(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

• ChemBase ID: 133032
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: C[C@H](CCCC(C)(C)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]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CCCC(O)(C)C)C)C)/C1
• InChI: InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
• InChIKey: JWUBBDSIWDLEOM-DTOXIADCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: 25-hydroxyvitamin D3
• Synonyms: (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol; 25-Hydroxycholecalciferol; 25-Hydroxyvitamin D; Calcidiol; Didrogyl; Hidroferol; Ro 8-8892; q; Calcifediol; 25-Hydroxyvitamin D3; 25-Hydroxycholecalciferol

Database IDs

• CAS Number: 19356-17-3
• EC Number: 242-990-9
• MDL Number: MFCD00867077
• PubChem SID: 24895612; 162227309
• PubChem CID: 5283731

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.654346
• LogD (pH = 7.4): 5.654346
• Log P: 5.654346
• Molar Refractivity: 125.0606 cm^3
• Polarizability: 48.829468 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 74-76°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 24/25-26-48/25
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H372
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - H4014

Biochem/physiol Actions
Ergocalciferol (vitamin D2) and 25-Hydroxycholecalciferol (vitamin D3) are the two form of vitamin D which are activated in vivo by hydroxylation. Vitamin D2 and D3 may be used in a wide range of studies to assess their effects on function such as immune function and calcium homeostasis.

Toronto Research Chemicals - C125700

A metabolite of Vitamin D. The principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator.

REFERENCES

• Morii, et al.: Arch. Biochem. Biophys., 120, 513 (1967)
• Blunt, et al.: Biochemistry, 7, 3317 (1967)
• Liu, et al.: Science, 311, 1770 (1967)