丁香油酚

丁香油酚
	IUPAC名; 4-烯丙基-2-甲氧基苯酚
英文名	Eugenol
别名	甲氧基-4-(2-丙烯基)苯酚; 2-甲氧基-4-丙烯基苯基苯乙醚; 丁香油酚; 丁子香酚; 丁子香酸; 烯丙基甲氧基苯酚; 异丁香酚苯乙醚
识别
CAS号	97-53-0
PubChem	12636
ChemSpider	13876103
SMILES	Oc1ccc(cc1OC)CC=C;
InChI	1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3;
InChIKey	RRAFCDWBNXTKKO-UHFFFAOYAJ
ChEBI	4917
KEGG	D04117
性质
化学式	C10H12O2
摩尔质量	164.20 g·mol⁻¹
密度	1.06 g/cm3
熔点	−9 °C（264 K）
沸点	256 °C（529 K）
危险性
	欧盟危险性符号; 有害 Xn
警示术语	R：R22, R36/37/38, R38, R40, R42/43
安全术语	S：S23, S24/25, S26, S36
闪点	104℃
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

丁香油酚（英语：Eugenol，分子式C₁₀H₁₂O₂），是一种有机化合物，存在于多种植物中，富含于其精油中，如月桂油等^[1]^[2]。具有持久香气，常作为香皂的香料。

丁香油酚是苯基丙烯，烯丙基链取代的邻甲氧基苯酚。丁香油酚是苯丙类化合物中的一员。它是一种无色至淡黄色油状液体，从特别是在丁香油、肉豆蔻、肉桂、罗勒和月桂叶某些精油提取。它存在于丁香花蕾油中80-90％的浓度，在丁香叶油82-88％的浓度。

丁香油酚的英文名字“eugenol”源自丁香其中一个属名——“Eugenia”（番樱桃属）。丁香的香气主要来自其中的丁香油酚。

性质

物理性质

无色至淡黄色微稠厚液体，具强烈丁香气味^[1]。
溶于乙醇、乙醚、氯仿和精油，不溶于水。^[3]

化学性质

不稳定、抗氧化^[4]
长期暴露空气中会变黑变稠黏，出现刺激性臭味。

制备

将天然精油碱处理单离生成。
可由愈创木酚和烯丙基氯（或烯丙醇）反应，经烯丙基化生成^[1]。

用途

抗菌、局部麻醉药和降血压。^[4]如鱼贩给鱼洒“丁香油水门汀”作为水产麻醉剂及鱼类麻醉剂。^[5]^[6]^[7]
制造香水、香精、精油、修饰剂和定香剂。

危害

过量摄取会出现心悸、头晕、呕吐、腹泻、昏迷及抽搐等症状，可引起皮炎及皮肤过敏^[8]。1993年，曾报道一名2岁男童服用5至10毫升丁香油酚后险些丧命。^[9]
具有肝毒性，影响肝功能。^[10]^[11]

