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前列腺素e

前列腺素e

CAS号：363-24-6
英文名：prostaglandin E2
分子式
C20H32O5
熔点
66-68 °C
密度
1.148 g/cm3
分子量
352.465
沸点
530.071ºC at 760 mmHg
溶解度
insoluble
信号词
Danger
危险品标志
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化合物简介
The most common and biologically potent of mammalian prostaglandins. Oxytocic; abortifacient.
基本信息
中文名称
前列腺素e
英文名称
prostaglandin E2
中文别名
前列腺素E、(5Z,11Α,13E,15S)-11,15-二羟基-9-酮前列-5,13-二烯-1-酸、前列腺素E2、地诺前列酮
英文别名
PGE2、Cerviprost、(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid、ProstaglandinE2、prostin、Prostaglandin E2、Dinoprostone、Propess、Prepidil、MCH (human,mouse,rat)、Cervidil、prostine2、Prostenon、l-pge2、Cervidil(R)
CAS号
363-24-6
分子式
C20H32O5
分子量
352.465
精确质量
352.225
PSA
94.83
LOGP
3.2511
编号系统
UNII
K7Q1JQR04M
物化性质
外观与性状
白色晶体
密度
1.148 g/cm3
沸点
530.071ºC at 760 mmHg
熔点
66-68 °C
闪点
288.452ºC
水溶解性
insoluble
稳定性
Stable under normal temperatures and pressures. Light sensitive.
储存条件
-20ºC
蒸汽压
0mmHg at 25°C
安全信息
RTECS号
UK8000000
安全说明
S53-S22-S26-S36/37/39
危险类别码
R60; R22
WGK Germany
3
危险品标志
T
危险标志
GHS07, GHS08
信号词
Danger
危险性防范说明
P201; P308 + P313
危险性描述
H302; H360
生产方法及用途
生产方法
以羊精囊为原料 反应液的制备 取-30℃冷藏的羊精囊,除去结缔组织及脂肪,每1kg加1L 0.154mol/L氯化钾溶液,在4000r/min下离心25min,取上清液,过滤,得清液。残渣加氯化钾再提取一次,离心过滤后,合并二次上清液。加2mol/L枸橼酸调pH5,在4000r/min下离心25min,弃上清液,加10
0 ml 0.2mol/L磷酸盐缓冲液洗下沉淀,再加100ml 6.2.5×10-
5 mol/L EDTA溶液搅匀,加2mol/L氢氧化钾调pH8,得酶混悬液。取酶的混悬液,每升加氢醌40mg、加GSH 500mg,先用少量水溶解后,加入酶的混悬液中,再将1kg羊精囊加1g AA,搅拌通氧,升温至37-38℃,孵育1h,得反应液。 绵羊精囊[pH8]→[KCl, EDTA Na2]酶混悬液[氢醌,谷胱甘肽]→[花生四烯酸,O2]反应液 PGE粗品的制备 将反应液加丙酮(第一次3倍量,第二次2倍量)提取两次,每次0.5-1h,过滤,合并两次滤液,45℃减压浓缩或薄膜浓缩,得浓缩液。加4mol/L盐酸调pH 3,加乙醚、0.2mol/L磷酸盐缓冲液、石油醚分别萃取3次,取水层,加4mol/L盐酸调pH 3,加二氯甲烷萃取3次,二氯甲烷层经水洗、无水硫酸钠脱水后,密塞置冰箱中过夜,过滤,40℃以下减压浓缩得黄色油状物,即PGS粗品。每1g PGS粗品用15g 100-160目活化硅胶,湿法装柱。将PGS粗品溶解于少量氯仿,过柱层析分离,依次以氯仿、V氯仿:V甲醇氯仿:V甲醇反应液[丙酮,乙醚,二氯甲烷]→PGS粗品[硅胶柱]→PGE粗品 APGE2成品的制备 每1g PGE粗品用20g硅胶,取200-250目10倍PGE质量的活化硝酸银硅胶混悬于V乙酸乙酯:V冰醋酸:V石油醚:V水1和PGE2部分。将PGE2部分于35℃以下充氮浓缩至无醋酸味,加乙酸乙酯溶解,加水洗酸,pH4-5,加生理盐水除银。乙酸乙酯溶液加无水硫酸钠干燥,充氮,密塞,置冰箱过夜,过滤,滤液于35℃以下充氮浓缩,得PGE2精晶,经乙酸乙酯-己烷重结晶2次,得PGE2成品。 PGE粗品[硝酸银硅胶柱]→PGE2(油)[乙酸乙酯-己烷]→PGE2。
用途
1.子宫兴奋药。用于妊娠催产、中期妊娠引产和治疗性流产、术前宫颈扩张。少数病例可有寒战、呕吐、轻度腹泻,一般短时间内可自行缓解,或经对症处理后很易控制。静滴时有类似静脉炎症状,停药后自行消失。用药过程中严密观察宫缩情况,随时调整给药剂量,以防宫缩过强而发生子宫破裂。
合成路线
共找到3条合成路线 >
花生四烯酸
506-32-1
花生四烯酸
凝血烷
54397-85-2
凝血烷
前列腺素e
363-24-6
前列腺素e
12(S)-HYDROXY-(5Z,8Z,10E,14Z)-EICOSATETRAENOIC ACID
54397-83-0
12(S)-HYDROXY-(5Z,8Z,10E,14Z)-EICOSATETRAENOIC ACID
上游原料
共找到38个上游原料 >
(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid
77494-48-5
(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid
PROSTAGLANDINS E2 METHYL ESTER
31753-17-0
PROSTAGLANDINS E2 METHYL ESTER
Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoate
77494-47-4
Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoate
(+)-(3a'S,3''S,5'R,6'R,6a'S)-methyl (5Z)-7-<6'<(1''E)-3''-<(tert-butyldimethylsilyl)oxy>-1''-octenyl>-2',2'-dimethyl-3a',5',6',6'-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-yl>-5-heptenoate
103904-98-9
(+)-(3a'S,3''S,5'R,6'R,6a'S)-methyl (5Z)-7-<6'<(1''E)-3''-<(tert-butyldimethylsilyl)oxy>-1''-octenyl>-2',2'-dimethyl-3a',5',6',6'-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-yl>-5-heptenoate
Cis-3,5-二乙酰氧基-1-环戊烯
54664-61-8
Cis-3,5-二乙酰氧基-1-环戊烯
meso-4β,6-diacetoxy-2,2-dimethyl-3αβ,5,6α,6αβ-tetrahydro-4H-cyclopenta-1,3-dioxole
103904-95-6
meso-4β,6-diacetoxy-2,2-dimethyl-3αβ,5,6α,6αβ-tetrahydro-4H-cyclopenta-1,3-dioxole
