Progesterone, 99%, reference material 孕-4-烯-3,20二酮

CAS 57-83-0 MFCD00003658

化学结构图

57-83-0
SMILES: CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

化学属性

Mol. FormulaC21H30O2
Mol. Weight314
Melting Point126-132
Solubility<0.1 G/100 ML AT 19 ºC
Density1.08
Stability对光敏感
Appearance 白色粉末状固体 powder
Refractive index182 ° (C=2, Dioxane)

别名和识别编码

Chemical NameProgesterone, 99%, reference material
CAS Number57-83-0
Synonym 4-​Pregnene-​3,20-​dione
MDL NumberMFCD00003658
PubChem Substance ID5994
Beilstein Registry Number1915950
EC Number200-350-6
Merck Number7773
Reaxys-RN1915950
Chemical Name Translation孕-4-烯-3,20二酮
Wiswesser Line NotationL E5 B666 OV MUTJ A1 E1 FV1
LabNetwork Molecule IDLN00235957
InChIInChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
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分类

  • {SNA} Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks,
  • {SNA} Abbott,
  • {SNA} Abbott, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Cell Signaling Enzymes, Cytokines, Growth Factors and Hormones, Fluorination Ready Pharma-Developed Compounds, Hormones, Lipid, PI-PZ, Progesterone, Progesterone Modulators, Steroid Hormones, Xenobiotics And Drug Metabolism Substrates, Xenobiotics and Drug Metabolism, 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, 生物活性小分子, 癌症研究,

产品应用

  • 诱发子宫内壁的成熟和分泌活性；抑制排卵。黄体酮和乳腺癌的发生有密切关系。

相关文献及参考

  • [2]. Zava DT, et al. Estrogen and progestin bioactivity of foods, herbs, and spices. Proc Soc Exp Biol Med. 1998 Mar;217(3):369-78.
  • [3]. Komesaroff PA, et al. Effects of wild yam extract on menopausal symptoms, lipids and sex hormones in healthy menopausal women. Climacteric. 2001 Jun;4(2):144-50.
  • [4]. Girling JE, et al. Progesterone, but not estrogen, stimulates vessel maturation in the mouse endometrium. Endocrinology. 2007 Nov;148(11):5433-41. Epub 2007 Aug 9.
  • Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2003),
  • Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002),
  • Gobert, R.P., et al., Convergent Functional Genomics Of Oligodendrocyte Differentiation Identifies Multiple Autoinhibitory Signaling Circuits. Mol. Cell. Biol. 29 , 1538-53, (2009) 摘要
  • Kapfhammer, J.P., et al., The detection and quantification of growth cone collapsing activities. Nat. Protoc. 2 , 2005-11, (2007) 摘要
  • Lanari, C., et al.: Breast Cancer

安全信息

RTECSTW0175000
GHS Symbol
Precautionary statements
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P318
  • P203
  • 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。
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
  • H350 May cause cancer 可能致癌
  • H351 Suspected of causing cancer 怀疑致癌
  • 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
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H362 May cause harm to breast-fed children 可能对母乳喂养的婴儿造成伤害
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Hazard Codes Xn
WGK Germany3
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Signal word Warning
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Risk Statements
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Implant
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 14 gm/kg/77W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Tumorigenic - increased incidence of tumors in susceptible strains
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 212,686,1966

{haz

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Parenteral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1289 mg/kg/78W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Reproductive - Tumorigenic effects - ovarian tumors
   Reproductive - Tumorigenic effects - uterine tumors
REFERENCE :
   PMDFA9 Pakistan Medical Forum.  (Karachi, Pakistan) V.1-8, 1966-73(?)  Disc
   ontinued.  Volume(issue)/page/year: 7,2

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Implant
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1296 mg/kg/77W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Tumorigenic - increased incidence of tumors in susceptible strains
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 212,686,1966

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 9500 mg/kg/19W-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   BJCAAI British Journal of Cancer.  (Macmillan Press Ltd., Houndmills,
   Basingstoke, Hants. RG21 2XS, UK)  V.1-    1947-  Volume(issue)/page/year:
   19,824,1965

TYPE OF TEST

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 327 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,1183,1995

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - ataxia
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   JMCMAR Journal of Medicinal Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC
   20037)  V.6-    1963-  Volume(issue)/page/year: 11,117,1968