含有丁香油酚的植物

参见

参考文献

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 （中文）ChemicalBook 丁香油酚（页面存档备份，存于互联网档案馆）
^ Peter William Atkins. 第4章　味覺、嗅覺和痛覺. 化學分子世界導覽一. 天下文化. 2010: 211. ISBN 978-986-216-220-0.
^ 化工词典丁香油酚. [2011-05-20]. （原始内容存档于2011-10-24）.
^ ^4.0 ^4.1 （中文）丁香油酚的药理作用（页面存档备份，存于互联网档案馆）
^ 「麻醉魚」是怎麼回事？ | 科學人 | 果殼網科技有意思. [2014-08-15]. （原始内容存档于2015-04-15）.
^ 丁香油麻醉魚？魚市場保全：行之有年. [2014-08-15]. （原始内容存档于2014-08-15）.
^ 北京最大海鲜市场用麻醉药喂鱼商人称为卖相好. [2014-08-15]. （原始内容存档于2016-02-23）.
^ Eugenol Oil Overdose （页面存档备份，存于互联网档案馆）, New York Times Health Guide
^ Hartnoll, G; Moore, D; Douek, D. Near fatal ingestion of oil of cloves.. Archives of disease in childhood. 1993, 69 (3): 392–3. PMC 1029532 . PMID 8215554. doi:10.1136/adc.69.3.392.
^ Thompson, DC; Barhoumi, R; Burghardt, RC. Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays.. Toxicology and applied pharmacology. 1998, 149 (1): 55–63. PMID 9512727. doi:10.1006/taap.1997.8348.
^ Fujisawa, S; Atsumi, T; Kadoma, Y; Sakagami, H. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity.. Toxicology. 2002, 177 (1): 39–54. PMID 12126794. doi:10.1016/S0300-483X(02)00194-4.
^ Pathak, S. B.; Niranjan, K.; Padh, H.; Rajani, M.; et al. TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove. Chromatographia. 2004, 60 (3 - 4): 241–244. doi:10.1365/s10337-004-0373-y.
^ ^13.0 ^13.1 BULLERMAN, L. B.; Lieu, F. Y.; Seier, Sally A.; et al. INHIBITION OF GROWTH AND AFLATOXIN PRODUCTION BY CINNAMON AND CLOVE OILS. CINNAMIC ALDEHYDE AND EUGENOL. Journal of Food Science. 1977, 42 (4): 1107–1109. doi:10.1111/j.1365-2621.1977.tb12677.x.
^ Lee, Kwang-Geun; Takayuki Shibamoto. Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry]. Food Chemistry. 2001, 74 (4): 443–448 [3 July 2009]. doi:10.1016/S0308-8146(01)00161-3.
^ Kreydiyyeh, S. I.; Usta, J; Copti, R; et al. Effect of cinnamon, clove and some of their constituents on the Na⁺-K⁺-ATPase activity and alanine absorption in the rat jejunum. Food and Chemical Toxicology. 2000, 38 (9): 755–762 [3 July 2009]. PMID 10930696. doi:10.1016/S0278-6915(00)00073-9.
^ Dighe, V. V.; Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H.; et al. Quantitative Determination of Eugenol from Cinnamomum tamala Nees and Eberm. Leaf Powder and Polyherbal Formulation Using Reverse Phase Liquid Chromatography. Chromatographia. 2005, 61 (9 - 10): 443–446. doi:10.1365/s10337-005-0527-6.
^ Bennett, A.; Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V.; Di Carlo, G.; et al. The biological activity of eugenol, a major constituent of nutmeg (Myristica fragrans): Studies on prostaglandins, the intestine and other tissues. Phytotherapy Research. 1988, 2 (3): 124–130. doi:10.1002/ptr.2650020305.
^ Johnson, C. B.; Kirby, J.; Naxakis, G.; Pearson, S. Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.). Phytochemistry. 1999, 51 (4): 507–510 [24 November 2009]. doi:10.1016/S0031-9422(98)00767-5.
^ Celso Vataru Nakamura, Tania Ueda-Nakamura, Erika Bando, Abrahão Fernandes Negrão Melo, Díogenes Aparício Garcia Cortez, Benedito Prado Dias Filho, "Antibacterial Activity of Ocimum gratissimum L. Essential Oil", Memórias do Instituto Oswaldo Cruz, Vol. 94(5): 675-678.. [2011-05-18]. （原始内容存档于2012-10-09）.
^ Lemon balm. University of Maryland Medical Center. [2010-12-07]. （原始内容存档于2013-05-22）.

外部链接

（英文）Kegley, S.E., Hill, B.R., Orme S., Choi A.H., Toxicity Information for Eugenol（页面存档备份，存于互联网档案馆） in PAN Pesticide Database, Pesticide Action Network, North America (San Francisco, CA, 2010)
（英文）Eugenol (Mmm, dentist) : Molecule of the Day. ScienceBlogs. 2006-10-04 [2010-12-07]. （原始内容存档于2009-12-30）. (Eugenol entry on the Molecule of the Day blog)
丁子香酚 Eugenol （页面存档备份，存于互联网档案馆）中草药化学图像数据库 (香港浸会大学中医药学院) （中文）（英文）

[ChemicalBook-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 （中文）ChemicalBook 丁香油酚（页面存档备份，存于互联网档案馆）

[化學分子世界導覽一-2] Peter William Atkins. 第4章　味覺、嗅覺和痛覺. 化學分子世界導覽一. 天下文化. 2010: 211. ISBN 978-986-216-220-0.

[3] 化工词典丁香油酚. [2011-05-20]. （原始内容存档于2011-10-24）.

