棉酚

棉酚


IUPAC名 2,2′-bis-(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
英文名	Gossypol
识别
CAS号	303-45-7 ^Y
PubChem	3503
ChemSpider	3383
SMILES	CC(C)c2c1cc(C)c(c(c4O)c(C)cc3c4c(C=O) c(O)c(O)c3C(C)C)c(O)c1c(C=O)c(O)c2O
InChI	1/C30H30O8/c1-11(2)19-15-7- 13(5)21(27(35)23(15)17(9- 31)25(33)29(19)37)22- 14(6)8-16-20(12(3)4)30(38) 26(34)18(10-32)24(16) 28(22)36/h7-12,33-38H,1-6H3
InChIKey	QBKSWRVVCFFDOT-UHFFFAOYAH
KEGG	C07667
IUPHAR配体	4204
性质
化学式	C₃₀H₃₀O₈
摩尔质量	518.563 g·mol⁻¹
外观	棕色固体
熔点	177～182 °C (分解)
危险性
欧盟危险性符号有害 Xn
警示术语	R：R22, R40
安全术语	S：S22, S36
致死量或浓度：
LD₅₀（中位剂量）	2315 mg/kg (大鼠经口)^[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

棉酚（英語：Gossypol）是一种存在于棉花的棉籽及棉根皮中的多酚类物质。

性质

黄色晶体，有三种晶形。有毒，难溶于水，微溶于石油醚，溶于稀碳酸钠溶液、氨水（同时缓慢分解）、甲醇、乙醇、乙醚、氯仿、二甲基甲酰胺。

制取

可从棉籽油中提取或通过化学方法合成得到。

用途

用作聚乙烯稳定剂、橡胶抗氧剂、杀虫剂等。

科学家在研究食用粗制棉籽油造成不育时，发现棉酚具有男用抗生育活性。后进行了大量动物试验和上万名受试者的临床观察后证实，棉酚有良好的抗生精功能，但也存在两个主要副作用——低血钾及潜在的不可逆性（永久不育）。它抗生精的主要机制是对睾丸生精上皮产生作用，抑制多种脱氢酶的活性，破坏生精上皮，从而导致精子畸形、死亡甚至无精。它是一个联萘衍生物，有阻转异构现象，但只有左旋体有抗生精功效，右旋体无效。

棉酚有已经确认的抗癌作用，正在被考虑逐步应用于临床。也有报道称具其有一定的抗病毒作用，但效果值得商榷。

毒性

棉酚是毒性物质，可造成人体红肿出血、食欲不振、神经失常、体重减轻、影响生育力。食用含棉酚较多的毛棉油会引起中毒，患者皮肤有剧烈的灼烧感，并伴有头晕、气喘、心慌和无力等症状。因此，未经特殊处理的毛棉油不可食用。^[2]

棉酚的毒性可通过湿热处理法消除。在该过程中，棉酚分子的醛基与蛋白质的氨基缩合生成“结合棉酚”，但蛋白质的营养价值在该过程中亦大大降低。可通过溶剂萃取法除去棉酚来弥补上述不足。^[2]

参考资料

^ Gossypol from cotton seeds. [2009-09-06]. （原始内容存档于2008-09-07）.
^ ^2.0 ^2.1 夏延斌主编. 食品化学. 北京: 中国轻工业出版社. 2001年6月: 383. ISBN 7-5019-3153-4.

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