(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-Hydroxyoct-1-En-1-Yl)-5-Oxocyclopentyl)Hept-5-Enoic Acid (Z)-7-((1R,2R,3R)-3-羟基-2-((S,E)-3-羟基-1-烯-1-基)-5-氧代环戊基)庚-5-烯酸

CAS 363-24-6 MFCD00077861

化学结构图

363-24-6
SMILES: CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(=O)O

化学属性

Mol. FormulaC20H32O5
Mol. Weight352.47
Melting Point66-68°C
Solubility不溶
Appearance 2α 本品为白色至类白色的固体。Mp 64-66℃,比旋度-61°(26℃, c=1, THF)。在pH<;4 或 pH>;8时易水解。易溶于氯仿、醋酸乙酯、甲醇、无水乙醇等有机溶剂,微溶于水。 前列腺素对晚期妊娠引产,国外于1968年开始研究并相继应用于临床。 PGE powder 对各期妊娠子宫均有收缩作用,以妊娠晚期最为敏感。PGE 所引起的子宫收缩频率、强度、持续时间均与正常分娩相似。最常用的方法有:静脉滴注、舌下或口服、阴道内给药等。 2 、PGF 、 PGF
Boiling Point530.1°C at 760 mmHg

别名和识别编码

Chemical Name(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-Hydroxyoct-1-En-1-Yl)-5-Oxocyclopentyl)Hept-5-Enoic Acid
CAS Number363-24-6
Synonym ######## (15s)-prostaglandine2 (5Z,11-alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid (5Z,11A,13E,15S)-11,15-DIHYDROXY-9-OXO-PROSTA-5,13-DIEN-1OIC ACID (5Z,11Α,13E,15S)-11,15-二羟基-9-酮前列-5,13-二烯-1-酸 (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid Dinoprostone PGE2 (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid Dinoprostone PGE2 Prostaglandin E2 (5z,11-alpha,13e,15s)-11,15-dihydroxy-9-oxo-prosta-13-dien-1-oicacid 11,15-dihydroxy-9-oxo-,(5z,11-alpha,13e,15s)-prosta-13-dien-1-oicacid 5 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicaci 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid 7-[3-羟基-2-(3-羟基-1-辛烯基)-5-氧代
Reaxys-RN2224724
PubChem Substance ID125307563
MDL NumberMFCD00077861
Merck Number7877
EC Number206-656-6
Beilstein Registry Number4709356
Chemical Name Translation(Z)-7-((1R,2R,3R)-3-羟基-2-((S,E)-3-羟基-1-烯-1-基)-5-氧代环戊基)庚-5-烯酸
Wiswesser Line NotationL5VTJ B2U4VQ C1U1YQ5 DQ
LabNetwork Molecule IDLN00190301
InChIInChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
Canonical SMILESCCCCC[C@H](O)/C=C/[C@@H]1[C@H](C(C[C@H]1O)=O)C/C=C\CCCC(O)=O
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分类

  • {SNA} Eicosanoids (Prostaglandins, Leukotrienes), Fatty Acyls, Miscellaneous Reagents and Supplements, Prostaglandins, 生化试剂, 细胞培养, 脂类, 试剂和添加剂
  • {SNA} Allium sativum (Garlic), Arachidonic Acid Cascade, Eicosanoids (Prostaglandins, Leukotrienes), Fatty Acyls, Lipid, Lipid Library Collection, Lipids in Cell Signaling, Metabolite Libraries and Collections, Phytochemicals by Plant (Food/Spice/Herb), Prostaglandins, Tumor Promotors, 代谢组学, 代谢通路, 代谢通路图中的代谢产物和辅酶分子, 生化试剂, 癌症研究,
  • {SNA} Allium sativum (Garlic),

产品应用

  • The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

相关文献及参考

  • [2]. Fernandez-Repollet E, et al. In vivo effects of prostaglandin E2 and arachidonic acid on phagocytosis of fluorescent methacrylate microbeads by rat peritoneal macrophages. J Histochem Cytochem. 1982 May;30(5):466-70.
  • [3]. Haylor J, et al. Renal vasodilator activity of prostaglandin E2 in the rat anaesthetized with pentobarbitone. Br J Pharmacol. 1982 May;76(1):131-7.
  • Bowolaksono, A., et al., Anti-Apoptotic Roles of Prostaglandin E2 and F2alpha in Bovine Luteal Steroidogenic Cells Biol. Reprod. 79 , 310-7, (2008) 摘要
  • Fosslein, E., Review: molecular pathology of cyclooxygenase-2 in cancer-induced angiogenesis. Ann. Clin. Lab. Sci. 31 , 325-348, (2001)
  • Hamberg, M., et al.: J. Biol. Chem., 246, 6713 (1971),
  • Krysan, K. et al., COX-2-dependent stabilization of survivin in non-small cell lung cancer. FASEB J. 18 , 206-208, (2004) 摘要
  • Radu, C.G., et al., Differential proton sensitivity of related G protein-coupled receptors T cell

