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

• ChemBase ID: 144411
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• 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](C[C@@H](C1=C)O)O)C
• Canonical SMILES: O[C@H]1C[C@H](O)C(=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/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/t18-,22-,23-,24+,25+,27-/m1/s1
• InChIKey: GMRQFYUYWCNGIN-ZVUFCXRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol; (1R,3S,5E)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: calcitriol oral solution; 1,25-dihydroxycholecalciferol
• Synonyms: 1α,25-Dihydroxycalciferol solution; 1α,25-Dihydroxyvitamin D2 solution; 1α,25-Dihydroxycholecalciferol; Calcitriol; 1α,25-Dihydroxyvitamin D3; (1R,3S,5E)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol; (1α,3β,5E,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol; 1,25-Dihydroxy-5,6-trans-vitamin D3; 1α,25-Dihydroxy-5,6-trans-vitamin D3; 5,6-trans-1α,25-Dihydroxyvitamin D3; 5,6-trans-Calcitriol

Database IDs

• CAS Number: 32222-06-3; 73837-24-8
• EC Number: 250-963-8; 200-578-6
• MDL Number: MFCD00867079
• Beilstein Number: 7559394
• PubChem SID: 162238626; 24850808
• PubChem CID: 5283740

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.350741
• LogD (pH = 7.4): 4.350741
• Log P: 4.350741
• Molar Refractivity: 126.5325 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 14 °C; 57.2 °F

Safety Information

• RTECS: FZ4645000
• European Hazard Symbols: Flammable (F); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 11; 63-26/27/28
• Safety Statements: 36/37/39-45; 7-16
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H300-H310-H330-H361
• 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 1
• Storage Temperature: -20°C; -70°C

Pharmacology Properties

• Gene Information: human ... VDR(7421)

Product Information

• Purity: ≥97.0% (HPLC); 95% (CP); 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 isosales@sial.com for a batch specific expiration date)
• Empirical Formula (Hill Notation): C27H44O3; C28H44O3

DETAILS

Sigma Aldrich - 17936

Biochem/physiol Actions
Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Toronto Research Chemicals - C144510

An impurity of Calcitriol (C144500). The trans isomer of Calcitriol.

REFERENCES

• Myrtle, J.F., et al.: J. Biol. Chem., 245, 1190 (1970)
• Lawson, D.E.M., et al.: Nature, 230, 228 (1970)
• Norman, A.W., et al.: Science, 173, 51 (1970)
• Suda, T., et al.: Vitamins, 45, 175 (1970)
• Muindi, J.R., et al.: Clin. Pharmacol. Ther., 72, 648 (2002