.
2323:
2288:
2261:
2234:(2): 183–188.
2218:
2191:(2): 187–203.
2171:
2147:
2112:
2069:
2042:(2): 130–134.
2023:
1996:
1969:(3): 443–446.
1953:
1926:(6): 574–575.
1910:
1883:
1868:
1838:
1806:
1775:
1766:
1757:
1749:Piperonylsäure
1737:(2): 129–158.
1705:
1665:
1633:
1624:
1619:
1615:
1611:
1605:
1601:
1597:
1594:From p. 928:
1586:Comptes Rendus
1572:
1548:
1535:
1513:
1475:
1433:
1411:(2023-03-31).
1400:
1383:
1381:
1378:
1377:
1376:
1371:
1364:
1361:
1349:Southeast Asia
1290:
1287:
1265:
1262:
1152:methylenedioxy
1127:
1124:
1107:propionic acid
1058:
1055:
1045:
1042:
1022:
1019:
963:
960:
869:oil made from
862:
859:
854:
850:
846:
842:
834:
831:propenyl group
826:
822:
796:Theodor Poleck
759:
756:
692:
688:
684:
680:
676:
672:
660:
657:
656:
651:
629:
628:
624:standard state
621:
618:
617:
615:
614:
600:
598:
592:
591:
578:
573:
570:
569:
556:
551:
548:
547:
542:
537:
534:
533:
521:
516:
513:
512:
502:
501:
497:
496:
494:10 cm/mol
487:
481:
478:
477:
474:
468:
467:
464:
458:
457:
454:
448:
447:
441:
435:
434:
431:
425:
419:
414:
409:
406:
405:
401:
400:
398:
397:
394:
386:
385:
384:
381:
380:
378:
377:
373:
370:
369:
367:
363:
360:
359:
351:
350:
349:
346:
345:
343:
342:
329:
327:
315:
312:
311:
308:
302:
301:
299:
298:
290:
288:
282:
281:
279:
278:
274:
272:
266:
265:
263:
262:
254:
252:
244:
241:
240:
238:
237:
229:
227:
221:
220:
218:
217:
213:
211:
203:
202:
192:
184:
183:
181:
180:
172:
170:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
124:
123:
121:
120:
112:
110:
103:
100:
99:
97:
96:
88:
86:
81:
78:
77:
73:
72:
65:
61:
60:
52:
51:
45:
44:
40:
39:
31:
30:
15:
9:
6:
4:
3:
2:
3131:
3120:
3117:
3115:
3112:
3110:
3109:Benzodioxoles
3107:
3105:
3102:
3100:
3097:
3096:
3094:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3038:Isomyristicin
3036:
3034:
3031:
3029:
3028:Isodillapiole
3026:
3024:
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2955:
2953:
2951:
2947:
2943:
2935:
2930:
2928:
2923:
2921:
2916:
2915:
2912:
2906:
2903:
2902:
2890:
2884:
2880:
2876:
2869:
2867:
2858:
2857:
2856:The Irrawaddy
2852:
2845:
2843:
2826:
2819:
2804:
2802:9780578058658
2798:
2794:
2793:
2785:
2778:
2777:
2771:
2765:
2760:
2754:
2750:
2747:
2742:
2734:
2730:
2726:
2722:
2718:
2714:
2713:Life Sciences
2706:
2698:
2694:
2690:
2686:
2682:
2678:
2671:
2654:
2648:
2642:
2637:
2629:
2625:
2621:
2617:
2613:
2609:
2602:
2594:
2590:
2586:
2582:
2578:
2574:
2573:
2565:
2557:
2553:
2549:
2545:
2541:
2537:
2530:
2522:
2521:
2513:
2505:
2501:
2497:
2493:
2489:
2485:
2481:
2477:
2469:
2461:
2457:
2453:
2449:
2445:
2441:
2437:
2433:
2425:
2417:
2413:
2409:
2405:
2401:
2397:
2393:
2389:
2382:
2380:
2378:
2376:
2367:
2363:
2359:
2355:
2351:
2347:
2343:
2339:
2332:
2330:
2328:
2319:
2315:
2311:
2307:
2303:
2299:
2292:
2284:
2280:
2276:
2272:
2265:
2257:
2253:
2249:
2245:
2241:
2237:
2233:
2229:
2222:
2214:
2210:
2206:
2202:
2198:
2194:
2190:
2186:
2182:
2175:
2161:
2157:
2151:
2143:
2139:
2135:
2131:
2128:: 1663–1666.
