丁香油酚

丁香酚
	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，所有数据均出自一般条件（25 ℃，100 kPa）下。

丁香[油]酚（英语：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酚。

性質[编辑]

物理性質[编辑]

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[编辑]

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[编辑]

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[编辑]

抗菌、麻醉和降血壓^[4]
製造香水、香精、精油、修飾劑和定香劑
製造局部麻醉藥

危害[编辑]

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^[5]。1993年，曾报道一名2岁男童服用5至10毫升丁香酚後险些喪命^[6]。
具有肝毒性，影響肝功能^[7]^[8]。

含有丁香酚的植物[编辑]

參見[编辑]

參考文獻[编辑]

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 （中文）ChemicalBook 丁香酚
^ 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.
^ 化工词典丁香酚
^ ^4.0 ^4.1 （中文）丁香酚的药理作用
^ Eugenol Oil Overdose, 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. doi:10.1136/adc.69.3.392. PMC 1029532. PMID 8215554.
^ 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. doi:10.1006/taap.1997.8348. PMID 9512727.
^ 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. doi:10.1016/S0300-483X(02)00194-4. PMID 12126794.
^ Pathak, S. B. et al.; Niranjan, K.; Padh, H.; Rajani, M. 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.
^ ^10.0 ^10.1 BULLERMAN, L. B. et al.; Lieu, F. Y.; Seier, Sally A. 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. doi:10.1016/S0308-8146(01)00161-3.
^ Kreydiyyeh, S. I. et al.; Usta, J; Copti, R. 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. doi:10.1016/S0278-6915(00)00073-9. PMID 10930696.
^ Dighe, V. V. et al.; Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H. 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. et al.; Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V. 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. 建议使用|displayauthors= (帮助);
^ 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. 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.
^ Lemon balm. University of Maryland Medical Center. [2010-12-07].

外部連結[编辑]

（英文）Kegley, S.E., Hill, B.R., Orme S., Choi A.H., Toxicity Information for Eugenol 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]. (Eugenol entry on the Molecule of the Day blog)

[ChemicalBook-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 （中文）ChemicalBook 丁香酚

[.E5.8C.96.E5.AD.B8.E5.88.86.E5.AD.90.E4.B8.96.E7.95.8C.E5.B0.8E.E8.A6.BD.E4.B8.80-2] 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] 化工词典丁香酚

[Ref001-4] 4.0 ^4.1 （中文）丁香酚的药理作用

[5] Eugenol Oil Overdose, New York Times Health Guide

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

[7] 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. doi:10.1006/taap.1997.8348. PMID 9512727.

[8] 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. doi:10.1016/S0300-483X(02)00194-4. PMID 12126794.

[tdmq-9] Pathak, S. B. et al.; Niranjan, K.; Padh, H.; Rajani, M. 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-10] 10.0 ^10.1 BULLERMAN, L. B. et al.; Lieu, F. Y.; Seier, Sally A. 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-11] 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. doi:10.1016/S0308-8146(01)00161-3.

[eccs-12] Kreydiyyeh, S. I. et al.; Usta, J; Copti, R. 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. doi:10.1016/S0278-6915(00)00073-9. PMID 10930696.

[qdec-13] Dighe, V. V. et al.; Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H. 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-14] Bennett, A. et al.; Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V. 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. 建议使用|displayauthors= (帮助);

[osc-15] 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. doi:10.1016/S0031-9422(98)00767-5.

[16] 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.

[17] Lemon balm. University of Maryland Medical Center. [2010-12-07].

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丁香油酚

目录

性質[编辑]

物理性質[编辑]

化學性質[编辑]

製備[编辑]

用途[编辑]

危害[编辑]

含有丁香酚的植物[编辑]

參見[编辑]

參考文獻[编辑]

外部連結[编辑]

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丁香酚


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 ^[1]
警示术语	R：R22, R36/37/38, R38, R40, R42/43^[1]
安全术语	S：S23, S24/25, S26, S36^[1]
闪点	104℃
若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。