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

• ChemBase ID: 155970
• Molecular Formular: C28H44O3
• Molecular Mass: 428.64716
• Monoisotopic Mass: 428.32904527
• SMILES: C[C@H](C=C[C@H](C)C(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](C=C[C@@H](C(O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/t18-,19+,23-,24-,25+,26+,28-/m1/s1
• InChIKey: ZGLHBRQAEXKACO-WROXZXEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: 1α,25-Dihydroxycalciferol; 1α,25-Dihydroxyvitamin D2

Database IDs

• CAS Number: 60133-18-8
• MDL Number: MFCD00869499
• Beilstein Number: 5635017
• PubChem SID: 24850813; 162250108
• PubChem CID: 71312250

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.353792
• LogD (pH = 7.4): 4.353792
• Log P: 4.353792
• Molar Refractivity: 132.1207 cm^3
• Polarizability: 51.0291 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 63-23/24/25
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H361
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• 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: -70°C

Product Information

• Purity: ≥97.0% (sum of vitamin and previtamin, HPLC)
• Empirical Formula (Hill Notation): C28H44O3

DETAILS

Sigma Aldrich - 17944

Biochem/physiol Actions
Ergocalciferol (vitamin D2) is activated in vivo by hydroxylation to 25-hydroxyergocalciferol and 1α,25-dihydroxycalciferol. Activated Vitamin D2 molecules may be used in a wide range of studies to assess their effects on functions such as immune function and calcium homeostasis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17944.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.