丁香油酚

丁香油酚
	IUPAC名; 4-烯丙基-2-甲氧基苯酚
英文名	Eugenol
別名	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; 異丁香酚苯乙醚
識別
CAS號	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
性質
化學式	C10H12O2
摩爾質量	164.20 g·mol⁻¹
密度	1.06 g/cm3
熔點	−9 °C（264 K）
沸點	256 °C（529 K）
危險性
	歐盟危險性符號; 有害 Xn
警示術語	R：R22, R36/37/38, R38, R40, R42/43
安全術語	S：S23, S24/25, S26, S36
閃點	104℃
	若非註明，所有數據均出自標準狀態（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，富含於其精油中，如月桂油等^[1]^[2]。具有持久香氣，常作為香皂的香料。

Quick Facts 丁香油酚, 識別 ...

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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」源自丁香其中一個屬名——「Eugenia」（番櫻桃屬）。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]
長期暴露空氣中會變黑變稠黏，出現刺激性臭味。

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

過量攝取會出現心悸、頭暈、嘔吐、腹瀉、昏迷及抽搐等症狀，可引起皮炎及皮膚過敏^[8]。1993年，曾報道一名2歲男童服用5至10毫升丁香油酚後險些喪命。^[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]
（中文）ChemicalBook 丁香油酚（頁面存檔備份，存於互聯網檔案館）
[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]. （原始內容存檔於2011-10-24）.
[4]
（中文）丁香油酚的藥理作用（頁面存檔備份，存於互聯網檔案館）
[5]
「麻醉魚」是怎麼回事？ | 科學人 | 果殼網科技有意思. [2014-08-15]. （原始內容存檔於2015-04-15）.
[6]
丁香油麻醉魚？魚市場保全：行之有年. [2014-08-15]. （原始內容存檔於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]. （原始內容存檔於2016-02-23）.
[8]
Eugenol Oil Overdose （頁面存檔備份，存於互聯網檔案館）, 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.
[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.
[13]
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.
[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.
[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.
[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.
[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.
[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]. （原始內容存檔於2012-10-09）.
[20]
Lemon balm. University of Maryland Medical Center. [2010-12-07]. （原始內容存檔於2013-05-22）.

外部連結

（英文）Kegley, S.E., Hill, B.R., Orme S., Choi A.H., Toxicity Information for Eugenol（頁面存檔備份，存於互聯網檔案館） 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]. （原始內容存檔於2009-12-30）. (Eugenol entry on the Molecule of the Day blog)
丁子香酚 Eugenol （頁面存檔備份，存於互聯網檔案館）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]
（中文）ChemicalBook 丁香油酚（頁面存檔備份，存於互聯網檔案館）

[化學分子世界導覽一-2] [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] [3]
化工词典丁香油酚. [2011-05-20]. （原始內容存檔於2011-10-24）.

[Ref001-4] [4]
（中文）丁香油酚的藥理作用（頁面存檔備份，存於互聯網檔案館）

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

[6] [6]
丁香油麻醉魚？魚市場保全：行之有年. [2014-08-15]. （原始內容存檔於2014-08-15）.

[7] [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]. （原始內容存檔於2016-02-23）.

[8] [8]
Eugenol Oil Overdose （頁面存檔備份，存於互聯網檔案館）, New York Times Health Guide

[9] [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] [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] [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] [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]
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] [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] [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] [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] [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] [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] [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]. （原始內容存檔於2012-10-09）.

[20] [20]
Lemon balm. University of Maryland Medical Center. [2010-12-07]. （原始內容存檔於2013-05-22）.

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