下游产品
共找到4个下游商品 >
同分异构体(物),同质异能素
4510-16-1
同分异构体(物),同质异能素
前列腺素
551-11-1
前列腺素
(5Z,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,9,13-trien-1-al
62410-93-9
(5Z,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,9,13-trien-1-al
前列腺素A2
13345-50-1
前列腺素A2
上游原料
(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid PROSTAGLANDINS E2 METHYL ESTER Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (+)-(3a'S,3''S,5'R,6'R,6a'S)-methyl (5Z)-7-<6'<(1''E)-3''-<(tert-butyldimethylsilyl)oxy>-1''-octenyl>-2',2'-dimethyl-3a',5',6',6'-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-yl>-5-heptenoate Cis-3,5-二乙酰氧基-1-环戊烯 meso-4β,6-diacetoxy-2,2-dimethyl-3αβ,5,6α,6αβ-tetrahydro-4H-cyclopenta-1,3-dioxole Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-[[carbo(2',2',2'-trichloroethoxy)]methylamino]-8-(phenylsulfonyl)-5,13-prostadienoate (+)-(3As,6as)-3a,6a-二氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮 (-)-(3a'S,3''S,5'R,6'R,6a'S)-methyl (5Z)-7-[6'[(1''E)-3''-hydroxy-1''-octenyl]-2',2'-dimethyl-3a',5',6',6a'-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-yl]-5-heptenoate methyl 7-[1-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-(dimethylamino)cyclopentyl]hept-5-enoate (E)-(1α,2α,3β,5α)-2-[3-(dimethyl-t-butylsiloxy)oct-1-enyl]spiro[bicyclo[3.2.0]heptane-6,2'-[1,3]dioxolan]-3-ol PGE2 11,15-bis-t-butyldimethylsilyl ether 花生四烯酸 环戊二烯 (Z)-7-((1S,2S,3R,E)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-(hydroxyimino)-1-(phenylsulfonyl)cyclopentyl)hept-5-enoic acid Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate methoxime methyl ester of PGE2 bis t-butyldimethylsilyl ether (3AR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one Phenylacetyl-triphenylsilan (1E,3S)-3-t-butyldimethylsilyloxy-1-lithio-octane (Z)-7-((1S,2S,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-((2-hydroxy-2-methylpropyl)amino)-1-(phenylsulfonyl)cyclopentyl)hept-5-enoic acid (-)-(3S)-3-(O-tert-butyldimethylsilyl)-1-octyne (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid methyl 7-iodohept-5-enoate 前列腺素 H2 Bis(tert-butyldimethylsilyl)-PGE2 oxime (1R,4R,5S,7R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-bicyclo[2.2.1]heptan-2-one (3αS,4R,6S,6αR)-4β-acetoxy-2,2-dimethyl-6-hydroxy-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxole methyl (Z)-7-((1S,2S,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-(methyl((2,2,2-trichloroethoxy)carbonyl)amino)-1-(phenylsulfonyl)cyclopentyl)hept-5-enoate (S)-1-辛炔-3-醇 methyl (Z)-7-((1S,2S,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-(methylamino)-1-(phenylsulfonyl)cyclopentyl)hept-5-enoate (Z)-7-((1S,2S,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-(methylamino)-1-(phenylsulfonyl)cyclopentyl)hept-5-enoic acid (5Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-(methoxyimino)cyclopentyl)hept-5-enoic acid 3-phenyl-2H,6H-[1,3,4]thiadiazino[2,3-b]quinazolin-6-one (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one (1R,5R,6S,8R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-2-oxa-bicyclo[3.2.1]octan-3-one (2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-2-(6-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)hex-2-yn-1-yl)cyclopentanone O-methyl oxime
下游产品
同分异构体(物),同质异能素 前列腺素 (5Z,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,9,13-trien-1-al 前列腺素A2
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