2127:
2126:J. Chem. Soc.
2123:
2116:
2108:
2104:
2100:
2096:
2092:
2088:
2084:
2080:
2073:
2065:
2061:
2057:
2053:
2049:
2045:
2041:
2037:
2030:
2028:
2019:
2015:
2011:
2007:
2000:
1992:
1988:
1984:
1980:
1976:
1972:
1968:
1964:
1957:
1949:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1920:Planta Medica
1914:
1906:
1902:
1899:: 1663–1666.
1898:
1894:
1887:
1879:
1872:
1856:
1849:
1842:
1833:
1829:
1825:
1822:(in German).
1821:
1817:
1810:
1802:
1798:
1795:: 1094–1098.
1794:
1791:(in German).
1790:
1786:
1779:
1770:
1761:
1754:
1750:
1744:
1740:
1736:
1733:(in German).
1732:
1728:
1724:
1720:
1716:
1709:
1700:
1696:
1692:
1689:(in French).
1688:
1684:
1680:
1678:
1669:
1660:
1656:
1652:
1648:
1644:
1637:
1628:
1609:
1591:
1588:(in French).
1587:
1583:
1576:
1570:; see p. 108.
1567:
1563:
1559:
1552:
1545:
1539:
1531:
1527:
1526:
1517:
1509:
1505:
1501:
1497:
1493:
1489:
1482:
1480:
1471:
1467:
1463:
1459:
1455:
1451:
1450:Planta Medica
1447:
1440:
1438:
1422:
1418:
1414:
1410:
1404:
1396:
1395:
1388:
1384:
1375:
1372:
1370:
1367:
1366:
1360:
1358:
1354:
1350:
1346:
1345:
1340:
1335:
1330:
1328:
1324:
1320:
1316:
1312:
1308:
1304:
1295:
1286:
1284:
1280:
1276:
1271:
1261:
1259:
1255:
1251:
1247:
1243:
1237:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1210:United States
1206:
1204:
1200:
1196:
1192:
1188:
1184:
1179:
1177:
1173:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1133:
1123:
1120:
1116:
1114:
1108:
1103:
1099:
1095:
1094:allylcatechol
1090:
1088:
1084:
1080:
1076:
1072:
1068:
1064:
1054:
1052:
1041:
1039:
1034:
1032:
1031:allyl bromide
1028:
1018:
1016:
1012:
1007:
1005:
1001:
997:
993:
989:
985:
981:
977:
973:
969:
959:
957:
953:
949:
945:
941:
937:
933:
932:
927:
926:
920:
918:
914:
910:
909:
904:
903:
898:
893:
891:
886:
884:
883:
878:
874:
873:
868:
858:
840:
832:
820:
816:
812:
807:
805:
801:
797:
793:
789:
785:
781:
777:
773:
772:
767:
766:
755:
753:
749:
745:
741:
737:
733:
728:
726:
725:North America
722:
721:
716:
712:
711:
706:
702:
698:
670:
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1809:
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1778:
1769:
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1748:
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1730:
1723:piperic acid
1708:
1693:(2): 32–54.
1690:
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1494:(3): 443–6.
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1456:(6): 574–5.
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1445:
1425:. Retrieved
1403:
1392:
1387:
1342:
1331:
1300:
1267:
1250:black pepper
1238:
1222:carcinogenic
1207:
1191:mutagenicity
1180:
1129:
1115:-transferase
1112:
1111:glutathione
1091:
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962:Applications
952:black pepper
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829:group was a
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664:
663:
596:Legal status
544:
506:
270:RTECS number
157:ChEMBL242273
76:Identifiers
64:Other names
54:
3068:Osmorhizole
3063:Nothoapiole
2831:2 September
2808:6 September
2520:Irish Times
2124:-safrole".
2012:: 455–461.
1895:-safrole".
1826:: 457–477.
1394:Merck Index
1313:, safrole,
1283:nerve cells
1270:neutrophils
1199:liver cells
1154:group to a
1140:allyl group
1079:DNA adducts
1017:functions.
