5alpha-Cholestan-3-one

HCID 92128

Substructure search Find similar structures

Basic information

CAS: 566-88-1
Standard SMILES: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: PESKGJQREUXSRR-UXIWKSIVSA-N
Molecular formula: C27H46O
Average molar mass: 386.7 g/mol
Monoisotopic mass: 386.35486609

Overview

5alpha-cholestan-3-one is a 3-oxo-5alpha- steroid that is 5alpha-cholestane substituted by an oxo group at position 3. It has a role as a mammalian metabolite. It is a 3-oxo-5alpha-steroid and a 3-oxocholestane. It derives from a hydride of a 5alpha-cholestane.

Names & identifiers

Preferred name: 5alpha-Cholestan-3-one
IUPAC: (5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
English name: 5alpha-Cholestan-3-one
Molecular formula: C27H46O
Molecular weight: 386.65

Names & synonyms

5alpha-Cholestan-3-one566-88-15alpha-Cholestanone(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-oneCHEBI:17762DTXSID001016294(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-oneRefChem:1073377DTXCID2015060515A-Cholestan-3-one5|A-Cholestan-3-one5alpha-Cholestane-3-one

Show more names

CHOLESTANONE5α-Cholestan-3-one5αZK-460235α-Cholestanone-Cholestan-3-one5à-cholestan-3-oneCHOLESTAN-3-ONE(RG)

(5alpha)-Cholestan-3-one(5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-17-((R)-6-methylheptan-2-yl)tetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-oneCholestan-3-one5-a-Cholestan-3-one3-Keto-5alpha-cholestane5-alpha-Cholestan-3-oneMFCD00065901Cholestan-3-one, (5a)-

Database identifiers

CAS: 566-88-1
PubChem CID: 92128
DTXSID: DTXSID001016294
ChEMBL: CHEMBL69941
ChEBI: CHEBI:17762
Nikkaji: J149.976I

Properties

Computed structural properties

XLogP: 8.9
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 5
Heavy atoms: 28
Formal charge: 0
Complexity: 579

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]

SpringerMaterials PropertiesCrystal structure

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point128 - 130 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 128 · 128-133 °C
alpha: 20 · [α]D20 +40～+44° (c=1, CHCl3)
Boiling point: 452.9 · 452.9±13.0 °C(Predicted)
Density: 0.953 · 0.953
storage temp.: Refrigerator
solubility: Chloroform (Sparingly)
form: crystalline
color: White to Off-White
Water Solubility: Insoluble in water.
BRN: 2625580 · 2625580
InChIKey: PESKGJQREUXSRR-UXIWKSIVSA-N
SMILES: [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
safety_code: 24/25
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Applications

UsesIt is employed as a intermediate for organic synthesis.

Uses5alpha-Cholestan-3-one

Upstream & downstream products

Upstream raw materials

Methyl 5α-cholestan-3β-yl ether NSC23921 Cholest-1-en-3-one, (5α)-Spiro[1,3-dioxolane-2,3'-[5α]cholestane]5-CHOLESTEN-3-ONE 5beta-Cholestan-3-one 4-Cholesten-3-one

Downstream products

Dihydrocholesterol (5α)-25-Hydroxycholestan-3-one

Suppliers43 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]

普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 5alpha-cholestan-3-one is a 3-oxo-5alpha- steroid that is 5alpha-cholestane substituted by an oxo group at position 3. It has a role as a mammalian metabolite. It is a 3-oxo-5alpha-steroid and a 3-oxocholestane. It derives from a hydride of a 5alpha-cholestane.