PROFILPELAJAR.COM

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（英語：Eugenol，分子式C₁₀H₁₂O₂），是一種有機化合物，存在於多種植物中，富含于其精油中，如月桂油等^[1]^[2]。具有持久香氣，常作为香皂的香料。

丁香油酚是苯基丙烯，烯丙基鏈取代的鄰甲氧基苯酚。丁香油酚是苯丙類化合物中的一員。它是一種無色至淡黃色油狀液體，從特別是在丁香油、肉荳蔻、肉桂、羅勒和月桂葉某些精油提取。它存在於丁香花蕾油中80-90％的濃度，在丁香葉油82-88％的濃度。

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）。丁香的香氣主要來自其中的丁香油酚。

性質

物理性質

無色至淡黃色微稠厚液體，具強烈丁香氣味^[1]。
溶於乙醇、乙醚、氯仿和精油，不溶於水。^[3]

化學性質

不穩定、抗氧化^[4]
長期暴露空氣中会變黑變稠黏，出现刺激性臭味。

製備

將天然精油鹼處理單離生成。
可由愈創木酚和烯丙基氯（或烯丙醇）反應，經烯丙基化生成^[1]。

用途

抗菌、局部麻醉藥和降血壓。^[4]如魚販給魚灑「丁香油水門汀」作為水產麻醉劑及魚類麻醉劑。^[5]^[6]^[7]
製造香水、香精、精油、修飾劑和定香劑。

危害

過量攝取會出现心悸、頭暈、嘔吐、腹瀉、昏迷及抽搐等症状，可引起皮炎及皮膚過敏^[8]。1993年，曾报道一名2岁男童服用5至10毫升丁香油酚後险些喪命。^[9]
具有肝毒性，影響肝功能。^[10]^[11]

含有丁香油酚的植物

參見

參考文獻

^ ^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）.

外部連結

（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）中草藥化學圖像數據庫 (香港浸會大學中醫藥學院) （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）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

[17]

[18]

[19]

[20]

PROFILPELAJAR.COM

丁香油酚

性質

物理性質

化學性質

製備

用途

危害

含有丁香油酚的植物

參見

參考文獻

外部連結

Read other articles:

Liste des comtes de Fezensac

Kongres Nasional Partai Komunis Tiongkok ke-11

Oliver Hilmes

Scottish Premier League 2007-2008

University of Indonesia

Mario Vicini

Pierre-Morains

土库曼斯坦总统

Spanish East Indies

Pringapus, Semarang

Battle of Ridgeway

Australian and New Zealand Army Corps

Moor Abbey

Women for Trump

Corruption in South Africa

Bob Pettit

K. Pandiarajan

Kuwait Basketball Association

Ukraine au Concours Eurovision de la chanson 2017

マイタケ