(1S)-3-{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-methylidenecyclohexan-1-ol

• ChemBase ID: 144262
• Molecular Formular: C28H44O2
• Molecular Mass: 412.64776
• Monoisotopic Mass: 412.33413065
• 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](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](C=C[C@@H](C(O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/t20-,21+,24+,25-,26+,28-/m1/s1
• InChIKey: KJKIIUAXZGLUND-ULHIVVETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3-{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-methylidenecyclohexan-1-ol
• IUPAC Traditional name: (1S)-3-{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-methylidenecyclohexan-1-ol
• Synonyms: 25-Hydroxyergocalciferol solution; 25-Hydroxycalciferol solution; 25-Hydroxyvitamin D2 solution; 25-Hydroxyergocalciferol; 25-Hydroxycalciferol; 25-Hydroxyvitamin D2

Database IDs

• CAS Number: 21343-40-8
• EC Number: 200-578-6
• MDL Number: MFCD02683431
• Beilstein Number: 4716773
• PubChem SID: 24850809; 162238478
• PubChem CID: 71311065

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.6573973
• LogD (pH = 7.4): 5.6573973
• Log P: 5.6573973
• Molar Refractivity: 130.6488 cm^3
• Polarizability: 50.44043 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• 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+)
• German water hazard class: 1; 3
• 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
• Storage Temperature: -20°C; -70°C

Product Information

• Purity: ≥98.0% (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 isosales@sial.com for a batch specific expiration date); 6 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date.)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C28H44O2

DETAILS

Sigma Aldrich - 17937

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. 17937.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.