20-Oxopregn-5-en-3-yl acetate
Basic information
- CAS
1778-02-5- Standard SMILES
CC(=O)OC1CCC2(C)C(=CCC3C2CCC2(C)C(C(C)=O)CCC32)C1- InChIKey
CRRKVZVYZQXICQ-UHFFFAOYSA-N- Molecular formula
- C23H34O3
- Average molar mass
- 358.5 g/mol
- Monoisotopic mass
- 358.25079494
Names & identifiers
- Preferred name
- 20-Oxopregn-5-en-3-yl acetate
- IUPAC
- (17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate
- English name
- Pregnenolone acetate
- Molecular formula
- C23H34O3
- Molecular weight
- 358.51
Names & synonyms
20-Oxopregn-5-en-3-yl acetate(17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate1093959-59-114-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetateAntofinArtivisEnescorbPrevisoneSharmonePregenolone acetatePregnenolone-3-acetatePregn-5-en-20-one, 3.beta.-hydroxy-, acetate
Show more names
NSC 64827ACETOXYPREGNENOLONEPREGNENOLONE ACETATEprognenolone acetate5-Pregnenolone acetate
Pregn-5-en-20-one, 3-(acetyloxy)-, (3.beta.)-NCGC00160652-02NCIOpen2_008303SCHEMBL670748Pregn-5-en-20-one, acetateNSC64827CCG-56424STK061707
Database identifiers
- CAS
1778-02-5- PubChem CID
- 15686
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 650
Experimental & physicochemical properties
CosmeticsSkin conditioning
Physicochemical properties
- Melting point
- 149 · 149-152 °C(lit.)
- alpha
- 22 · 22 º (c=2, C2H5OH 23 ºC)
- Boiling point
- 430.93 °C · 430.93°C (rough estimate)
- Density
- 1.0816 · 1.0816 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White
- optical activity
- 20 · [α]20/D +19°, c = 1 in ethanol
- Merck
- 14 · 14,7733
- BRN
- 2062850 · 2062850
- Cosmetics Ingredients Functions
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
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29153900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use ClassificationCosmetics -> Skin conditioning
Applications
UsesPregnenolone acetate is an intermediate in the synthesis of progesterone. It is uses as a glucocorticoid and as a skin-conditioning and skin anti-aging agent. It acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. It has also been shown to stimulate locomotor activity and neuronal function in rats.
Preparation methods
PreparationPregnenolone acetate can be prepared by catalytic hydrogenation (16-position double bond) of 16-Dehydropregnenolone acetate.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionPregnenolone acetate is a steroid ester. It is a pregnenolone derivative, a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…