Cholest-4-en-3-on

Cholest-4-en-3-one

HCID 91477

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Grundinformationen

CAS: 601-57-0
Standard-SMILES: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: NYOXRYYXRWJDKP-GYKMGIIDSA-N
Summenformel: C27H44O
Durchschnittliche Molmasse: 384,6 g/mol
Monoisotopische Masse: 384,33921603

Überblick

Cholest-4-en-3-one is a cholestanoid that is cholest-4-ene substituted by an oxo group at position 3. It has a role as a plant metabolite and a human metabolite. It is a 3-oxo-Delta(4) steroid and a cholestanoid.

Namen und Bezeichner

Bevorzugter Name: Cholest-4-en-3-one
IUPAC: (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Lokaler Name: Cholest-4-en-3-on
Englischer Name: 4-Cholesten-3-one
Summenformel: C27H44O
Molmasse: 384.64

Namen und Synonyme

4-Cholesten-3-oneCholestenone601-57-0cholest-4-en-3-one3-Oxocholest-4-ene7T94NHD99CDTXSID90872379CHEBI:16175NSC-63000NSC-134926(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one

Weitere Namen anzeigen

4-Cholestenone4-Cholestene-3-oneCHOLEST-4-ENE-3-ONE

RefChem:576025DTXCID40820027210-005-1Cholesterone(+)-4-Cholesten-3-one3-Oxo-4-cholestene3-Keto-4-cholestenedelta(sup 4)-Cholestenone

Datenbank-Bezeichner

CAS: 601-57-0
PubChem CID: 91477
DTXSID: DTXSID90872379
ChEMBL: CHEMBL63243
ChEBI: CHEBI:16175
UNII: 7T94NHD99C
EC Number: 210-005-1
Nikkaji: J73F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 8,4
Polarare Oberfläche (TPSA): 17,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 5
Schwere Atome: 28
Formalladung: 0
Komplexität: 630

Experimentelle und physikochemische Eigenschaften

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

SpringerMaterials PropertiesCrystal structure

Melting Point79 - 82 °C

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 79 · 79-82 °C
Siedepunkt: 451.27 °C · 451.27°C (rough estimate)
Dichte: 0.9717 · 0.9717 (rough estimate)
Brechungsindex: 1.51 · 1.5100 (estimate)
storage temp.: -20 °C · -20°C
Löslichkeit: Chloroform (Sparingly), Methanol (Slightly, Heated)
Aggregatzustand: Solid
Farbe: White to Off-White
Wasserlöslichkeit: 0.5 g/L · <0.5 g/L
BRN: 4707774 · 4707774
Stabilität: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey: NYOXRYYXRWJDKP-GYKMGIIDSA-N
SMILES: [H][C@@]12[C@]([C@](CC3)(C)C(CC2)=CC3=O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)C
CAS Datenbank: 601 · 601-57-0(CAS DataBase Reference)
NIST chemische Informationen: -4 · Cholest-4-en-3-one(601-57-0)
EPA chemische Informationen: -4 · Cholest-4-en-3-one (601-57-0)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

H413 (95%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAquatic Chronic 4 (95%)

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
hs_code: 29142900
RTECS-Nr.: FZ7700000
risk_code: 36/37/38
hazard_code: Xi
safety_code: 22-24/25-36-26
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsGall Bladder

Cellular LocationsExtracellular

Verwendung und Herstellung

General Manufacturing InformationCholest-4-en-3-one: ACTIVE

Anwendungen · 2 Einträge

BeschreibungCholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.

Verwenden4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.