桐油酸

β-桐油酸
	IUPAC名; (9E,11E,13E)-十八碳-9,11,13-三烯酸
識別
CAS號	544-73-0
PubChem	5282820
ChemSpider	4445947
SMILES	O=C(O)CCCCCCC\C=C\C=C\C=C\CCCC;
ChEBI	38384
性質
化學式	C18H30O2
摩爾質量	278.43 g·mol−1
熔點	71.5 °C（345 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

α-桐油酸
	IUPAC名; (9Z,11E,13E)-十八碳-9,11,13-三烯酸
識別
CAS號	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
性質
化學式	C18H30O2
摩爾質量	278.43 g/mol g·mol⁻¹
熔點	48 °C（321 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

桐油酸是一種十八碳不飽和脂肪酸，常見的有兩種順反異構體：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）。通常說的桐油酸指α-異構體。它存在於桐油中，由於其不飽和鍵的存在，使桐油呈現出乾性油的性質，在空氣中形成緻密的漆膜。α-桐油酸存在於一些植物種子的提取物，桐油中含82%的α-桐油酸，苦瓜籽油中含60%。桐油酸學名的前綴Eleo-來自希臘語ἔλαιον，意為橄欖。^[1]

生化性質

早期對營養性質的研究記錄到α-桐油酸能顯著緩解脂肪酸缺乏的症狀，相比之下，另一種常見的不飽和脂肪酸α-亞麻酸（ALA）則不能。^[2]

α-桐油酸在大鼠體內轉化為共軛亞油酸。^[3]此化合物可誘導脂肪組織^[4]和HL-60白血病細胞（濃度20μM時）的細胞凋亡。^[5]給大鼠投放含0.01%苦瓜籽油（0.006% α-桐油酸）的飲食可抑制氧化偶氮甲烷誘導的癌變。^[6]

參考資料

^ 存档副本. [2017-03-24]. （原始內容存檔於2017-01-05）.
^ Burr, G.O.; Burr, M.M.; Miller, E. On the nature and role of the fatty acids essential in nutrition (PDF). J. Biol. Chem. 1932, 97 (1): 1–9 [2007-01-17]. （原始內容存檔 (PDF)於2007-02-21）.
^ Tsuzuki T, Kawakami Y, Abe R, et al. Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid. J Nutr. 1 August 2006, 136 (8): 2153–9. [2007-01-17]. PMID 16857834. （原始內容存檔於2007-02-08）.
^ Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. Regulation of apoptosis through arachidonate cascade in mammalian cells. 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.

[1] 存档副本. [2017-03-24]. （原始內容存檔於2017-01-05）.

[Burr-2] Burr, G.O.; Burr, M.M.; Miller, E. On the nature and role of the fatty acids essential in nutrition (PDF). J. Biol. Chem. 1932, 97 (1): 1–9 [2007-01-17]. （原始內容存檔 (PDF)於2007-02-21）.

[Tsuzuki-3] Tsuzuki T, Kawakami Y, Abe R, et al. Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid. J Nutr. 1 August 2006, 136 (8): 2153–9. [2007-01-17]. PMID 16857834. （原始內容存檔於2007-02-08）.

[Nishimura-4] Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. Regulation of apoptosis through arachidonate cascade in mammalian cells. 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.

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