(3S,9S,10R,13R,14R,17R)-10,13-Dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol (3S,9S,10R,13R,14R,17R)-10,13-二甲基-17-((R)-6-甲基庚-2-基)-2,3,4,9,10,11,12,13,14,15,16,17-十二氢-1H-环戊二烯[a]菲-3-醇

CAS 434-16-2 MFCD00003624

化学结构图

434-16-2
SMILES: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C

化学属性

Mol. FormulaC27H44O
Mol. Weight385
Melting Point148-152 °C(lit.)
TSCAYes
Solubility不溶
Appearance 片状结晶（甲醇水溶液/乙醚）。熔点150-151℃（无水物）。[α]20/D-113.6°（氯仿）。露置空气中易氧化。

别名和识别编码

Chemical Name(3S,9S,10R,13R,14R,17R)-10,13-Dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number434-16-2
Synonym (-)-7-DEHYDROCHOLESTEROL (-)-7-Dehydrocholesterol (-)-7-Dehydrocholesterol 3β-Hydroxy-5,7-cholestadiene 5,7-Cholestadien-3β-ol Provitamin D3 (3)-7-Dehydrochlesterol (3-beta)-cholesta-7-dien-3-ol (3beta)-Cholesta-5,7-dien-3-ol (3beta)-cholesta-7-dien-3-ol (3β)-7-去氢胆甾醇 3-Hydroxycholesta-5,7-diene 3BETA-HYDROXY-5,7-CHOLESTADIENE 3BETA-胆甾-5,7-二烯-3-醇 3β-Hydroxy-5,7-cholestadiene 3β-羟基胆甾-5,7-二烯 3β-胆甾-5,7-二烯-3-醇 5,7-CHOLESTADIEN-3-BETA-OL MONOHYDRATE 5,7-CHOLESTADIEN-3BETA-OL 5,7-Cholestadien-3-beta-ol 5,7-Cholestadien-3β-ol 5,7-Cholestandien-3.beta.-ol 5,7-Cholestandien-3beta-ol 5,7-胆甾二烯-3Β-醇 7,8-Didehydrocholesterol 7,8-didehydrocholesterol 7-DEHYDROCHOL
MDL NumberMFCD00003624
EC Number207-100-5
Merck Number14,2867
Beilstein Registry Number2224615
PubChem Substance ID439423
Chemical Name Translation(3S,9S,10R,13R,14R,17R)-10,13-二甲基-17-((R)-6-甲基庚-2-基)-2,3,4,9,10,11,12,13,14,15,16,17-十二氢-1H-环戊二烯[a]菲-3-醇
Wiswesser Line NotationL E5 B666 JU LUTJ A1 E1 FY1&3Y1&1 OQ
LabNetwork Molecule IDLN01278926
InChIInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
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分类

  • {SNA} Cell Biology, Cell Signaling and Neuroscience, Cholesterol and Cholesterol Metabolism, Lipids in Cell Signaling, Metabolic Pathways,
  • {SNA} Vitamin D,
  • {SNA} Vitamin D, Vitamin D3, Vitamins, 生化试剂
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, D, DA - DH, Vitamin D, Vitamin D3,
  • {SNA} Vitamin D, Vitamin D3, Vitamins, 细胞生物学, 营养研究
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, D, DA - DH, Nutrition Research, Vitamin D, Vitamin D3,
  • Steroids
  • {SN

产品应用

  • A vitamin precursor.

相关文献及参考

  • [1]. Xu L, et al. Oxysterols from free radical chain oxidation of 7-dehydrocholesterol: product and mechanistic studies. J Am Chem Soc. 2010 Feb 24;132(7):2222-32.

安全信息

RTECSFZ5650000
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S22 Do not breathe dust 不要吸入粉尘；
Storage condition -20°C Light Sensitive
WGK Germany3
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 60 gm/kg/2W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   NATWAY Naturwissenschaften.  (Springer-Verlag, Heidelberger Platz 3, D-1000
   Berlin 33, Fed. Rep. Ger.)  V.1-    1913-  Volume(issue)/page/year:
   60,525,1973

Hazard statements
  • H413 Maycauselonglastingharmfuleffectstoaquaticlife 可能对水生生物造成长期持续有害影响。
Precautionary statements
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....

其他信息

  • 方法一:猪皮中分离提取，亦可用胆甾醇经酯化、溴化、消除、水解制得。
  • MOL 文件:434-16-2.mol
  • Alfa Aesar:7-Dehydrocholesterol monohydrate, 97%(434-16-2)
  • Acros Organics:7-去氢胆固醇(含1M甲醇晶体) 7-Dehydrocholesterol, contains ca. 1 mole of methanol of crystallization, 97.50%(434-16-2)
  • 7-去氢胆固醇价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 111950250 7-去氢胆固醇 7-Dehydrocholesterol 97.5%, contains ca. 1 mole of methanol of crystallization 25 GR 1478元 2010/06/21 111950050 7-去氢胆固醇 7-Dehydrocholesterol 97.5%, contains ca. 1 mole of methanol of crystallization 5 GR 566元
  • 用途一:维生素D3的中间体。
  • 上游原料:胆固醇
  • F:8-10-23
  • 下游产品:维生素 D3
  • Sigma Aldrich:434-16-2(sigmaaldrich)

系列性分类

  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Pathways - Metabolomics
  4. Steroid Metabolism - Metabolic Pathways
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Lipids in Cell Signaling - Cell Signaling and Neuroscience
  5. Cholesterol and Cholesterol Metabolism - Lipids in Cell Signaling
  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. Oxygen Compounds 氧化合物
  5. Alcohols - Oxygen Compounds
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. D - Alphabetic
  5. DA - DH - D
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. D - Alphabetic
  5. DA - DH - D
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Vitamins - Nutrition Research
  4. Vitamin D - Vitamins
  5. Vitamin D3 - Vitamin D
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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