beta-Cortolone
Basic information
- CAS
667-66-3- Standard SMILES
C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)[C@H](O)CO- InChIKey
JXCOSKURGJMQSG-AIEJOZITSA-N- Molecular formula
- C21H34O5
- Average molar mass
- 366.5 g/mol
- Monoisotopic mass
- 366.24062418
Overview
Beta-Cortolone is a 21-hydroxy steroid.
Names & identifiers
- Preferred name
- beta-Cortolone
- IUPAC
- (3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-3,17-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one
- English name
- (3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-3,17-dihydr oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopen ta[a]phenanthren-11-one
- Molecular formula
- C21H34O5
- Molecular weight
- 366.495
Names & synonyms
Beta-Cortolone667-66-3RefChem:1192395beta-11-oxo-pregnane-3alpha, 11beta,17, 20R, 21-tetrolb-Cortolone(3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-3,17-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-oneI(2)-Cortoloneorb2814625SCHEMBL30332229CHEBI:175712DTXSID201318212NSC56997
Show more names
β-Cortolone2-Cortoloneβ-Cortolone D55β-pregnan-3α, 17, 20β, 21-tetrol-11-one3α,17α,20β,21-Tetrahydroxy-5β-Pregnan-11-One(20R)-3α,17α,20,21-Tetrahydroxy-5β-pregnan-11-onePregnan-11-one, 3,17,20,21-tetrahydroxy-, (3α,5β,20R)-(3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-3,17-dihydr oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopen ta[a]phenanthren-11-one
LMST02030230NSC-56997HY-W779504T2030993alpha,17,20,21-Tetrahydroxy-5beta-pregnan-11-one5beta-11-oxo-pregnane-3alpha,11beta,17,20R,21-tetrol5beta-11-oxo-pregnane-3alpha, 11beta ,17, 20R, 21-tetrol
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 593
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Physicochemical properties
- Melting point
- 249 · 249-258oC
- Boiling point
- 564.1 · 564.1±50.0 °C(Predicted)
- Density
- 1.248 · 1.248±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly, Heated), Pyridine (Slightly)
- pka
- 13.95 · 13.95±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P305+P351+P338-P332+P313-P362+P364-P337+P313
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P321-P305+P351+P338-P332+P313-P362+P364-P337+P313
Chemistry & industry
Applications
Usesβ-Cortolone is a metabolite of Cortisol (H714615), a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.
Additional notes
DefinitionChEBI: Beta-Cortolone is a 21-hydroxy steroid.
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Compound notes
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