(4R)-4-[(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 102391
• Molecular Formular: C24H34O5
• Molecular Mass: 402.52376
• Monoisotopic Mass: 402.24062419
• SMILES: O=C1C[C@H]2CC(=O)[C@H]3[C@H]4[C@](C(=O)C[C@@H]3[C@@]2(C)CC1)([C@H](CC4)[C@H](C)CCC(=O)O)C
• Canonical SMILES: OC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)C(=O)C[C@H]1[C@H]2C(=O)C[C@H]2[C@]1(C)CCC(=O)C2)C
• InChI: InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
• InChIKey: OHXPGWPVLFPUSM-KLRNGDHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-5,9,16-trioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: dehydrocholic
• Synonyms: 3,7,12-Trioxo-5β-cholanic acid; 5β-Cholanic acid-3,5,12-trione; DEHYDROCHOLIC ACID; 3,7,12-Trioxo-5beta-cholan-24-oic acid; 3,7,12-Triketocholanic acid; 5β-Cholanic acid-3,5,12-trione; 3,7,12-Trioxo-5β-cholanic acid; Dehydrocholic acid; 3,7,12-三氧-5β-胆烷酸; 去氢胆酸

Database IDs

• CAS Number: 81-23-2
• EC Number: 201-335-7
• MDL Number: MFCD00066410
• Beilstein Number: 3226734
• Merck Index: 142868
• PubChem SID: 162091199; 24858665
• PubChem CID: 6674
• CHEMBL: 514446
• Chemspider ID: 6422
• KEGG ID: D06438
• Wikipedia Title: Dehydrocholic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.3482914
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.4595513
• LogD (pH = 7.4): 0.71172273
• Log P: 3.6390371
• Molar Refractivity: 108.0137 cm^3
• Polarizability: 42.773422 Å^3
• Polar Surface Area: 88.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble10 mg/mL; ethanol: soluble10 mg/mL, clear (hot)
• Melting Point: 231-234°C; 235-238°C; 238-240 °C
• Optical Rotation: [α]20/D +26±1°, c = 1% in ethanol; +26 (c=1 in ethanol)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: FZ2300000
• German water hazard class: 2
• TSCA Listed: 是
• GHS Hazard statements: H303
• GHS Precautionary statements: P312
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (T); 97%; 99%
• Description: anionic
• Empirical Formula (Hill Notation): C24H34O5

DETAILS

MP Biomedicals - 02101475

Free Acid
Crystalline

Sigma Aldrich - D3750

Biochem/physiol Actions
Bile Acid

Sigma Aldrich - 30830

Other Notes
In the production of chenodeoxycholic acid by bioconversion1