(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

  1. Life Science 生命科学
  2. Cancer Research
  3. Tumor Growth Regulation - Cancer Research
  4. Tumor Promotors - Tumor Growth Regulation
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. P - Bioactive Small Molecules
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Fatty Acyls - Lipids
  5. Eicosanoids (Prostaglandins, Leukotrienes) - Fatty Acyls
  6. Prostaglandins - Eicosanoids (Prostaglandins, Leukotrienes)
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Fatty Acyls - Lipids
  5. Eicosanoids (Prostaglandins, Leukotrienes) - Fatty Acyls
  6. Prostaglandins - Eicosanoids (Prostaglandins, Leukotrienes)
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Libraries
  5. Carbohydrate Library
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Libraries
  6. Carbohydrate Library
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Leukotrienes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Fatty Acids
  5. Enzyme Substrate
  6. Chromogen
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Leukotrienes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Cofactor
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Pathways
  6. Metabolites and Cofactors on the Metabolic Pathways Chart
  7. Cholesterol
  1. Medical Research Areas
  2. GPCR & G Protein
  3. Prostaglandin Receptor  (前列腺素受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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