(8S,9S,10R,13R,14S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Basic information
- CAS
1058-61-3- Standard SMILES
CC[C@H](CC[C@@H](C)C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C- InChIKey
RUVUHIUYGJBLGI-VCVIHXEESA-N- Molecular formula
- C29H48O
- Average molar mass
- 412.7 g/mol
- Monoisotopic mass
- 412.37051615
Overview
Sitostenone has been reported in Homalolepis floribunda with data available.
Names & identifiers
- Preferred name
- (8S,9S,10R,13R,14S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- IUPAC
- (8S,9S,10R,13R,14S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- English name
- β-Sitostenone
- Molecular formula
- C29H48O
- Molecular weight
- 412.69
Names & synonyms
BETA-ROSASTEROL4-Stigmasten-3-one(8S,9S,10R,13R,14S)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-oneSCHEMBL19506866NSC49082NSC-49082NS00125151F92958STIGMAST-4-EN-3-ONESitostenoneβ-SitostenoneStigmastenone
Show more names
Nsc 49082SitosteneB-SITOSTENONβ-SitostenoneBETA-SITOSTENONESITOSTENONE, BETA-
Database identifiers
- CAS
1058-61-3- PubChem CID
- 241573
Properties
Computed structural properties
- XLogP
- 9.3
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 674
Physicochemical properties
- Melting point
- 82 °C · 82 °C(Solv: methanol (67-56-1))
- Boiling point
- 503.8 · 503.8±17.0 °C(Predicted)
- Density
- 0.97 · 0.97±0.1 g/cm3(Predicted)
- solubility
- 0.33 mg/mlEthanol: · DMF: 0.33 mg/mlEthanol: Slightly soluble
- form
- Solid
- color
- White to off-white
- LogP
- 10.24 · 10.240 (est)
- FDA UNII
- 85907 B49EV · 85907B49EV
- EPA Substance Registry System
- -4 · Stigmast-4-en-3-one (1058-61-3)
Chemistry & industry
Applications
Usesβ-Sitostenone is a sterols that can be isolated from Cochlospermum vitifolium.β-Sitostenone inhibits tyrosinase activity, and has anti-melanogenic and anti-tumor activities[1][2][3].
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Beta-sitostenone is a steroid and a C29-steroid. It has a role as a metabolite. It derives from a hydride of a stigmastane.
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Compound notes
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