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 200 mg/kg
REFERENCE :
   JOENAK Journal of Endocrinology.  (Biochemical Soc. Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1939-
   Volume(issue)/page

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - rat Embryo
DOSE/DURATION           : 2600 ug/L
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 67,1303,1981

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - hamster Embryo
DOSE/DURATION           : 30 mg/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 16,1329,1995

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Fibroblast
DOSE/DURATION           : 80 ug/L
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 67,1303,1981

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Human Kidney
DOSE/DURATION           : 100 ug/L
REFERENCE :
   CNJGA8 Canadian Journal of Genetics and Cytology.  (National Research
   Council of Canada, Publication Sales and Distribution, Ottawa ON K1A OR6,
   Canada)  V.1-    1959-  Volume(issue)/page/year: 10,299,1968

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraarterial
TEST SYSTEM             : Mammal - dog
DOSE/DURATION           : 100 ug/kg
REFERENCE :
   NATUAS Nature.  (Nature Subscript

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 100 mg/kg
SEX/DURATION            : female 20 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
   FESTAS Fertility and Sterility.  (American Fertility Soc., 608 13th Ave. S,
   Birmingham, AL 35282) V.1-    1950-  Volume(issue)/page/year: 16,158,1965

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 120 mg/kg
SEX/DURATION            : female 20 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - menstrual cycle changes or disorders
   Reproductive - Fertility - female fertility index (e.g. # females pregnant
   per # sperm positive females; # females pregnant per # females mated)
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   ACEDAB Acta Endocrinologica, Supplementum (Copenhagen).  (Periodica,
   Skolegade 12 E, DK-2500 Valby, Denmark)  No.1-    1948-
   Volume(issue)/page/year: 28,18,1956

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 25 mg/kg
SEX/DURATION            : female 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - mating performance (e.g. # sperm positive females
   per # females mated; # copulations per # estrus cycles)
REFERENCE :
   FESTAS Fertility and Sterility.  (American Fertility Soc., 608 13th Ave. S,
   Birmingham, AL 35282) V.1-    1950-  Volume(issue)/page/year: 5,282,1954

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 113 mg/kg
SEX/DURATION            : femal

