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莽草酸

莽草酸

CAS号：138-59-0

英文名：Shikimic acid

分子式

C7H10O5

熔点

185-187°C(lit.)

密度

1.725 g/cm3

分子量

174.151

沸点

400.5ºC at 760 mmHg

溶解度

18 g/100 mL (20 ºC)

信号词

危险品标志

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化合物简介

莽草酸（3,4,5-三羟基-1-环己烯-1-甲酸）是一种易溶于水的白色晶体粉末。它因最早分离自日本莽草而得名，是一种植物和微生物的重要代谢产物。

基本信息

中文名称

莽草酸

英文名称

Shikimic acid

中文别名

(3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯-1-甲酸、(3R,4S,5R)-(-)-3,4,5-三羟基-1-环己烯羧酸

英文别名

(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid、3,4,5-Trihydroxycyclohex-1-enecarboxylic acid、(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid、(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid、Shikimic acid、Shikimic Acid

CAS号

138-59-0

分子式

C7H10O5

分子量

174.151

精确质量

174.053

PSA

97.99

LOGP

-1.5162

编号系统

MDL号

MFCD00066278

BRN号

4782717

PubChem号

24899647

RTECS号

GW4600000

EINECS号

205-334-2

物化性质

外观与性状

白色粉末

密度

1.725 g/cm3

沸点

400.5ºC at 760 mmHg

熔点

185-187°C(lit.)

闪点

210.1ºC

折射率

-180 ° (C=1, H2O)

水溶解性

18 g/100 mL (20 ºC)

稳定性

Stable under normal temperatures and pressures.

储存条件

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

蒸汽压

4.45E-08mmHg at 25°C

安全信息

RTECS号

GW4600000

安全说明

S22-S24/25

危险类别码

R36/37/38

WGK Germany

3

海关编码

29181980

危险品标志

Xi

生产方法及用途

生产方法

莽草酸是从中药八角茴香中提取的一种单体化合物。

用途

莽草酸通过影响花生四烯酸代谢，抑制血小板聚集，抑制动、静脉血栓及脑血栓形成，并具有有抗炎、镇痛作用，还可作为抗病毒和抗癌药物中间体。本品多用做制药中间体，具有一定刺激性，不宜直接使用。有机合成

合成路线

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甲基(-)-莽草酸

甲基(-)-莽草酸

莽草酸

3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid

3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid

对羟基苯甲酸

对羟基苯甲酸

上游原料

共找到67个上游原料 >

methyl (1S,5R,6S)-5-(hexanoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate

methyl (1S,5R,6S)-5-(hexanoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate

(1S,4R,4aS,5R,8S,8aR)-8-(methoxymethoxy)-1,4,4a,5,8,8a-hexahydro-1,4-methanonaphthalen-5-yl acetate

(1S,4R,4aS,5R,8S,8aR)-8-(methoxymethoxy)-1,4,4a,5,8,8a-hexahydro-1,4-methanonaphthalen-5-yl acetate

methyl (1α,6α)-2β-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-4-carboxylate

methyl (1α,6α)-2β-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-4-carboxylate

(1R,2aR,2a1S,5S,5aS,6R,7aS,8R)-8-bromo-5-(methoxymethoxy)-1,2a,2a1,5,5a,6,7,7a-octahydro-1,6-methanoindeno[7,1-bc]furan

(1R,2aR,2a1S,5S,5aS,6R,7aS,8R)-8-bromo-5-(methoxymethoxy)-1,2a,2a1,5,5a,6,7,7a-octahydro-1,6-methanoindeno[7,1-bc]furan

(-)-shikimic acid 3-O-gallate

(-)-shikimic acid 3-O-gallate

(3aR,7R,7aS)-7-Hydroxy-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

(3aR,7R,7aS)-7-Hydroxy-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

下游产品

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3-羟基苯甲酸甲酯

3-羟基苯甲酸甲酯

磷酸奥司他韦

磷酸奥司他韦

奥司他韦

(3R,4S,5R)-5-amino-3,4-dihydroxycyclohexene-1-carboxylic acid

(3R,4S,5R)-5-amino-3,4-dihydroxycyclohexene-1-carboxylic acid

甲基(-)-莽草酸

甲基(-)-莽草酸

methyl (3R,5R)-3-acetoxy-5-((tert-butyldimethylsilyl)oxy)-4-oxocyclohex-1-ene-1-carboxylate

methyl (3R,5R)-3-acetoxy-5-((tert-butyldimethylsilyl)oxy)-4-oxocyclohex-1-ene-1-carboxylate

