榄香素

榄香素
临床资料
给药途径	经口
法律规范状态
法律规范	未受管制;
识别信息
	IUPAC命名法 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene; ;
CAS号	487-11-6
PubChem CID	10248;
ChemSpider	9830 ;
UNII	HSZ191AKAN;
KEGG	C10451 ;
ChEMBL	ChEMBL458690 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID60197586 ;
ECHA InfoCard	100.006.954
化学信息
化学式	C12H16O3
摩尔质量	208.26 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES C=CCC1=CC(OC)=C(OC)C(OC)=C1;
	InChI InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 ; Key:BPLQKQKXWHCZSS-UHFFFAOYSA-N ;

榄香素（又称榄香脂素）是一种苯丙烯，是多种植物精油的组分之一。^[1]^[2]

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榄香素是存在于油树脂（英语：oleoresin）中，也是吕宋橄榄（英语：Canarium luzonicum）精油的成分之一；榄香素的英文名称 elemicin 即源自这种树（elemi）。有研究显示，新鲜的吕宋橄榄精油中含有2.4%的榄香素。^[1]肉豆蔻的油和干皮中也含有榄香素，分别占比2.4%和10.5%。^[2]从结构上来看，榄香素和肉豆蔻醚十分相似，两种物质也都见于肉豆蔻中。

榄香素最早是通过真空蒸馏，从吕宋橄榄精油中分离出来的。蒸馏温度在162-165 °C之间，气压减至10托。^[3]^[4]

榄香素可以通过丁香酚和烯丙基溴，发生威廉姆逊合成反应和克莱森重排反应制得。^[5]^[6]次要发生的科普重排反应使得对位能进行亲电芳香取代。^[7]这种情况下的产量能达到85%以上。^[8]

榄香素可用于合成麦司卡林。^[9]

生肉豆蔻能起到类似抗胆碱剂的反应，其主要作用就源于榄香素和肉豆蔻醚。^[10]^[11]

肉豆蔻油（英语：Nutmeg oil）
肉豆蔻醚
苯丙素类（英语：Phenylpropanoid）

[1]
Villanueva MA, Torres RC, Baser KH, Özek T, Kürkçüoglu M. The Composition of Manila Elemi Oil. Flavour and Fragrance Journal. 1993, 8: 35–37. doi:10.1002/ffj.2730080107.
[2]
Leela N. Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. 2008: 165–188 [170] [2021-04-11]. ISBN 9781845934057. （原始内容存档于2021-04-11）.
[3]
Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen. Journal of the Chemical Society, Abstracts. 1908, 94 (A493): 557–558 [2021-04-11]. doi:10.1039/CA9089400493. （原始内容存档于2021-04-11）.
[4]
Semmler, Friedrich. Zur Kenntnis der Bestandteile der ätherischen Öle. (Über das Elemicin, einen hochsiedenden Bestandteil des Elemiöls, und über Ersetzung von Alkyloxy-gruppen am Benzolkern durch Wasserstoff.). Berichte der Deutschen Chemischen Gesellschaft. 1908, 41 (2): 1768–1775 [2021-04-11]. doi:10.1002/cber.19080410240. （原始内容存档于2021-04-11）.
[5]
Mauthner F. Die Synthese des Elemicins und Isoelemicins. Justus Liebigs Annalen der Chemie. 1918, 414 (2): 250–255 [2021-04-11]. doi:10.1002/jlac.19184140213. （原始内容存档于2021-04-11）.
[6]
Synthesis of Elemicin and of isoElemicin. Journal of the Chemical Society, Abstracts. 1918, 114: i428. doi:10.1039/CA9181400421.
[7]
Thomas, Laue. Named Organic Reactions, 2nd Edition. Wolfsburg, Germany: John Wiley & Sons, Ltd. 2005: 58–60 [59] [2021-04-11]. ISBN 978-0470010402. （原始内容存档于2021-04-11）.
[8]
Adams, Rodger. The Claisen Rearrangement (PDF). Organic Reactions, Volume II. New York: John Wiley & Sons, Inc. 1944: 2–44 [44] [2021-04-11]. ISBN 978-0471264187. doi:10.1002/0471264180.or002.01. （原始内容存档 (PDF)于2021-05-10）.
[9]
Hahn, Georg; Wassmuth, Heinrich. Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins. Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 1934, 67 (4): 696–708. doi:10.1002/cber.19340670430.
[10]
McKenna A, Nordt SP, Ryan J. Acute nutmeg poisoning. European Journal of Emergency Medicine. August 2004, 11 (4): 240–1. PMID 15249817. doi:10.1097/01.mej.0000127649.69328.a5.
[11]
Shulgin AT, Sargent T, Naranjo C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. Psychopharmacology Bulletin. December 1967, 4 (3): 13 [2015-09-02]. PMID 5615546. （原始内容 (pdf)存档于2014-04-20）.