996:chewing gum
988:food flavor
968:insecticide
936:camphor oil
839:allyl group
833:(R−CH=CH−CH
792:allyl group
736:insecticide
705:antifeedant
539:Signal word
456:1.096 g/cm
404:Properties
195:100.002.133
3093:Categories
3058:Myristicin
3043:Isosafrole
3033:Isoeugenol
3018:Exalatacin
2998:Dillapiole
2983:Chavibetol
2661:2013-10-22
2608:Toxicology
2165:2017-04-27
2160:erowid.org
1727:piperidine
1592:: 928–930.
1568:: 107–113.
1427:2023-08-15
1380:References
1315:isosafrole
1305:under the
1203:cell death
1178:activity.
1057:Metabolism
1044:Isosafrole
1011:antibiotic
1000:toothpaste
897:extraction
819:Ira Remsen
748:isosafrole
738:synergist
518:Pictograms
439:Molar mass
295:RSB34337V9
168:ChemSpider
137:CHEBI:8994
104:3D model (
83:CAS Number
3023:Isoapiole
3008:Estragole
2993:Croweacin
2940:Types of
2452:0893-228X
2408:0027-5107
2358:0015-6264
2318:1943-5193
2248:0960-894X
2205:0223-5234
2142:0368-1769
2099:1537-1891
2056:0022-3484
1983:0022-3263
1940:0032-0943
1374:Root beer
1369:Sassafras
1334:sassafras
1319:piperonal
1303:precursor
1279:apoptosis
1214:root beer
1183:ribosomes
1136:Metabolic
1021:Synthesis
992:root beer
774:, called
744:piperonal
732:precursor
701:sassafras
589:P308+P313
509:labelling
306:UN number
277:CY2800000
216:202-345-4
208:EC Number
3003:Elemicin
2988:Chavicol
2978:Carpacin
2968:Asaricin
2958:Anethole
2749:Archived
2733:17188719
2697:10496370
2593:10496370
2556:14259070
2496:16950524
2460:15377158
2213:10758281
2107:15936989
2064:12608906
1991:18863852
1719:piperine
1508:18863852
1421:Archived
1363:See also
1357:Cambodia
1347:tree in
1242:cinnamon
1230:perfumes
1148:proteins
1126:Toxicity
1027:catechol
948:cinnamon
837:) or an
804:epoxides
730:It is a
611:Class D1
500:Hazards
485:(χ)
177:13848731
20:Safrole
3078:Safrole
3013:Eugenol
2973:Asarone
2504:3054752
2416:6808388
2366:7030889
2256:9871651
1948:8824955
1729:].
1470:8824955
1281:of the
1232:by the
1208:In the
1176:oxidase
1156:carbene
1102:Eugenol
976:ecstasy
867:camphor
800:benzene
776:shikimi
758:History
665:Safrole
646:what is
644: (
452:Density
444:162.188
246:PubChem
93:94-59-7
2963:Apiole
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1317:, and
1248:, and
1246:nutmeg
1195:tumors
984:US FDA
950:, and
944:nutmeg
877:Brazil
845:−CH=CH
717:, and
715:Brazil
667:is an
641:verify
638:
609:
545:Danger
388:SMILES
234:C10490
148:ChEMBL
43:Names
2656:(PDF)
2628:14422
2500:S2CID
1851:(PDF)
1528:[
1254:basil
1162:with
1063:allyl
1004:soaps
940:anise
899:from
841:(R−CH
691:CH=CH
490:−97.5
353:InChI
310:3082
128:ChEBI
106:JSmol
2883:ISBN
2833:2009
2810:2014
2797:ISBN
2729:PMID
2693:PMID
2624:PMID
2589:PMID
2552:PMID
2492:PMID
2456:PMID
2448:ISSN
2412:PMID
2404:ISSN
2362:PMID
2354:ISSN
2314:ISSN
2252:PMID
2244:ISSN
2209:PMID
2201:ISSN
2138:ISSN
2103:PMID
2095:ISSN
2060:PMID
2052:ISSN
1987:PMID
1979:ISSN
1944:PMID
1936:ISSN
1863:2022
1725:and
1504:PMID
1466:PMID
1311:MDMA
1228:and
1226:soap
1201:and
1168:P448
1166:and
1146:and
1051:MDMA
1013:and
980:MDMA
905:and
752:MDMA
746:via
585:P281
581:P201
567:H350
563:H341
559:H302
286:UNII
259:5144
225:KEGG
2721:doi
2685:doi
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2480:176
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