油酸

油酸
	IUPAC名; (9Z)-octadec-9-enoic acid; (9Z)-9-十八碳烯酸
識別
CAS號	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配體	1054
性質
化學式	C18H34O2
莫耳質量	282.4614 g·mol⁻¹
外觀	無色至淡黃色液體
密度	0.895 g/mL
熔點	13-14 °C (286 K)
沸點	360 °C (633 K) (760mm Hg)
溶解性（水）	不溶
溶解性（甲醇）	可溶
危險性
MSDS	ScienceLab.com
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

油酸（英語：Oleic acid）是一種單不飽和 Omega-9 脂肪酸，存在於動植物體內。化學式C₁₈H₃₄O₂ ，結構簡式 CH₃(CH₂)₇CH = CH(CH₂)₇COOH。^[2]英文 oleic 源自拉丁文 oleum，意思是「油」，^[3]也特指「橄欖油」。^[4]油酸是自然界最常見的脂肪酸。^[5]油酸氫化得到硬脂酸；油酸的雙鍵反式異構體稱為反油酸。

自然界中

油酸占橄欖油的55-80%^[6]，軟質棕櫚油的39~46%^[7]，花生油的36-67%，芝麻油的15-20%。在動物脂肪中，油酸占雞與火雞脂肪的37-56%，豬油的44-47%。油酸也是人體脂肪組織中最豐富的脂肪酸。

化學性質

油酸具有羧酸和烯烴的性質。對碳碳雙鍵氧化可以使油酸分子斷裂，生成醛、酮或羧酸。油酸還可以發生還原反應生成醇。暴露於空氣中的油酸就會緩慢發生上述氧化反應，此過程稱為酸敗反應。

營養與生理影響研究

在動物實驗下，用相對高油酸油脂餵食可使有高血壓大鼠血壓降低^[8]。亦有研究指出可透過抑制細胞增生達到抗癌效果^[9]、調控發炎反應等作用，可應用於發炎、免疫反應、心血管疾病、皮膚修復及感染等方面^[10]。

有研究顯示當攝取高膽固醇飲食可增加酵素活性增加細胞膜上單元不飽和脂肪酸比例，例如油酸，提高乳腺癌發生的可能性。^[11]

參考資料

^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
^ Bishop, Paul L. (2000). Pollution Prevention: Chapter 2 - Properties and Fates of Environmental Contaminants 網際網路檔案館的存檔，存檔日期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]. （原始內容存檔於2020-12-06）.
^ 9-Octadecenoic acid. PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018 [19 July 2018]. （原始內容存檔於2015-12-13）.
^ Li, Thomas S. C. (1999). Sea buckthorn: New crop opportunity （頁面存檔備份，存於網際網路檔案館）, 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. （頁面存檔備份，存於網際網路檔案館）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. （頁面存檔備份，存於網際網路檔案館）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. （原始內容存檔於2008-12-18）.

外部連結

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 網際網路檔案館的存檔，存檔日期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]. （原始內容存檔於2020-12-06）.

[5] 9-Octadecenoic acid. PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018 [19 July 2018]. （原始內容存檔於2015-12-13）.

[6] Li, Thomas S. C. (1999). Sea buckthorn: New crop opportunity （頁面存檔備份，存於網際網路檔案館）, 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. （頁面存檔備份，存於網際網路檔案館）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. （頁面存檔備份，存於網際網路檔案館）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. （原始內容存檔於2008-12-18）.

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