[Baser-1] [1]
Villanueva MA, Torres RC, Baser KH, Özek T, Kürkçüoglu M. The Composition of Manila Elemi Oil. Flavour and Fragrance Journal. 1993, 8: 35–37. doi:10.1002/ffj.2730080107.

[ChemOfSpices-2] [2]
Leela N. Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. 2008: 165–188 [170] [2021-04-11]. ISBN 9781845934057. （原始内容存档于2021-04-11）.

[3] [3]
Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen. Journal of the Chemical Society, Abstracts. 1908, 94 (A493): 557–558 [2021-04-11]. doi:10.1039/CA9089400493. （原始内容存档于2021-04-11）.

[4] [4]
Semmler, Friedrich. Zur Kenntnis der Bestandteile der ätherischen Öle. (Über das Elemicin, einen hochsiedenden Bestandteil des Elemiöls, und über Ersetzung von Alkyloxy-gruppen am Benzolkern durch Wasserstoff.). Berichte der Deutschen Chemischen Gesellschaft. 1908, 41 (2): 1768–1775 [2021-04-11]. doi:10.1002/cber.19080410240. （原始内容存档于2021-04-11）.

[5] [5]
Mauthner F. Die Synthese des Elemicins und Isoelemicins. Justus Liebigs Annalen der Chemie. 1918, 414 (2): 250–255 [2021-04-11]. doi:10.1002/jlac.19184140213. （原始内容存档于2021-04-11）.

[6] [6]
Synthesis of Elemicin and of isoElemicin. Journal of the Chemical Society, Abstracts. 1918, 114: i428. doi:10.1039/CA9181400421.

[7] [7]
Thomas, Laue. Named Organic Reactions, 2nd Edition. Wolfsburg, Germany: John Wiley & Sons, Ltd. 2005: 58–60 [59] [2021-04-11]. ISBN 978-0470010402. （原始内容存档于2021-04-11）.

[8] [8]
Adams, Rodger. The Claisen Rearrangement (PDF). Organic Reactions, Volume II. New York: John Wiley & Sons, Inc. 1944: 2–44 [44] [2021-04-11]. ISBN 978-0471264187. doi:10.1002/0471264180.or002.01. （原始内容存档 (PDF)于2021-05-10）.

[9] [9]
Hahn, Georg; Wassmuth, Heinrich. Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins. Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 1934, 67 (4): 696–708. doi:10.1002/cber.19340670430.

[pmid15249817-10] [10]
McKenna A, Nordt SP, Ryan J. Acute nutmeg poisoning. European Journal of Emergency Medicine. August 2004, 11 (4): 240–1. PMID 15249817. doi:10.1097/01.mej.0000127649.69328.a5.

[11] [11]
Shulgin AT, Sargent T, Naranjo C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. Psychopharmacology Bulletin. December 1967, 4 (3): 13 [2015-09-02]. PMID 5615546. （原始内容 (pdf)存档于2014-04-20）.

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榄香素

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