上游原料

methyl (1S,5R,6S)-5-(hexanoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate (1S,4R,4aS,5R,8S,8aR)-8-(methoxymethoxy)-1,4,4a,5,8,8a-hexahydro-1,4-methanonaphthalen-5-yl acetate methyl (1α,6α)-2β-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-4-carboxylate (1R,2aR,2a1S,5S,5aS,6R,7aS,8R)-8-bromo-5-(methoxymethoxy)-1,2a,2a1,5,5a,6,7,7a-octahydro-1,6-methanoindeno[7,1-bc]furan (-)-shikimic acid 3-O-gallate (3aR,7R,7aS)-7-Hydroxy-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (1R,5R,6R)-methyl 5-(benzoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate (1S,2R,6R)-4-(ethoxycarbonyl)-6-(4-nitrobenzoyloxy)-cyclohex-3-ene-1,2-diyl diacetate (3aR,5R,5aR,8aS,8bS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-dimethylamino-7,7-dimethyl-tetrahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole-3a-carboxylic acid methyl ester (1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol (3aR,4S,5R,7R,7aR)-methyl 5-acetoxy-7-((tert-butyldimethylsilyl)oxy)-4-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate 葡萄糖 (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate (1R,3S,4R,5R)-methyl 1-acetoxy-5-((tert-butyldimethylsilyl)oxy)-3,4-dihydroxy-2-oxocyclohexanecarboxylate (1R,4S,4aR,8R,8aS)-methyl 8-((tert-butyldimethylsilyl)oxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methanonaphthalene-6-carboxylate methyl (3R,5R)-3-acetoxy-5-((tert-butyldimethylsilyl)oxy)-4-oxocyclohex-1-ene-1-carboxylate D-葡萄糖 (3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester (3R,4R,5R)-3-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (-)-shikimic acid 3,4-O-digallate (-)-3-去氢莽草酸 (1R,2aS,2a1S,3R,4S,5R,5aS,6R,7aS,8R)-8-bromo-3,4,5-tris(methoxymethoxy)decahydro-1,6-methanoindeno[7,1-bc]furan methyl (1R,4S,4aR,6R,8R,8aS)-6-acetoxy-8-((tert-butyldimethylsilyl)oxy)-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6-carboxylate tert-butyl(((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-((phenylthio)methyl)-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)oxy)dimethylsilane Acetic acid (3aS,4R,7aR)-6-formyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester (-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo[4,1,0]hept-3-ene-4-carboxylate (1S,5R,6S)-methyl 5-(hexanoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate (-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one methyl (benzyl 5,6-dideoxy-6-dimethoxyphosphoryl-2,3-O-isopropylidene-α-D-lyxo-heptofuranosid)uronate (3R,4S,5R)-5-acetoxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid (3R-(3alpha,4alpha,5beta))-5-((3-(3,4-二羟基苯基)-1-氧代-2-丙烯基)氧基)-3,4-二羟基-1-环己烯-1-羧酸 t-butyl (benzyl 5,6-dideoxy-6-dimethoxyphosphoryl-2,3-O-isopropylidene-α-D-lyxo-heptofuranosid)uronate (3aR,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 (3aS,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (3aR,7R,7aR)-methyl 7-((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 磷烯醇丙酮酸 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylic acid methyl (3aR,4S,5R,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-4,5-dihydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate 甲基(-)-莽草酸 methyl (1R,5R)-1-acetoxy-5-((tert-butyldimethylsilyl)oxy)-2-oxocyclohex-3-ene-1-carboxylate (1S,2R,6R)-6-hydroxy-4-(methoxycarbonyl)cyclohex-3-ene-1,2-diyl diacetate 右旋奎宁酸 (1S,4R,4aS,5S,6R,7S,8R,8aR)-6,7,8-tris(methoxymethoxy)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalen-5-ol (3R,4S,5R)-4-hydroxy-3,5-bis[(3,4,5-trihydroxybenzoyl)oxy]cyclohexene-1-carboxylic acid

下游产品

3-羟基苯甲酸甲酯磷酸奥司他韦奥司他韦 (3R,4S,5R)-5-amino-3,4-dihydroxycyclohexene-1-carboxylic acid 甲基(-)-莽草酸 methyl (3R,5R)-3-acetoxy-5-((tert-butyldimethylsilyl)oxy)-4-oxocyclohex-1-ene-1-carboxylate 吲唑 5-叠氮奥塞米韦间羟基苯甲酸对羟基苯甲酸右旋奎宁酸莽草酸-3-磷酸酯 (-)-3-去氢莽草酸苯甲酸 3-氨基苯甲酸乙酯苯酚 3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid