5-Pregnen-3β-ol-20-one 孕烯醇酮

CAS 145-13-1 MFCD00003628

化学结构图

145-13-1
SMILES: CC(=O)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C

化学属性

Mol. FormulaC21H32O2
Mol. Weight316
Density1.422
Melting Point187.0 to 192.0 deg-C
Appearance 白色结晶性粉末。熔点193℃。不溶于水。在下列物质中的溶解度（g/100ml）：四氯化碳0.5，石油醚0.1，乙酸乙酯1.1，丙酮0.6，氯仿17.0，乙醇1.9，苯0.9，异丙醇1.5，丙二醇0.1，二氧六环3.1，苄醇8.1。
SolubilitySoluble in ethanol (22 mg/ml at 25 °C), chloroform, and DMSO (22 mg/ml at 25 °C). Insoluble in water, , , DMSO 22 mg/mL Water <1 mg/mL Ethanol 22 mg/mL
pH:A

别名和识别编码

Chemical Name5-Pregnen-3β-ol-20-one
CAS Number145-13-1
Synonym Bina-Skin Arthenolone Pregnolon {uni_hamburg} Pregn-5-en-20-one, 3β-hydroxy- 3B-Hydroxy-5-pregnen-20-on prenolon Pregnenolone (progesterone precursor) 5-Pregnen-3b-ol-20-one 3-beta-hydroxy-pregn-5-en-20-on Pregn-5-en-20-one, 3-hydroxy-, (3β)- 1-((3S,8S,10R,13S,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone DELTA5-PREGNEN-3B-OL-20-ONE {Chemi 5-PREGNEN-3BETA-OL-20-ONE 1-((3S,8S,9S,10R,13S,14S,17S)-3-HYDROXY-10,13-DIMETHYL-2,3,4,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL)-ETHANONE Enelone 5-Pregnen-3β-ol-20-one 5-Pregnenolone; Pregnenolone; Pregnolon; Prenolon; 3b-Hydroxy-5-pregnen-20-one Pregneton 3-beta-Hydroxypregn-5-en-20-one Pregnenlolone 3β-Hydroxypregn-5-en-20-one 3β-Hydroxy-5-pregnen-20-one 1-((3S,8S,10R,13S,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone {Ch 妊娠烯醇酮 孕甾烯醇酮 3β-Hydroxy-5-pregnen-20-one Pregne 3-羟基-5-妊烯酮 妊烯醇酮 pregnenolone (INN) 孕烯醇酮 PREGNENOLONE Skinostelon Pregnetan 3β-Hydroxy-5-pregnen-20-on 孕烯 3BETA-HYDROXY-5-PREGNEN-20-ONE DELTA5-PREGNE 孕甾烯醇酮;3β-羟基孕甾-5-烯-20-酮 DELTA5-PREGNENOLONE 3b-hydroxy-5-pregnen-20-one 3β-Hydroxy-Δ5-pregnen-20-one 苯酮
EC Number205-647-4
Beilstein Registry Number8(3)949
MDL NumberMFCD00003628
PubChem Substance ID8955
Reaxys-RN2059026
Merck Number7733
Chemical Name Translation孕烯醇酮
LabNetwork Molecule IDLN00872904
InChIInChI=1S/C21H32O2/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/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
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分类

  • {SNA} Bioactive Small Molecules, Lipid, Lipid Library, Metabolic Libraries, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, P, Steroid Metabolism, 代谢组学, 细胞生物学
  • {SNA} Lipid, Lipid Library Collection, Metabolite Libraries and Collections, 代谢组学, 代谢通路, 代谢通路图中的代谢产物和辅酶分子, 固醇代谢, 细胞生物学
  • {SNA} Bioactive Small Molecules, Cell Biology, Lipid, Lipid Library, Metabolic Libraries, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart,
  • Steroids
  • Pharmaceuticals
  • {SNA} Lipid,

产品应用

  • An prohormone neurosteroid also a precursor to gonadal steroid hormones and the adrenal corticosteroids.

