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齐墩果酸

齐墩果酸

CAS号：508-02-1

英文名：oleanolic acid

分子式

C30H48O3

熔点

>300°C(lit.)

密度

1.1 g/cm3

分子量

456.7

沸点

553.5ºC at 760 mmHg

溶解度

信号词

危险品标志

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化合物简介

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

基本信息

中文名称

齐墩果酸

英文名称

oleanolic acid

中文别名

齐墩果酸水合物、土当归酸、石竹素、土当归酸水合物

英文别名

oleanoic acid、Olean-12-en-28-oic acid, 3-hydroxy-, (3β)-、CARYOPHYLLIN、Oleanic acid、3-beta-Hydroxyolean-12-en-28-oic acid、Oleanolicacid、Taraligenin、Guagenin、Araligenin、Oleanolic Acid Hydrate、MoMorgenin、Taragenin、Oleanol、Gledigeni、Oleanolic、Oleanolic Acid、Oleanic Acid

CAS号

508-02-1

分子式

C30H48O3

分子量

456.7

精确质量

456.36

PSA

57.53

LOGP

7.2336

编号系统

UNII

6SMK8R7TGJ

物化性质

外观与性状

淡黄色

密度

1.1 g/cm3

沸点

553.5ºC at 760 mmHg

熔点

>300°C(lit.)

闪点

302.6ºC

折射率

1.557

稳定性

Stable at normal temperatures and pressures.

储存条件

2-8ºC

安全信息

RTECS号

RK0177965

安全说明

S26-S36

危险类别码

R36/37/38

WGK Germany

2

海关编码

2918199090

危险品标志

Xi

生产方法及用途

生产方法

1 醇提法将木根皮100g切成小块或丝状,加500ml 70%乙醇回流提取3次,每次约3h,醇提取液合并;然后蒸馏回收大部分乙醇,再加入硫酸使其浓度为15%,回流2h,放冷后过滤,滤饼用水洗3次,再用3% NaOH液煮沸2次,用水煮沸1次,每次沸腾后过滤,可得灰白色钠盐粗品。将粗品加约8倍量85%以上乙醇,0.5%活性炭,回流40min,过滤,滤液用HCl调至pH=3～4,放置过夜,过滤,滤饼用蒸馏水洗至无氯离子,干燥即得齐墩果酸精品。
2 水提取法取木根皮块粉碎后,用水煎煮3次,每次约1h,合并水煎液,浓缩成稀膏状。然后加入浓硫酸不断搅拌,使其浓度达到20%,加热约1h,放冷后加水稀释,过滤,滤饼水洗后,用3%NaOH溶液煮沸2次,水煮沸1次,每次沸腾后过滤,得钠盐粗品。将粗品加约8倍量85%以上乙醇,0.5%活性炭,回流40min,过滤,滤液再用HCl调至pH=3～4,放置过夜,过滤,滤饼用蒸馏水洗至无氯离子,干燥即得本品。

用途

齐墩果酸为广谱抗菌药，临床上用于护肝降酶，治疗支气管炎、肺炎、急性扁桃体炎、牙周炎、菌痢、急性肠胃炎、泌尿系统感染。另外，临床上还用于治疗急性肝炎。

合成路线

共找到33条合成路线 >

oleanolic acid 3-O-<O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)>-α-L-arabinopyranoside

oleanolic acid 3-O-<O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)>-α-L-arabinopyranoside

L-(+)-鼠李糖

L-(+)-鼠李糖

alpha-L-阿拉伯吡喃糖

alpha-L-阿拉伯吡喃糖

D-核糖

齐墩果酸

上游原料

共找到81个上游原料 >

3β-[(5S)-5-methoxycarbonyl-O4-(O4-α-L-rhamnopyranosyl-β-D-glucopyranosyl)-β-D-xylopyranosyloxy]-olean-12-en-28-oic acid β-D-galactopyranosyl ester

3β-[(5S)-5-methoxycarbonyl-O4-(O4-α-L-rhamnopyranosyl-β-D-glucopyranosyl)-β-D-xylopyranosyloxy]-olean-12-en-28-oic acid β-D-galactopyranosyl ester

Mimonoside A

齐墩果酸 beta-D-吡喃葡萄糖基酯

齐墩果酸 beta-D-吡喃葡萄糖基酯

3β-[(O-β-D-ribopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-β-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester

3β-[(O-β-D-ribopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-β-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester

