(4R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol

• ChemBase ID: 153884
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C[C@H](C[C@H](CC(C)(C)O)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](CCC1=C)O)C
• Canonical SMILES: O[C@@H](CC(O)(C)C)C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C\1/C[C@@H](O)CCC1=C)C
• InChI: InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/t19-,22+,23-,24-,25+,27-/m1/s1
• InChIKey: JVBPQHSRTHJMLM-YEMUBGRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol
• IUPAC Traditional name: (4R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol
• Synonyms: (23R)-23,25-Dihydroxycholecalciferol; (23R)-23,25-Dihydroxyvitamin D3

Database IDs

• CAS Number: 81738-09-2
• MDL Number: MFCD12912385
• PubChem SID: 162248023
• PubChem CID: 71311748

CALCULATED PROPERTIES

• Acid pKa: 14.929132
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.1948333
• LogD (pH = 7.4): 4.1948338
• Log P: 4.1948338
• Molar Refractivity: 126.6865 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C27H44O3

DETAILS

Sigma Aldrich - 55171

Application
able to increase the plasma lactone concentration1
Biochem/physiol Actions
Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 23,25-Dihydroxyvitamin D3 is synthesized by the human placenta and by kidney cortex mitochondria.