桐油酸

β-桐油酸
	IUPAC名; (9E,11E,13E)-十八碳-9,11,13-三烯酸
识别
CAS号	544-73-0
PubChem	5282820
ChemSpider	4445947
SMILES	O=C(O)CCCCCCC\C=C\C=C\C=C\CCCC;
ChEBI	38384
性质
化学式	C18H30O2
摩尔质量	278.43 g·mol−1
熔点	71.5 °C（345 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

α-桐油酸
	IUPAC名; (9Z,11E,13E)-十八碳-9,11,13-三烯酸
识别
CAS号	506-23-0
ChemSpider	4444560
SMILES	O=C(O)CCCCCCC/C=C\C=C\C=C\CCCC;
InChI	1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7+,10-9-;
ChEBI	10275
性质
化学式	C18H30O2
	278.43 g/mol g·mol⁻¹
熔点	48 °C（321 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

桐油酸是一种十八碳不饱和脂肪酸，常见的有两种顺反异构体：α-桐油酸（(9Z,11E,13E)-十八碳-9,11,13-三烯酸）和β-桐油酸（(9E,11E,13E)-十八碳-9,11,13-三烯酸）。通常说的桐油酸指α-异构体。它存在于桐油中，由于其不饱和键的存在，使桐油呈现出干性油的性质，在空气中形成致密的漆膜。α-桐油酸存在于一些植物种子的提取物，桐油中含82%的α-桐油酸，苦瓜籽油中含60%。桐油酸学名的前缀Eleo-来自希腊语ἔλαιον，意为橄榄。[1]

生化性质

α-桐油酸占苦瓜油脂肪酸的60%

早期对营养性质的研究记录到α-桐油酸能显着缓解脂肪酸缺乏的症状，相比之下，另一种常见的不饱和脂肪酸α-亚麻酸（ALA）则不能。[2]

α-桐油酸在大鼠体内转化为共轭亚油酸。[3]此化合物可诱导脂肪组织[4]和HL-60白血病细胞（浓度20μM时）的细胞凋亡。[5]给大鼠投放含0.01%苦瓜籽油（0.006% α-桐油酸）的饮食可抑制氧化偶氮甲烷诱导的癌变。[6]

参考资料

. [2017-03-24]. （原始内容存档于2017-01-05）.
Burr, G.O.; Burr, M.M.; Miller, E. (PDF). J. Biol. Chem. 1932, 97 (1): 1–9 [2007-01-17]. （原始内容存档 (PDF)于2007-02-21）.
Tsuzuki T, Kawakami Y, Abe R, et al. . J Nutr. 1 August 2006, 136 (8): 2153–9. [2007-01-17]. PMID 16857834. （原始内容存档于2007-02-08）.
Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. . Appl Biochem Biotechnol. 2002,. 102-103 (1-6): 239–50. PMID 12396127. doi:10.1385/ABAB:102-103:1-6:239.
Masuko Kobori, Mayumi Ohnishi-Kameyama, Yukari Akimoto, Chizuko Yukizaki and Mitsuru Yoshida (2008) α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd. Journal of Agricultural and Food Chemistry, volume 56, issue 22, pages 10515–10520. doi:10.1021/jf8020877
H. Kohno, Y. Yasui, R. Suzuki, M. Hosokawa, K. Miyashita, T. Tanaka (2004), Dietary seed oil rich in conjugated linolenic acid from bitter melon inhibits azoxymethane-induced rat colon carcinogenesis through elevation of colonic PPAR γ expression and alteration of lipid composition. International Journal of Cancer, volume 110, pages 896–901.

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[1] . [2017-03-24]. （原始内容存档于2017-01-05）.

[Burr-2] Burr, G.O.; Burr, M.M.; Miller, E. (PDF). J. Biol. Chem. 1932, 97 (1): 1–9 [2007-01-17]. （原始内容存档 (PDF)于2007-02-21）.

[Tsuzuki-3] Tsuzuki T, Kawakami Y, Abe R, et al. . J Nutr. 1 August 2006, 136 (8): 2153–9. [2007-01-17]. PMID 16857834. （原始内容存档于2007-02-08）.

[Nishimura-4] Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. . Appl Biochem Biotechnol. 2002,. 102-103 (1-6): 239–50. PMID 12396127. doi:10.1385/ABAB:102-103:1-6:239.

[kob2008-5] Masuko Kobori, Mayumi Ohnishi-Kameyama, Yukari Akimoto, Chizuko Yukizaki and Mitsuru Yoshida (2008) α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd. Journal of Agricultural and Food Chemistry, volume 56, issue 22, pages 10515–10520. doi:10.1021/jf8020877

[kohno2004-6] H. Kohno, Y. Yasui, R. Suzuki, M. Hosokawa, K. Miyashita, T. Tanaka (2004), Dietary seed oil rich in conjugated linolenic acid from bitter melon inhibits azoxymethane-induced rat colon carcinogenesis through elevation of colonic PPAR γ expression and alteration of lipid composition. International Journal of Cancer, volume 110, pages 896–901.