[Ref001-4] 4.0 ^4.1 （中文）丁香油酚的药理作用（页面存档备份，存于互联网档案馆）

[5] 「麻醉魚」是怎麼回事？ | 科學人 | 果殼網科技有意思. [2014-08-15]. （原始内容存档于2015-04-15）.

[6] 丁香油麻醉魚？魚市場保全：行之有年. [2014-08-15]. （原始内容存档于2014-08-15）.

[7] 北京最大海鲜市场用麻醉药喂鱼商人称为卖相好. [2014-08-15]. （原始内容存档于2016-02-23）.

[8] Eugenol Oil Overdose （页面存档备份，存于互联网档案馆）, New York Times Health Guide

[9] Hartnoll, G; Moore, D; Douek, D. Near fatal ingestion of oil of cloves.. Archives of disease in childhood. 1993, 69 (3): 392–3. PMC 1029532 . PMID 8215554. doi:10.1136/adc.69.3.392.

[10] Thompson, DC; Barhoumi, R; Burghardt, RC. Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays.. Toxicology and applied pharmacology. 1998, 149 (1): 55–63. PMID 9512727. doi:10.1006/taap.1997.8348.

[11] Fujisawa, S; Atsumi, T; Kadoma, Y; Sakagami, H. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity.. Toxicology. 2002, 177 (1): 39–54. PMID 12126794. doi:10.1016/S0300-483X(02)00194-4.

[tdmq-12] Pathak, S. B.; Niranjan, K.; Padh, H.; Rajani, M.; et al. TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove. Chromatographia. 2004, 60 (3 - 4): 241–244. doi:10.1365/s10337-004-0373-y.

[igap-13] 13.0 ^13.1 BULLERMAN, L. B.; Lieu, F. Y.; Seier, Sally A.; et al. INHIBITION OF GROWTH AND AFLATOXIN PRODUCTION BY CINNAMON AND CLOVE OILS. CINNAMIC ALDEHYDE AND EUGENOL. Journal of Food Science. 1977, 42 (4): 1107–1109. doi:10.1111/j.1365-2621.1977.tb12677.x.

[apae-14] Lee, Kwang-Geun; Takayuki Shibamoto. Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry]. Food Chemistry. 2001, 74 (4): 443–448 [3 July 2009]. doi:10.1016/S0308-8146(01)00161-3.

[eccs-15] Kreydiyyeh, S. I.; Usta, J; Copti, R; et al. Effect of cinnamon, clove and some of their constituents on the Na⁺-K⁺-ATPase activity and alanine absorption in the rat jejunum. Food and Chemical Toxicology. 2000, 38 (9): 755–762 [3 July 2009]. PMID 10930696. doi:10.1016/S0278-6915(00)00073-9.

[qdec-16] Dighe, V. V.; Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H.; et al. Quantitative Determination of Eugenol from Cinnamomum tamala Nees and Eberm. Leaf Powder and Polyherbal Formulation Using Reverse Phase Liquid Chromatography. Chromatographia. 2005, 61 (9 - 10): 443–446. doi:10.1365/s10337-005-0527-6.

[baem-17] Bennett, A.; Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V.; Di Carlo, G.; et al. The biological activity of eugenol, a major constituent of nutmeg (Myristica fragrans): Studies on prostaglandins, the intestine and other tissues. Phytotherapy Research. 1988, 2 (3): 124–130. doi:10.1002/ptr.2650020305.

[osc-18] Johnson, C. B.; Kirby, J.; Naxakis, G.; Pearson, S. Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.). Phytochemistry. 1999, 51 (4): 507–510 [24 November 2009]. doi:10.1016/S0031-9422(98)00767-5.

[19] Celso Vataru Nakamura, Tania Ueda-Nakamura, Erika Bando, Abrahão Fernandes Negrão Melo, Díogenes Aparício Garcia Cortez, Benedito Prado Dias Filho, "Antibacterial Activity of Ocimum gratissimum L. Essential Oil", Memórias do Instituto Oswaldo Cruz, Vol. 94(5): 675-678.. [2011-05-18]. （原始内容存档于2012-10-09）.

[20] Lemon balm. University of Maryland Medical Center. [2010-12-07]. （原始内容存档于2013-05-22）.

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