十九酸

十九酸
	IUPAC名; 十九酸; Nonadecanoic acid
别名	Nonadecylic acid
识别
CAS号	646-30-0
PubChem	12591
ChemSpider	12071
SMILES	O=C(O)CCCCCCCCCCCCCCCCCC;
Beilstein	1786261
ChEBI	39246
性质
化学式	CH3(CH2)17COOH
摩尔质量	298.50382 g/mol g·mol⁻¹
外观	白色片状或粉末
熔点	68—70 °C（341—343 K）
沸点	227-230 °C（10 mmHg） ; 297°C (100 mmHg)
溶解性（水）	难溶
危险性
警示术语	R：R36/37/38
安全术语	S：S26
	GHS危险性符号;
GHS提示词	警告
H-术语	H315, H319, H335
P-术语	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
主要危害	具刺激性 (Xi)
相关物质
相关化学品	十八酸; 二十酸
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

十九酸（Nonadecanoic acid）是一种有机化合物，化学式为C H₃(CH₂)₁₇COOH。在自然界中，它存在于莳萝^[2]和红藻^[3]等植物中。

合成

十九酸可由1-二十烯经高锰酸钾在酸性条件下氧化制得，产物经重结晶提纯。^[4]

反应

十九酸和N-羟基丁二酰亚胺在1-乙基-(3-二甲基氨基丙基)碳二亚胺存在下于二氯甲烷中反应，可以得到N-十九酸丁二酰亚胺。^[5]它和叠氮化钠在二(甲氧基乙基)氨基三氟化硫、二异丙基乙胺存在下反应，可以得到十九酰叠氮。^[6]它在四氢呋喃中和氢化铝锂回流反应，可以被还原，得到1-十九烷醇。^[7]

参考文献

^ Fierz-David, H. E.; Kuster, W. Homologous series of acylated azo dyes from o- and p-acylaminophenols and 1,7-acylamino naphthols. Helvetica Chimica Acta. 1939, 22: 82–112. ISSN 0018-019X.
^ W. M. Amin, A. A. Sleem. Chemical And Biological Study Of Aerial Parts Of Dill (Anethum Graveolens L.). Egyptian Journal of Biomedical Sciences. 2007, 23: 73–90 [2023-07-11]. doi:10.4314/ejbs2.v23i1.40296. （原始内容存档于2023-07-11）.
^ S. Siddqiui; S. B. Naqvi Shyum; K. Usmanghani; M. Shameel. Antibacterial activity and fatty acid composition of the extract from Hypnea musciformis (Gigartinales, Rhodophyta). Pak J Pharm Sci. 1993, 6 (1): 45–51 [2023-07-11]. （原始内容存档于2023-07-11）.
^ Carboxylic acids from the oxidation of terminal alkenes by permanganate: nonadecanoic acid. Org. Synth. 1981, 60 (11) [2023-07-10]. doi:10.15227/orgsyn.060.0011. （原始内容存档于2023-07-10）.
^ Yingyongnarongkul, B. E., Radchatawedchakoon, W., Krajarng, A., Watanapokasin, R., & Suksamrarn, A. High transfection efficiency and low toxicity cationic lipids with aminoglycerol–diamine conjugate. Bioorganic & Medicinal Chemistry. 2009, 17 (1): 176–188. doi:10.1016/j.bmc.2008.11.003.
^ Kangani, C. O., Day, B. W., & Kelley, D. E. Direct, facile synthesis of acyl azides and nitriles from carboxylic acids using bis (2-methoxyethyl) aminosulfur trifluoride. Tetrahedron letters 48 (34): 5933–5937. 2007. doi:10.1016/j.tetlet.2007.06.119.
^ Juma'a R. Al Dulayymi; Mark S. Baird; Evan Roberts. The synthesis of a single enantiomer of a major α-mycolic acid of M. tuberculosis. Tetrahedron: 11939–11951. doi:10.1016/j.tet.2005.09.056.

拓展阅读

A. Mulero; I. Cachadiña; E. L. Sanjuán. Recommended Correlations for the Surface Tension of Aliphatic, Carboxylic, and Polyfunctional Organic Acids. Journal of Physical and Chemical Reference Data. 2016, 45 (3): 033105 [2023-07-11]. doi:10.1063/1.4959989. （原始内容存档于2023-07-11）.

Wei-Cheng Wang, William L. Roberts, Larry F. Stikeleather. Hydrocarbon Fuels From Gas Phase Decarboxylation of Hydrolyzed Free Fatty Acid. J. Energy Resour. Technol. 2012, 134 (3): 032203. doi:10.1115/1.4006867.

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[1] Fierz-David, H. E.; Kuster, W. Homologous series of acylated azo dyes from o- and p-acylaminophenols and 1,7-acylamino naphthols. Helvetica Chimica Acta. 1939, 22: 82–112. ISSN 0018-019X.

[2] W. M. Amin, A. A. Sleem. Chemical And Biological Study Of Aerial Parts Of Dill (Anethum Graveolens L.). Egyptian Journal of Biomedical Sciences. 2007, 23: 73–90 [2023-07-11]. doi:10.4314/ejbs2.v23i1.40296. （原始内容存档于2023-07-11）.

[3] S. Siddqiui; S. B. Naqvi Shyum; K. Usmanghani; M. Shameel. Antibacterial activity and fatty acid composition of the extract from Hypnea musciformis (Gigartinales, Rhodophyta). Pak J Pharm Sci. 1993, 6 (1): 45–51 [2023-07-11]. （原始内容存档于2023-07-11）.

[4] Carboxylic acids from the oxidation of terminal alkenes by permanganate: nonadecanoic acid. Org. Synth. 1981, 60 (11) [2023-07-10]. doi:10.15227/orgsyn.060.0011. （原始内容存档于2023-07-10）.

[5] Yingyongnarongkul, B. E., Radchatawedchakoon, W., Krajarng, A., Watanapokasin, R., & Suksamrarn, A. High transfection efficiency and low toxicity cationic lipids with aminoglycerol–diamine conjugate. Bioorganic & Medicinal Chemistry. 2009, 17 (1): 176–188. doi:10.1016/j.bmc.2008.11.003.

[6] Kangani, C. O., Day, B. W., & Kelley, D. E. Direct, facile synthesis of acyl azides and nitriles from carboxylic acids using bis (2-methoxyethyl) aminosulfur trifluoride. Tetrahedron letters 48 (34): 5933–5937. 2007. doi:10.1016/j.tetlet.2007.06.119.

[7] Juma'a R. Al Dulayymi; Mark S. Baird; Evan Roberts. The synthesis of a single enantiomer of a major α-mycolic acid of M. tuberculosis. Tetrahedron: 11939–11951. doi:10.1016/j.tet.2005.09.056.

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