(1S,2R,5S,10S,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-14-carboxylic acid

• ChemBase ID: 156815
• Molecular Formular: C22H32O4
• Molecular Mass: 360.48708
• Monoisotopic Mass: 360.2300595
• SMILES: CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@@H]4C(=O)O)C)C
• Canonical SMILES: CC(=O)O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)O)C)C1)C
• InChI: InChI=1S/C22H32O4/c1-13(23)26-15-8-10-21(2)14(12-15)4-5-16-17-6-7-19(20(24)25)22(17,3)11-9-18(16)21/h4,15-19H,5-12H2,1-3H3,(H,24,25)/t15-,16-,17-,18-,19+,21-,22-/m0/s1
• InChIKey: WVHKCBDRQIXZLC-SPHVDITISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-14-carboxylic acid
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-14-carboxylic acid
• Synonyms: 3β-Acetoxy-5-etiocholenic acid; (-)-3β-Acetoxy-5-etienic acid; (-)-3β-乙酰氧基-5-本胆烯酸

Database IDs

• CAS Number: 51424-66-9
• EC Number: 257-197-3
• MDL Number: MFCD00042682
• Beilstein Number: 2707059
• PubChem SID: 162250952; 24845078
• PubChem CID: 251594

CALCULATED PROPERTIES

• Acid pKa: 4.772827
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8917637
• LogD (pH = 7.4): 1.1159031
• Log P: 3.6928585
• Molar Refractivity: 99.3571 cm^3
• Polarizability: 39.373833 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 237-241 °C
• Optical Rotation: [α]20/D -18.5±1°, c = 1% in acetone

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C22H32O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 00805

Other Notes
Steroidal acid used for the resolution of alcohols1