(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-5-one

• ChemBase ID: 101927
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• SMILES: [C@@]12([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC[C@@H]1[C@@H](CCCC(C)C)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-5-one; (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: cholestenone
• Synonyms: 4-Cholesten-3-one; (+)-4-Cholesten-3-one; 4-Cholesten-3-one; Cholestenone; 3-Keto-4-cholestene; 3-Oxo-4-cholestene; DELTA4-CHOLESTEN-3-ONE; (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; 4-Cholesten-3-one; 4-胆甾烯-3-酮; 胆甾-4-烯-3-酮; 胆甾烯酮; (+)-4-胆甾烯-3-酮; 4-胆甾烯-3-酮

Database IDs

• CAS Number: 601-57-0
• EC Number: 210-005-1
• MDL Number: MFCD00003663
• Beilstein Number: 2224119; 4707774
• PubChem SID: 24851303; 24856205; 162088569
• PubChem CID: 91477

CALCULATED PROPERTIES

• Acid pKa: 19.087826
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.680135
• LogD (pH = 7.4): 7.680135
• Log P: 7.680135
• Molar Refractivity: 119.5651 cm^3
• Polarizability: 47.426888 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 79-81 °C(lit.); 79-81°C; 79-82 °C
• Optical Rotation: [α]/D +93±3°, c = 2 in chloroform; [α]23/D +91.0°, c = 2 in chloroform; +93 (c=1 in chloroform)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: FZ7700000
• German water hazard class: 3
• TSCA Listed: 是
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (UV); 95+%; 97%; 98%; 98+%
• Grade: purum
• Impurities: ~1% cholesterol
• Empirical Formula (Hill Notation): C27H44O

DETAILS

MP Biomedicals - 05215819

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 188174

Packaging
1, 10 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 188174.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.