其他信息

  • 孕酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/0
  • 测定方法:在40年代，只能用化学方法测定24h尿中孕酮的代谢产物孕二醇的排泄量，以反映孕酮分泌水平。 50年代开始采用生物法、化学法和气相层析法等测定血浆孕酮水平。 60年代末，开始应用放射性核素和蛋白竞争法。 70年代先后又出现了放射免疫分析法和放射受体法，大大提高了测定的灵敏度和精确度。血孕酮测定已广泛应用，尿孕二醇的测定已失去重要性。尿正常值卵泡期1mg/24h，黄体期2～8mg/24h。育龄期妇女孕酮水平的变化，可反映月经周期中不同阶段。妊娠妇女，血孕酮持续上升，失去正常的周期性。在先天性17α-羟化酶缺乏症中，孕酮与17α-羟孕酮之间的比率关系失常，孕酮上升，而17α-羟孕酮则降低。
  • 方法二:由妊烯醇酮氧化得到。将干燥的甲苯加入干燥的反应锅内，加入环已酮及妊烯醇酮，搅拌溶解，蒸甲苯脱水至尽，迅速加入异丙醇铝，于115℃氧化反应2h，冷却至80℃左右，在搅拌下加入5%稀硫酸，静置分层，分去水层，甲苯层用水洗至中性后进行水蒸气蒸馏，蒸出甲苯及环已酮。冷却，过滤，滤渣用石油醚搅成浆状，过滤，以石油醚洗涤，干燥得黄体酮粗品。粗品溶于乙醇，用活性炭脱色，重结晶成品，收率80%。
  • 用途一:属甾体激素、孕激素类药
  • {Chemic
  • 孕激素:孕酮是由卵巢黄体细胞分泌的一种含有21个碳原子的类固醇激素，也是合成一切类固醇激素的中间产物，属于孕激素之一。有两种晶型，即α-型和β-型，两种晶型有相同的生理活性，α-型是从稀乙醇中析出，为正交晶系白色棱柱状结晶，β-型为正交晶系白色针状结晶，二者均不溶于水，溶于乙醇、乙醚、氯仿、丙酮、二氧六环及浓硫酸。 孕酮是由卵巢、胎盘及肾上腺皮质分泌的。其生理功能主要表现为使经过雌激素的作用已处于增生状态的子宫内膜继续发育、增生、增厚，肥大、松软和分泌粘液，为受精卵的着床准备好有利条件。受精卵着床后，早期的生存发育，也直接处在高涨的孕酮分泌控制影响下。因此，孕酮既是雌性生殖系统中极重要的激素，又是甾体类激素生物合成途径中的重要中间产物。所有分泌甾体激素的腺体，都能合成孕酮，但作为主要激素而向腺外分泌，则只限于卵巢和胎盘。卵巢大量分泌孕酮，是在排卵后的黄体期，分泌的组织是颗粒黄体细胞，所以孕酮又称黄体酮。黄体萎缩后，孕酮分泌也低落。正常妇女在妊娠8～9周之后，胎盘就成为分泌孕酮的主要器官，但卵巢也仍能继续分泌，直到妊娠结束为止。 孕酮的主要生理功能： 1、维持雌性动物的妊娠，并导致妊娠动物出现一系列的生理变化， 如抑制母畜发情。 2、促进子宫粘膜层增厚、腺体的弯曲度以及分泌机能的增加。 3、抑制子宫的蠕动，并使子宫颈收缩，分泌粘稠液体等。这些生理变化为早期胚胎的运行、生长发育、附植以及附植后胎儿的继续生长提供适宜的环境条件。 4、少量孕激素与雌激素协同，促进母畜发情。孕激素与催乳素协同，可促进乳腺腺体的发育。 5、孕激素参与下丘脑和垂体前叶的反馈调节， 使动物生殖激素的分泌协调平衡。体内含量，各种家畜卵泡期孕酮含量低于1毫微克/毫升，牛在黄体期约4毫微克/毫升，妊娠期约18毫微克/毫升。
  • 参考质量标准:含量≥98%
  • {Che
  • 用途四:诱发子宫内壁的成熟和分泌活性；抑制排卵。黄体酮和乳腺癌的发生有密切关系。
  • 上游原料:环己酮 --> 稀硫酸 --> 醋酸妊娠双烯醇酮酯 --> 异丙醇铝 --> 孕烯醇酮
  • 属黄体（the corpus luteum）产生的类固醇激素。不溶于水，溶于醇、丙酮、二恶烷和浓硫酸。
  • 比旋光度:186 ° (c=1, ethanol)
  • MSDS 信息:4-Pregnene-3,20-dione(57-83-0).msds
  • 参考质量标准:含量≥98%；mp128-131℃；比旋光度[α] 20 D +186°-+198°；检测澄清度试验、干燥失重及灼烧残渣等杂质含量。
  • 下游产品:醋酸去氧皮质酮 --> 16alpha-甲基-11beta,17alpha,21-三羟基-9alpha-氟孕甾-1,4-二烯-3,20-二酮-21-醋酸酯 --> 9Α-溴-16Β-甲基孕甾-1,4-二烯-11Β,17Α,21-三醇-3,20-二酮-21-醋酸酯 --> 16Α,17Α-环氧孕甾-5,9(11

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Sterol Lipids - Lipids
  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. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Building Blocks 手性分子砌块
  4. Complex Molecules - Chiral Building Blocks
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Market Segments - Analytical Standards
  4. Standards for Pharma Clinical Forensic &amp; Veterinary Analysis - Market Segments
  5. Neats and Solutions - Standards for Pharma Clinical Forensic &amp; Veterinary Analysis
  6. Hormones - Neats and Solutions
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Pharmaceutical Standards - Chromatography
  5. Pharmaceutical Secondary Standards - Pharmaceutical Standards
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Cytokines, Growth Factors and Hormones - Cell Signaling and Neuroscience
  5. Hormones - Cytokines, Growth Factors and Hormones
  6. Steroid Hormones - Hormones
  7. Progesterone - Steroid Hormones
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Steroids
  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. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Xenobiotics and Drug Metabolism
  6. Inhibitors
  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. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Cytokines, Growth Factors and Hormones
  5. Hormones
  6. Steroid Hormones
  7. Other Steroid Products
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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