油酸

油酸
	IUPAC名; (9Z)-octadec-9-enoic acid; (9Z)-9-十八碳烯酸
识别
CAS号	112-80-1
ChemSpider	393217
SMILES	CCCCCCCC\C=C/CCCCCCCC(O)=O;
InChI	1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-;
InChIKey	ZQPPMHVWECSIRJ-KTKRTIGZBB
IUPHAR配体	1054
性质
化学式	C18H34O2
摩尔质量	282.4614 g·mol⁻¹
外观	无色至淡黄色液体
密度	0.895 g/mL
熔点	13-14 °C (286 K)
沸点	360 °C (633 K) (760mm Hg)
溶解性（水）	不溶
溶解性（甲醇）	可溶
危险性
MSDS	ScienceLab.com
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

油酸（英语：Oleic acid）是一种单不饱和 Omega-9 脂肪酸，存在于动植物体内。化学式C₁₈H₃₄O₂ ，结构简式 CH₃(CH₂)₇CH = CH(CH₂)₇COOH。^[2]英文 oleic 源自拉丁文 oleum，意思是“油”，^[3]也特指“橄榄油”。^[4]油酸是自然界最常见的脂肪酸。^[5]油酸氢化得到硬脂酸；油酸的双键反式异构体称为反油酸。

自然界中

油酸占橄榄油的55-80%^[6]，软质棕榈油的39~46%^[7]，花生油的36-67%，芝麻油的15-20%。在动物脂肪中，油酸占鸡与火鸡脂肪的37-56%，猪油的44-47%。油酸也是人体脂肪组织中最丰富的脂肪酸。

化学性质

油酸具有羧酸和烯烃的性质。对碳碳双键氧化可以使油酸分子断裂，生成醛、酮或羧酸。油酸还可以发生还原反应生成醇。暴露于空气中的油酸就会缓慢发生上述氧化反应，此过程称为酸败反应。

营养与生理影响研究

在动物实验下，用相对高油酸油脂喂食可使有高血压大鼠血压降低^[8]。亦有研究指出可透过抑制细胞增生达到抗癌效果^[9]、调控发炎反应等作用，可应用于发炎、免疫反应、心血管疾病、皮肤修复及感染等方面^[10]。

有研究显示当摄取高胆固醇饮食可增加酵素活性增加细胞膜上单元不饱和脂肪酸比例，例如油酸，提高乳腺癌发生的可能性。^[11]

参考资料

^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
^ Bishop, Paul L. (2000). Pollution Prevention: Chapter 2 - Properties and Fates of Environmental Contaminants 互联网档案馆的存档，存档日期2008-09-10., instructional slides to accompany Pollution Prevention:Fundamentals and Practice, by Paul L. Bishop (ISBN 0-07-366147-3). Retrieved 2005-03-07.
^ Bailey and Bailey, Dorothy and Kenneth. An Etymological Dictionary of Chemistry and Mineralogy. Nature. 1929, 124 (3134): 789–790. Bibcode:1929Natur.124..789V. S2CID 4024133. doi:10.1038/124789b0.
^ 存档副本. [2021-03-12]. （原始内容存档于2020-12-06）.
^ 9-Octadecenoic acid. PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018 [19 July 2018]. （原始内容存档于2015-12-13）.
^ Li, Thomas S. C. (1999). Sea buckthorn: New crop opportunity （页面存档备份，存于互联网档案馆）, from Perspectives on new crops and new uses by J. Janeck (ed.) Retrieved 2006-10-28.
^ STANDARD FOR NAMED VEGETABLE OILS CODEX STAN 210-1999
^ Terés, S; Barceló-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escribá, Pv. Oleic acid content is responsible for the reduction in blood pressure induced by olive oil. Proceedings of the National Academy of Sciences of the United States of America. September 2008. PMID 18772370. doi:10.1073/pnas.0807500105.
^ Carrillo, M. del M. Cavia and S. R. Alonso-Torre. 2012.Antitumor effect of oleic acid; mechanisms of action: a review. （页面存档备份，存于互联网档案馆）Nutrición Hospitalaria. 27(5): 1860-1865.
^ H. Sales-Campos, P.R. Souza, B.C. Peghini, J. S. da Silva, C. R. Cardoso CR. 2012.An overview of the modulatory effects of oleic acid in health and disease. （页面存档备份，存于互联网档案馆）Mini-Reviews in Medicinal Chemistry. 13(2): 201-210.
^ Valeria Pala, Vittorio Krogh, Paola Muti, Véronique Chajès, Elio Riboli, Andrea Micheli, Mitra Saadatian, Sabina Sieri, Franco Berrino. Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study. JNCL. Jul 18, 2001, 93 (14): 1088 [2008-11-30]. PMID 11459870. （原始内容存档于2008-12-18）.

外部链接

NIST Chemistry Webbook

[1] Oleic acid, Chemical Laboratory Information Profile, American Chemical Society

[2] Bishop, Paul L. (2000). Pollution Prevention: Chapter 2 - Properties and Fates of Environmental Contaminants 互联网档案馆的存档，存档日期2008-09-10., instructional slides to accompany Pollution Prevention:Fundamentals and Practice, by Paul L. Bishop (ISBN 0-07-366147-3). Retrieved 2005-03-07.

[3] Bailey and Bailey, Dorothy and Kenneth. An Etymological Dictionary of Chemistry and Mineralogy. Nature. 1929, 124 (3134): 789–790. Bibcode:1929Natur.124..789V. S2CID 4024133. doi:10.1038/124789b0.

[4] 存档副本. [2021-03-12]. （原始内容存档于2020-12-06）.

[5] 9-Octadecenoic acid. PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018 [19 July 2018]. （原始内容存档于2015-12-13）.

[6] Li, Thomas S. C. (1999). Sea buckthorn: New crop opportunity （页面存档备份，存于互联网档案馆）, from Perspectives on new crops and new uses by J. Janeck (ed.) Retrieved 2006-10-28.

[7] STANDARD FOR NAMED VEGETABLE OILS CODEX STAN 210-1999

[8] Terés, S; Barceló-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escribá, Pv. Oleic acid content is responsible for the reduction in blood pressure induced by olive oil. Proceedings of the National Academy of Sciences of the United States of America. September 2008. PMID 18772370. doi:10.1073/pnas.0807500105.

[9] Carrillo, M. del M. Cavia and S. R. Alonso-Torre. 2012.Antitumor effect of oleic acid; mechanisms of action: a review. （页面存档备份，存于互联网档案馆）Nutrición Hospitalaria. 27(5): 1860-1865.

[10] H. Sales-Campos, P.R. Souza, B.C. Peghini, J. S. da Silva, C. R. Cardoso CR. 2012.An overview of the modulatory effects of oleic acid in health and disease. （页面存档备份，存于互联网档案馆）Mini-Reviews in Medicinal Chemistry. 13(2): 201-210.

[11] Valeria Pala, Vittorio Krogh, Paola Muti, Véronique Chajès, Elio Riboli, Andrea Micheli, Mitra Saadatian, Sabina Sieri, Franco Berrino. Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study. JNCL. Jul 18, 2001, 93 (14): 1088 [2008-11-30]. PMID 11459870. （原始内容存档于2008-12-18）.

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