8-Dehydrocholesterol
Basic information
- CAS
70741-38-7- Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3- InChIKey
VUKORTMHZDZZFR-BXAZICILSA-N- Molecular formula
- C27H44O
- Average molar mass
- 384.6 g/mol
- Monoisotopic mass
- 384.33921602
Overview
8-Dehydrocholesterol is a steroid.
Names & identifiers
- Preferred name
- 8-Dehydrocholesterol
- IUPAC
- (3S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- (3S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- Molecular formula
- C27H44O
- Molecular weight
- 384.64
Names & synonyms
8-DehydrocholesterolCholesta-5,8-dien-3beta-olCholesta-5,8-dien-3 beta-ol8-DHCR85BA49SYS3b-Cholesta-5,8-dien-3-olRefChem:10704270741-38-78-Dehydro CholesterolCholesta-5,8-dien-3-ol,(3b)-Cholesta-5,8-dien-3-ol, (3beta)-8(9)-dehydrocholesterol
Show more names
8DHCΔ5,8 SterolΔ5,8-Cholest-dienolCholesta-5,8-dien-3β-olcholesta-5,8(9)-dien-3-olCholesta-5,8(9)-dien-3b-olcholesta-5,8(9)-dien-3β-ol
(3S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-olVUKORTMHZDZZFR-BXAZICILSA-NDTXSID801315054(3beta)-Cholesta-5,8-dien-3-olUNII-R85BA49SYScholesta-5,8-dien-3b-olSCHEMBL2106790CHEBI:89982
Database identifiers
Properties
Computed structural properties
- XLogP
- 7.4
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 655
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 147 · 147-148 °C(Solv: chloroform (67-66-3); acetone (67-64-1))
- Boiling point
- 492.1 · 492.1±44.0 °C(Predicted)
- Density
- 1 · 1.00±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 15 · 15.00±0.70(Predicted)
- color
- White to Pale Yellow
- InChIKey
- VUKORTMHZDZZFR-BXAZICILSA-N
- SMILES
- C[C@]1(CC2)C(CCC1C(CCCC(C)C)C)C3=C2[C@](CC[C@H](O)C4)(C)C4=CC3
- FDA UNII
- 85 BA49SYS · R85BA49SYS
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Metabolite PathwaysAlendronate Action Pathway
Applications
Description8-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 .
Uses8-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).
Additional notes
DefinitionChEBI: 8-Dehydrocholesterol is a steroid.
Related reactions
3 records
Compound notes
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