安全信息

RTECSUK8000000
Storage condition -20 -20°C 储存温度-20°C
Signal word
Hazard statements
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H302 Harmful if swallowed 吞食有害
Precautionary statements
  • P308+P313
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P301+P312+P330
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P405 Store locked up. 上锁保管。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
GHS Symbol
WGK Germany3
Hazard Codes T
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 19700 ug/kg
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Skin and Appendages - dermatitis, other (after systemic exposure)
   Skin and Appendages - hair
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 8,787,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - hypermotility, diarrhea
   Skin and Appendages - hair
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Send

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 750 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - hypermotility, diarrhea
   Skin and Appendages - hair
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 8,787,1974

{hazard_co

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 23200 ug/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - hypermotility, diarrhea
   Skin and Appendages - hair
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 8,787,1974

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Intracerebral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 15 ug/kg
REFERENCE :
   REXMAS Research in Experimental Medicine.  (Springer-Verlag, Heidelberger
   Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.)  V.157-    1972-
   Volume(issue)/page/year: 186,1,1986

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 100 nmol/L
REFERENCE :
   JIDEAE Journal of Investigative Dermatology.  (Williams & Wilkins Co., 428
   E. Preston St., Baltimore, MD 21202)  V.1-    1938- Volume(issue)/page/year:
   66,313,1976

TYPE OF TEST            : Sperm Morphology
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 3 mg/kg
REFERENCE :
   INJFA3 International Journal of Fertility.  (Allen Press, 1041 New
   Hampshire,  St., Lawrence, KS 66044)  V.1-    1955- Volume(issue)/page/year:
   21,82,1976

TYPE OF TEST            : Unscheduled DNA synthesis
TEST SYSTEM             : Rodent - guinea pig Lung
DOSE/DURATION           : 1 mg/L
REFERENCE :
   PSEBAA Proceedings of the Society for Experimental Biology and Medicine.
   (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1903/04-
   Volume(issue)/page/year: 171,109,1982

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6 mg/kg
SEX/DURATION            : female 12-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - homeostasis
REFERENCE :
   PRGLBA Prostaglandins.  (Geron-X, Inc., P.O. Box 1108, Los Altos, CA 94022)
   V.1-    1972-  Volume(issue)/page/year: 3,299,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 75 mg/kg
SEX/DURATION            : female 6-10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - eye/ear
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   TOLED5 Toxicology Letters.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1977-  Volume(issue)/page/year: 1,3,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1200 ug/kg
SEX/DURATION            : female 9-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   AKGIAO Akushcherstvo i Ginekologiya (Moscow).  (V/O Mezhdunarodnaya Kniga,
   113095 Moscow, USSR) No.1-    1936-  Volume(issue)/page/year: 56(8),53,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 30 mg/kg
SEX/DURATION            : female 1-5 day(s) after conception
TOXIC EFFECTS

其他信息

  • 用途一: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。
  • 上游原料:氢 --> 氯化钾 --> 柠檬酸 --> 花生四烯酸 --> 磷酸盐缓冲液 --> 谷胱甘肽
  • 比旋光度:-85.5 ° (c=1, C2H5OH)
  • MOL 文件:363-24-6.mol
  • 下游产品:列腺素 E1
  • 地诺前列酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 P1884 前列腺素E2 Prostaglandin E2 1MG 581元 2014/06/02 P1884 前列腺素E2 Prostaglandin E2 10MG 4340元 2010/06/21 233560100 地诺前列酮 Prostaglandin E2 98% 10 MG 5169元
  • MSDS 信息:PGE2(363-24-6).msds
  • Sigma Aldrich:363-24-6(sigmaaldrich)
  • F:8-10
  • Acros Organics:前列腺素e Prostaglandin E2, 98%(363-24-6)
  • 方法一: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100 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 Na 2 ]酶混悬液[氢醌,谷胱甘肽]→[花生四烯酸,O 2 ]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 =98:2、 V 氯仿 :V 甲醇 =96:4三种溶液洗脱,收集洗脱液,硅胶柱层析鉴定,相同洗脱液合并,得PGA和PGE部分。将PGE洗脱液在35℃以下浓缩,得PGE粗品。 反应液[丙酮,乙醚,二氯甲烷]→PGS粗品[硅胶柱]→PGE粗品 APGE 2 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 =220:22.5:125:5(石油醚的bp 90-120℃)的展开剂中。湿法装柱,将粗品用少量的同一展开剂溶解,上柱,洗脱。分别收集PGE 1 和PGE 2 部分。将PGE 2 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PGE 2 精晶,经乙酸乙酯-己烷重结晶2次,得PGE 2 成品。 PGE粗品[硝酸银硅胶柱]→PGE 2 (油)[乙酸乙酯-己烷]→PGE 2 。

系列性分类


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