8-Dehydrocholesterol

Base Information

• Chemical Name: 8-Dehydrocholesterol
• CAS No.: 70741-38-7
• Molecular Formula: C27H44 O
• Molecular Weight: 384.646
• UNII: R85BA49SYS
• DSSTox Substance ID: DTXSID801315054
• Nikkaji Number: J52.996F
• Wikidata: Q27162187
• Metabolomics Workbench ID: 34529
• Mol file: 70741-38-7.mol

Synonyms:8-dehydrocholesterol;cholesta-5,8-dien-3 beta-ol

Chemical Property of 8-Dehydrocholesterol

Chemical Property:

• Vapor Pressure: 9.51E-12mmHg at 25°C
• Melting Point: 147-148 °C(Solv: chloroform (67-66-3); acetone (67-64-1))
• Boiling Point: 492.1°C at 760 mmHg
• PKA: 15.00±0.70(Predicted)
• Flash Point: 211.8°C
• PSA: 20.23000
• Density: 1g/cm³
• LogP: 7.45290
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 655

Purity/Quality:

99%min ^*data from raw suppliers

8-Dehydrocholesterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3=C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CCC3=C2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Description: 8-dehydro Cholesterol (8-DHC) is an isomer of the cholesterol precursor 7-DHC . It accumulates in tissues and plasma in patients with Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in DHCR7, the gene encoding 3β-hydroxysterol-Δ7-reductase, and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. 8-DHC levels are increased in serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 .
• Uses: 8-Dehydrocholesterol is an intermediate in the synthesis of Zymostenol, which is the derivative of Zymosterol (Z701520), an sterol intermediate in the biosynthesis of cholesterol (C432501).

Technology Process of 8-Dehydrocholesterol

There total 6 articles about 8-Dehydrocholesterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

7α-cholesta-5,8-dien-3β-yl acetate (3914-89-4) → cholesta-5,8(9)-dien-3β-ol (70741-38-7)

Guidance literature:

With lithium; In various solvent(s); at -20 ℃; Yield given; 30 min longer than required for the initial apperance of a blue color;

DOI:10.1021/jo00330a006

Reference yield:

7α-bromocholest-5-en-3β-ol benzoate (26048-46-4) → cholesta-5,8(9)-dien-3β-ol (70741-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium thiocyanate; acetone

2: benzene; methanol. KOH

With ammonium thiocyanate; potassium hydroxide; acetone; benzene;

Reference yield:

3β-benzoyloxy-cholesta-5,8-diene (53435-19-1) → cholesta-5,8(9)-dien-3β-ol (70741-38-7)

Guidance literature:

With potassium hydroxide; benzene;

DOI:10.1021/ja01640a023

upstream raw materials:

3β-benzoyloxy-cholesta-5,8-diene

7α-cholesta-5,8-dien-3β-yl acetate

7-Dehydrocholesteryl acetate

7α-bromocholest-5-en-3β-ol benzoate

Downstream raw materials:

5α-cholest-8-en-3β-ol

Refernces

• 1、 Anastasia,Fiecchi,Galli. "Synthesis of cholesta-5,8-dien-3β-ol". . p. 3421 - 3422. Retrieved 2007/10/02.