相关文献及参考

  • [2]. Ducharme N, et al. Brain distribution and behavioral effects of progesterone and pregnenolone after intranasal or intravenous administration. Eur J Pharmacol. 2010 Sep 1;641(2-3):128-34.
  • [3]. Alan Shiels. TRPM3_miR-204: a complex locus for eye development and disease. Hum Genomics. 2020 Feb 18;14(1):7.
  • Bjondahl, K., et al.: Med. Biol., 54, 454
  • Short: EINECS Title: EINECS (European Inventory of Existing Commercial Chemical Substances) Source: Official Journal of the European Communities Volume: C 146 A (15.06.1990) Page: 1 Year: 1990 Internet Resource: http://ecb.jrc.ec.europa.eu/esis/index.php?PGM=ein Publish_Date: 1990/06/15
  • Short: III/35E Title: Nuclear Magnetic Resonance (NMR) Data: Chemical Shifts for Oxygen-17 Author: Duddeck, H.; Toth, G.; Simon, A. Editor: Gupta, R.R.; Lechner, M.D. Source: Landolt-Börnstein, New Series Volume: III/35E Year: 2002 Keyword: Alipathic and Aromatic hydrocarbons; Coupling constant j; Nuclear

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • 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；
  • 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
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
RTECSTU5560700
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 储存温度-20°C 储存温度2-8℃ 
TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
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            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Parenteral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 35 mg/kg
SEX/DURATION            : female 7 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
   JEMEAV Journal of Experimental Medicine.  (Rockefeller Univ. Press, 1230
   York Ave., New York, NY 10021)  V.1-    1896-  Volume(issue)/page/year:
   102,347,1955

其他信息

  • 图谱信息:孕烯醇酮(145-13-1)核磁图( 13 CNMR) 孕烯醇酮(145-13-1)质谱(MS) 孕烯醇酮(145-13-1)红外图谱(IR2) 孕烯醇酮(145-13-1)红外图谱(IR1) 孕烯醇酮(145-13-1)Raman光谱 孕烯醇酮(145-13-1)核磁图( 1 HNMR)
  • Sigma Aldrich:145-13-1(sigmaaldrich)
  • 用途二:用于甾体类药物中间体和甾体类药物的合成
  • 用途一:用作医药黄体酮的中间体
  • 用途三:用于生化研究。激素类药黄体酮的中间体。
  • 上游原料:16-妊娠双烯醇酮
  • 比旋光度:28.5 ° (c=1, EtOH)
  • 下游产品:孕酮 --> 非那雄胺
  • 方法一:将乙酸妊娠双烯醇酮、乙醇、雷氏镍一起加热，50℃左右使全部溶解，然后抽真空通入氢气，反复3次后，在搅拌下通氢，在34-36℃反应3.5h。静置，通氮气排出氢气，滤出催化剂。将滤液浓缩回收大部分乙醇，析出结晶。将结晶投入水解锅内减压蒸尽乙醇，冷却后加入甲醇，加热回流使全部溶解，加入50%碳酸钾水溶液，回流1.5h，减压浓缩回收甲醇，出料后冷却至5℃以下，滤取结晶，用温水洗至中性，烘干。再用10倍量乙醇溶解，加活性炭脱色，重结晶1次，得妊烯醇酮。
  • Acros Organics:孕烯醇酮 Pregnenolone, 99%(145-13-1)
  • 孕烯醇酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 P0786 孕烯醇酮 Pregnenolone 25G 690元 2014/06/02 P0786 孕烯醇酮 Pregnenolone 5G 230元 2010/06/21 164421000 孕烯醇酮 Pregnenolone 99% 100 GR 3141元
  • TCI Shanghai:孕甾烯醇酮 Pregnenolone,>;98.0%(GC)(145-13-1)
  • Pregnenolone is an endogenous neurosteroid that is involved in the steroidogenesis of progesterone, glucocorticoids, mineralocorticoids, androgens, and estrogens, making it a prohormone. It has been observed to inhibit GABA-gated chloride currents by enhancing receptor desensitization. Pregnenolone is an inhibitor of GABA Receptor and an activator of PXR.
  • MOL 文件:145-13-1.mol

系列性分类

  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. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Libraries - Metabolomics
  4. Lipid Library - Metabolic Libraries
  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. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Aromatic Ketones
  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. 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. Cannabinoid Receptor  (大麻素受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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