(3,4,6-tri-O-acetyl-2-deoxy-α-D-threo-hex-2-enopyranosyl)benzene

(3,4,6-tri-O-acetyl-2-deoxy-α-D-threo-hex-2-enopyranosyl)benzene

oleanolic acid

下游产品

共找到26个下游商品 >

3-Epimaslinic acid benzyl ester

3-Epimaslinic acid benzyl ester

齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯

齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯

(3beta)-3-羟基-2-(羟基亚氨基)齐墩果-12-烯-28-酸苯甲酯

(3beta)-3-羟基-2-(羟基亚氨基)齐墩果-12-烯-28-酸苯甲酯

山楂酸

高根二醇

3-氧代-12-烯-28-齐墩果酸

3-氧代-12-烯-28-齐墩果酸

上游原料

3β-[(5S)-5-methoxycarbonyl-O4-(O4-α-L-rhamnopyranosyl-β-D-glucopyranosyl)-β-D-xylopyranosyloxy]-olean-12-en-28-oic acid β-D-galactopyranosyl ester Mimonoside A 齐墩果酸 beta-D-吡喃葡萄糖基酯 3β-[(O-β-D-ribopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-β-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester (3,4,6-tri-O-acetyl-2-deoxy-α-D-threo-hex-2-enopyranosyl)benzene oleanolic acid 3α-acetoxy-olean-12-en-28-oic acid methyl ester 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ciwujianoside C3 3-(alpha-L-阿拉伯吡喃糖基氧基)-齐墩果-12-烯-28-酸 O-6-脱氧-alpha-L-甘露糖基-(1-4)-O-6-O-乙酰基-beta-D-吡喃葡萄糖基-(1-6)-beta-D-吡喃葡萄糖基酯 [(4aS,6aS,6bR,8aR,10S,12aS,12bR)-10-(tert-Butyl-dimethyl-silanyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-hexadecahydro-2H-picen-4a-yl]-methanol [(3beta)-17-羧基-28-去甲齐墩果-12-烯-3-基]3-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡糖苷酸熊果酸 (4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13-octadecahydro-4a,14b-methanopicen-10-yl benzoate parkioside B (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-((tert-butyldimethylsilyl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid 3β-benzoyloxy-28-nor-oleana-12,17-diene oleanolic acid 3-O-β-D-glucosiduronic acid Mimonoside B oleanolic acid 3-O-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 3β-[(O-β-D-ribopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-[O-β-D-glucopyranosyl-(1->4)]-α-(L-arabinopyranosyl)oxy)]olean-12-en-28-oic acid O-β-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester 3-O-[α-L-arabinopyranosyl(1->2)-β-D-glucuronopyranosyl] oleanolic acid oleanolic acid 3-O-<O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)>-α-L-arabinopyranoside 银莲花甙 3-O-{[β-D-glucopyranosyl (1->2)]-[α-L-arabinopyranosyl (1->3)]-β-D-glucuronopyranosyl}oleanolic acid tert-butyl(((4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13-octadecahydro-4a,14b-methanopicen-10-yl)oxy)dimethylsilane 18,28-cyclo-olean-12-en-3β-ol salsoloside E copteroside E ciwujianoside C4 [(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(tert-Butyl-dimethyl-silanyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picen-4a-yl]-methanol parkioside A 12α-bromo-3β,13β-dihydroxyolean-28-oic acid γ-lactone sodium β-D-glucopyranosyl 3-[(O-β-D-glucopyranosyl-(1->3)-2-O-sulfo-α-L-arabinopyranosyl)oxy]olean-12-en-28-oate ((4aS,6aS,6bR,8aR,10S,12aS,12bR)-10-((tert-butyldimethylsilyl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-hexadecahydropicen-4a(2H)-yl)methyl benzoate sodium β-D-glucopyranosyl 3-[(O-(4-O-sulfo-β-D-glucopyranosyl)-(1->3)-α-L-arabinopyranosyl)oxy]olean-12-en-28-oate 3-beta-羟基齐墩果酸苯甲酸酯 stauntoside C1 mateglycoside A 3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[β-D-glucopyranosyl-(1->2)-β-D-galactopyranosyl] ester oleanolic acid 3-O-β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 地肤子皂苷 II (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3S,5R)-5-hydroxy-4-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid thalicoside B permethylate oleanolic acid 3-O-α-L-rhamnopyranosyl(1->4)-O-β-D-glucuronopyranoside

下游产品

3-Epimaslinic acid benzyl ester 齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯 (3beta)-3-羟基-2-(羟基亚氨基)齐墩果-12-烯-28-酸苯甲酯山楂酸高根二醇 3-氧代-12-烯-28-齐墩果酸 2,9-二甲基苉 2-氰基-3,12-二氧代齐墩果-1,9(11)-二烯-28-酸甲酯 2-羟基亚氨基-3-氧代齐墩果烷-12-烯-28-酸苯甲酯 1,2,5,6-四甲基萘 Methyl (3α,5ξ,18α)-3-hydroxy-12-oxoolean-9(11)-en-28-oate 3,12-二氧代齐墩果-9(11)-烯-28-酸甲酯 1,2,3,4-四甲基苯齐墩果酸苄酯齐墩果酸溴乙酯齐墩果酸乙酯 (4aS,6aR,6aR,6bR,8aR,12aS,14aR,14bS)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicene 2-(羟基亚氨基)-3-氧代-12-烯-28-齐墩果酸 12-烯并[2,3-c][1,2,5]氧二氮茂-28-齐墩果酸 1,2,7-Trimethylnaphthalene 齐墩果酸甲酯齐墩果酸二甲胺基乙酯 (4aS)-2,2,6a,6b,9,9,12a-heptamethyl-(6at,6bc,8at,12ac,12bt)-Δ10-hexadecahydro-14ac,4ar-oxaethano-picen-16-one 2,7-二甲基萘 Methyl (3β,5ξ,9ξ,18α)-3-acetoxy-12-oxooleanan-28-oate