壬二酸

壬二酸
	IUPAC名; nonanedioic acid
识别
CAS号	123-99-9
PubChem	2266
ChemSpider	2179
SMILES	O=C(O)CCCCCCCC(=O)O;
InChI	1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13);
InChIKey	BDJRBEYXGGNYIS-UHFFFAOYAK
ChEBI	48131
DrugBank	DB00548
KEGG	D03034
IUPHAR配体	7484
性质
化学式	C9H16O4
摩尔质量	188.22 g·mol−1
外观	白色粉末
密度	1.443 g/mL
熔点	109 °C（382 K）
沸点	286 °C（559 K）
溶解性（水）	2.14 g/L
pKa	4.550, 5.498
药理学
ATC代码	D10AX03（D10）
药品分级
给药途径	外用
	药代动力学：
生物利用度	极低
生物半衰期	12小时
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

壬二酸（又称杜鹃花酸）（英语：Azelaic acid，缩写AzA）是一种饱和二羧酸，化学式为HOOC(CH₂)₇COOH。在标准状态下，纯壬二酸呈白色粉末状。壬二酸自然存在于小麦、黑麦和大麦等榖物中。壬二酸可作为聚合物和增塑剂等化工产品的前体，它也是外用抗痤疮药物和某些头发和皮肤养护剂的成分。^[2]

制备[编辑]

在工业上，壬二酸可透过油酸的臭氧分解生产，而过程的副产品为壬酸。生活在正常皮肤上的真菌秕糠马拉癣菌会自然分泌壬二酸，而壬二酸也是壬酸的细菌分解产物。

9-十八碳烯酸经过强氧化剂（如高锰酸钾氧化）可以制得壬二酸。^[3]

生物作用[编辑]

在植物中，壬二酸是感染后防御反应中所涉及的一种植物激素。^[4]它能诱导水杨酸的积累，而水杨酸则是植物防御反应的重要组成部分。^[5]

应用[编辑]

聚合物及相关材料[编辑]

壬二酸酯可用于润滑剂和增塑剂。在润滑剂工业中，它可用作锂润滑脂的增稠剂。壬二酸与六亚甲基二胺的共聚物是特种塑料尼龙-6,9。^[2]

医学用途[编辑]

壬二酸可用于治疗轻度至中度的粉刺性和炎性痤疮。^[6]^[7]壬二酸能杀死感染毛孔的痤疮细菌，还会降低角蛋白的产生，而角蛋白是一种促进痤疮细菌生长的天然物质。^[8]由于它具有消炎作用，壬二酸还可以用作治疗玫瑰痤疮的外用药物。它可以治疗玫瑰痤疮引起的肿块和肿胀。壬二酸的作用机制是通过抑制过度活跃的蛋白酶活性，该蛋白酶能将导管素转化为抗微生物肽LL-37。^[9]壬二酸也可用于治疗皮肤色素沉著，包括黄褐斑和炎症后色素过度沉著，尤其是对于那些肤色较深的人。它也被推荐作为对苯二酚的代替品。^[10]作为酪氨酸酶抑制剂，壬二酸可抑制黑色素的合成。^[11]

与治疗脱发药物非那甾胺和度他雄胺（英语：dutasteride）相似的是，壬二酸也是一种有效的5α还原酶抑制剂。^[12]

参考文献[编辑]

