甲萘醌

甲萘醌
	IUPAC名; 2-Methylnaphthalene-1,4-dione
别名	2-甲基-1,4-萘醌; 维生素K3
识别
CAS号	58-27-5
PubChem	4055
ChemSpider	3915
SMILES	O=C\2c1c(cccc1)C(=O)/C(=C/2)C;
InChI	1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3;
InChIKey	MJVAVZPDRWSRRC-UHFFFAOYAY
ChEBI	28869
DrugBank	DB00170
KEGG	D02335
性质
化学式	C11H8O2
摩尔质量	172.18 g·mol−1
外观	亮黄色晶体
密度	1.225 g/cm3
熔点	105-107 °C（378-380 K）
溶解性（水）	不可溶
药理学
ATC代码	B02BA02（B02）
药品分级
妊娠分类	Contraindicated in India
给药途径	口服; 静脉注射; 肌肉注射;
危险性
	致死量或浓度：
LD50（中位剂量）	0.5 g/kg（小鼠，口服）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

甲萘醌（英语：Menadione，2-甲基-1,4-萘醌，有时也称作维生素K₃）^[2]是一种化学式为C₆H₄(CO)₂C₂H(CH₃)的有机化合物。

此物在体内可由NQO1和UBIAD1转化为维生素K（K2, MK-4），^[3]但过量使用会导致活性氧类产生。^[4]K3一般是合成产生，用作动物饲料和低收入地区的人类营养补充剂。根据欧洲食品安全局的报告，K3用于动物饲料时从未导致过毒性产生。^[5]

口服天然形式的维生素K1、K2也会在体内生成K3。^[2]K3可以穿透血脑屏障。^[3]

参考文献

^ The Merck Index, 11th Edition, 5714
^ ^2.0 ^2.1 Hirota, Yoshihisa; Tsugawa, Naoko; Nakagawa, Kimie; Suhara, Yoshitomo; Tanaka, Kiyoshi; Uchino, Yuri; Takeuchi, Atsuko; Sawada, Natsumi; Kamao, Maya; Wada, Akimori; Okitsu, Takashi. Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats. The Journal of Biological Chemistry. 2013-11-15, 288 (46): 33071–33080. ISSN 1083-351X. PMC 3829156  . PMID 24085302. doi:10.1074/jbc.M113.477356  .
^ ^3.0 ^3.1 Shearer, Martin J.; Newman, Paul. Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. Journal of Lipid Research. March 2014, 55 (3): 345–362. ISSN 0022-2275. PMC 3934721  . PMID 24489112. doi:10.1194/jlr.R045559.
^ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD. Fox , 编. Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae. PLOS ONE. 2008, 3 (12): e3999. Bibcode:2008PLoSO...3.3999C. PMC 2600608  . PMID 19098979. doi:10.1371/journal.pone.0003999  .
^ EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP). Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species.. EFSA Journal. January 2014, 12 (1): 3532. doi:10.2903/j.efsa.2014.3532  .

外部链接

甲萘醌 in the Pesticide Properties DataBase (PPDB)

[1] The Merck Index, 11th Edition, 5714

[nat-2] 2.0 ^2.1 Hirota, Yoshihisa; Tsugawa, Naoko; Nakagawa, Kimie; Suhara, Yoshitomo; Tanaka, Kiyoshi; Uchino, Yuri; Takeuchi, Atsuko; Sawada, Natsumi; Kamao, Maya; Wada, Akimori; Okitsu, Takashi. Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats. The Journal of Biological Chemistry. 2013-11-15, 288 (46): 33071–33080. ISSN 1083-351X. PMC 3829156  . PMID 24085302. doi:10.1074/jbc.M113.477356  .

[:0-3] 3.0 ^3.1 Shearer, Martin J.; Newman, Paul. Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. Journal of Lipid Research. March 2014, 55 (3): 345–362. ISSN 0022-2275. PMC 3934721  . PMID 24489112. doi:10.1194/jlr.R045559.

[pmid19098979-4] Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD. Fox , 编. Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae. PLOS ONE. 2008, 3 (12): e3999. Bibcode:2008PLoSO...3.3999C. PMC 2600608  . PMID 19098979. doi:10.1371/journal.pone.0003999  .

[5] EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP). Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species.. EFSA Journal. January 2014, 12 (1): 3532. doi:10.2903/j.efsa.2014.3532  .

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甲萘醌^[1]


IUPAC名 2-Methylnaphthalene-1,4-dione
别名	2-甲基-1,4-萘醌维生素K₃
识别
CAS号	58-27-5 ^Y
PubChem	4055
ChemSpider	3915
SMILES	O=C\2c1c(cccc1)C(=O)/C(=C/2)C
InChI	1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey	MJVAVZPDRWSRRC-UHFFFAOYAY
ChEBI	28869
DrugBank	DB00170
KEGG	D02335
性质
化学式	C₁₁H₈O₂
摩尔质量	172.18 g·mol⁻¹
外观	亮黄色晶体
密度	1.225 g/cm³
熔点	105-107 °C（378-380 K）
溶解性（水）	不可溶
药理学
ATC代码	B02BA02（B02）
药品分级
妊娠分类	Contraindicated in India
给药途径	口服静脉注射肌肉注射
危险性
致死量或浓度：
LD₅₀（中位剂量）	0.5 g/kg（小鼠，口服）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。