欖香素

欖香素
臨床資料
給藥途徑	經口
法律規範狀態
法律規範	未受管制;
識別資訊
	IUPAC命名法 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene; ;
CAS號	487-11-6
PubChem CID	10248;
ChemSpider	9830 ;
UNII	HSZ191AKAN;
KEGG	C10451 ;
ChEMBL	ChEMBL458690 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID60197586 ;
ECHA InfoCard	100.006.954
化學資訊
化學式	C12H16O3
摩爾質量	208.26 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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 ;

欖香素（又稱欖香脂素）是一種苯丙烯，是多種植物精油的組分之一。^[1]^[2]

天然來源

欖香素是存在於油樹脂（英語：oleoresin）中，也是呂宋橄欖（英語：Canarium luzonicum）精油的成分之一；欖香素的英文名稱 elemicin 即源自這種樹（elemi）。有研究顯示，新鮮的呂宋橄欖精油中含有2.4%的欖香素。^[1]肉豆蔻的油和干皮中也含有欖香素，分別占比2.4%和10.5%。^[2]從結構上來看，欖香素和肉豆蔻醚十分相似，兩種物質也都見於肉豆蔻中。

分離

欖香素最早是通過真空蒸餾，從呂宋橄欖精油中分離出來的。蒸餾溫度在162-165 °C之間，氣壓減至10托。^[3]^[4]

製備

欖香素可以通過丁香酚和烯丙基溴，發生威廉姆遜合成反應和克萊森重排反應製得。^[5]^[6]次要發生的科普重排反應使得對位能進行親電芳香取代。^[7]這種情況下的產量能達到85%以上。^[8]

用途

欖香素可用於合成麥司卡林。^[9]

藥理學

生肉豆蔻能起到類似抗膽鹼劑的反應，其主要作用就源於欖香素和肉豆蔻醚。^[10]^[11]

參見

參考資料

^ ^1.0 ^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.
^ ^2.0 ^2.1 Leela N. Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. 2008: 165–188 [170] [2021-04-11]. ISBN 9781845934057. （原始內容存檔於2021-04-11）.
^ 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. （原始內容存檔於2021-04-11）.
^ 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. （原始內容存檔於2021-04-11）.
^ 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. （原始內容存檔於2021-04-11）.
^ Synthesis of Elemicin and of isoElemicin. Journal of the Chemical Society, Abstracts. 1918, 114: i428. doi:10.1039/CA9181400421.
^ Thomas, Laue. Named Organic Reactions, 2nd Edition. Wolfsburg, Germany: John Wiley & Sons, Ltd. 2005: 58–60 [59] [2021-04-11]. ISBN 978-0470010402. （原始內容存檔於2021-04-11）.
^ 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. （原始內容存檔 (PDF)於2021-05-10）.
^ 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.
^ 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.
^ 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. （原始內容 (pdf)存檔於2014-04-20）.

[Baser-1] 1.0 ^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] 2.0 ^2.1 Leela N. Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. 2008: 165–188 [170] [2021-04-11]. ISBN 9781845934057. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔 (PDF)於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.

[pmid15249817-10] 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. （原始內容 (pdf)存檔於2014-04-20）.

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