^ ^1.0 ^1.1 Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH₃)₄NCl(aq), and (C₂H₅)₄NI(aq) at Different Ionic Strengths and at t = 25 °C. J. Chem. Eng. Data. 2006, 51 (5): 1660–1667. doi:10.1021/je060132t.
^ ^2.0 ^2.1 Cornils, Boy; Lappe, Peter. Dicarboxylic Acids, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2006. doi:10.1002/14356007.a08_523.
^ Shi, Chunwei; Zhou, Wenfeng; Zhao, Shanlin; et al. A method for synthesis of azelaic acid by combined oxidation with hydrogen peroxide and potassium permanganate[P]. CN 104447279. 2014.
^ Sarah Everts. Vegetative Warfare. Chemical & Engineering News. 2011-01-31, 89 (5): 53–55 [2018-10-21]. （原始内容存档于2015-02-25）.
^ Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. Priming in Systemic Plant Immunity. Science. 2009, 324 (5923): 89–91. Bibcode:2009Sci...324...89W. PMID 19342588. doi:10.1126/science.1170025.
^ Azelaic Acid for Acne. [2018-10-21]. （原始内容存档于2015-07-10）.
^ Azelaic acid topical. Drugs.com. [2018-10-21]. （原始内容存档于2017-10-15）.
^ Liu, R. H.; Smith, M. K.; Basta, S. A.; Farmer, E. R. Azelaic acid in the treatment of papulopustular rosacea – A systematic review of randomized controlled trials. Arch. Dermatol. 2006, 142 (8): 1047–1052. PMID 16924055. doi:10.1001/archderm.142.8.1047.
^ Reinholz, M.; Ruzicka, T.; Schauber, J. Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease. Annals of Dermatology. 2012, 24 (2): 126–135. PMC 3346901 . PMID 22577261. doi:10.5021/ad.2012.24.2.126.
^ Draelos, Z. Skin lightening preparations and the hydroquinone controversy. Dermatol. Ther. Sep–Oct 2007, 20 (5): 308–313. PMID 18045355. doi:10.1111/j.1529-8019.2007.00144.x.
^ Grimes, Pearl E. Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. 2007-07-01: 74 ff. [2011-08-09]. ISBN 978-0-7817-8403-0. （原始内容存档于2019-08-12）.
^ Stamatiadis, D; Bulteau-Portois, Marie-Claire; Mowszowicz, Irene. Inhibition of 5α-reductase activity in human skin by zinc and azelaic acid. British Journal of Dermatology. 1988, 119 (5): 627–32. PMID 3207614. doi:10.1111/j.1365-2133.1988.tb03474.x.

外部链接[编辑]

DermNet（英语：New Zealand Dermatological Society） treatments/azelaic-acid

Azelaic Acid Topical （页面存档备份，存于互联网档案馆）

[pka-1] 1.0 ^1.1 Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH₃)₄NCl(aq), and (C₂H₅)₄NI(aq) at Different Ionic Strengths and at t = 25 °C. J. Chem. Eng. Data. 2006, 51 (5): 1660–1667. doi:10.1021/je060132t.

[Boy-2] 2.0 ^2.1 Cornils, Boy; Lappe, Peter. Dicarboxylic Acids, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2006. doi:10.1002/14356007.a08_523.

[3] Shi, Chunwei; Zhou, Wenfeng; Zhao, Shanlin; et al. A method for synthesis of azelaic acid by combined oxidation with hydrogen peroxide and potassium permanganate[P]. CN 104447279. 2014.

[4] Sarah Everts. Vegetative Warfare. Chemical & Engineering News. 2011-01-31, 89 (5): 53–55 [2018-10-21]. （原始内容存档于2015-02-25）.

[5] Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. Priming in Systemic Plant Immunity. Science. 2009, 324 (5923): 89–91. Bibcode:2009Sci...324...89W. PMID 19342588. doi:10.1126/science.1170025.

[6] Azelaic Acid for Acne. [2018-10-21]. （原始内容存档于2015-07-10）.

[drugs.com-7] Azelaic acid topical. Drugs.com. [2018-10-21]. （原始内容存档于2017-10-15）.

[8] Liu, R. H.; Smith, M. K.; Basta, S. A.; Farmer, E. R. Azelaic acid in the treatment of papulopustular rosacea – A systematic review of randomized controlled trials. Arch. Dermatol. 2006, 142 (8): 1047–1052. PMID 16924055. doi:10.1001/archderm.142.8.1047.

[9] Reinholz, M.; Ruzicka, T.; Schauber, J. Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease. Annals of Dermatology. 2012, 24 (2): 126–135. PMC 3346901 . PMID 22577261. doi:10.5021/ad.2012.24.2.126.

[10] Draelos, Z. Skin lightening preparations and the hydroquinone controversy. Dermatol. Ther. Sep–Oct 2007, 20 (5): 308–313. PMID 18045355. doi:10.1111/j.1529-8019.2007.00144.x.

[Grimes2007-11] Grimes, Pearl E. Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. 2007-07-01: 74 ff. [2011-08-09]. ISBN 978-0-7817-8403-0. （原始内容存档于2019-08-12）.

[pmid3207614-12] Stamatiadis, D; Bulteau-Portois, Marie-Claire; Mowszowicz, Irene. Inhibition of 5α-reductase activity in human skin by zinc and azelaic acid. British Journal of Dermatology. 1988, 119 (5): 627–32. PMID 3207614. doi:10.1111/j.1365-2133.1988.tb03474.x.

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