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

• ChemBase ID: 144275
• 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/t20-,23+,24-,25+,27-/m1/s1
• InChIKey: JWUBBDSIWDLEOM-DLBXBJKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3-{2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: (1S)-3-{2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• Synonyms: 25-Hydroxycholecalciferol solution; 25-Hydroxyvitamin D3 solution; 25-Hydroxycholecalciferol; 25-Hydroxyvitamin D3 monohydrate

Database IDs

• CAS Number: 63283-36-3
• EC Number: 200-578-6
• MDL Number: MFCD00867077
• Beilstein Number: 4270041
• PubChem SID: 162238490; 24850810
• PubChem CID: 6506392

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

• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 11; 24/25-26-48/25
• Safety Statements: 28-36/37-45; 7-16
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H300-H310-H330-H372
• GHS Precautionary statements: P210; 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: ≥99.0% (HPLC); 98% (CP)
• Concentration: 100 μg/mL in ethanol; 5 μg/mL in ethanol; 50 μg/mL in ethanol
• Shelf Life: 3 mo. at -20 °C (Please inquire with A href="mailto:isosales@sial.com">isosales@sial.com for a batch specific expiration date); 3 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date)
• Empirical Formula (Hill Notation): C27H44O2; C27H44O2 · H2O

DETAILS

Sigma Aldrich - 17938

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. 25-dihydroxycholecalciferol is a the major circulating form of vitamin D3 and a physiological precursor of 1α,25-Dihydroxycholecalciferol. The conversion is catalyzed by 25-Hydroxyvitamin D3 1-α-hydroxylase (VD3 1A hydroxylase) also known ascytochrome p450 27B1 (CYP27B1).