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

• ChemBase ID: 144282
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: C[C@H](C=C[C@H](C)C(C)C)[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(C)C)C)C)C)/C1
• InChI: InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/t20-,22+,25-,26+,27-,28+/m0/s1
• InChIKey: MECHNRXZTMCUDQ-FWTXJDITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3E)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol; (1S)-3-{2-[(1R,3aS,7aR)-1-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: β-ol; (1S)-3-{2-[(1R,3aS,7aR)-1-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• Synonyms: (3β,5E,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol; 5,6-trans-Ergocalciferol; 5,6-trans-Vitamin D2; Calciferol solution; Vitamin D2 solution; Calciferol; Ercalciol; Ergosterol irradiated; Irradiated ergosterol; Vitamin D2; Ergocalciferol; Ergocalciferol; Ergocalciferol (D2); 照射麦角甾醇; 维生素 D2; 钙化醇; 骨化醇; 麦角钙化醇; 麦角钙化甾醇; 麦角钙化甾醇; 麦角钙化甾醇 (D2)

Database IDs

• CAS Number: 50-14-6; 51744-66-2
• EC Number: 200-014-9; 200-578-6
• MDL Number: MFCD00166988
• Beilstein Number: 1916682
• PubChem SID: 24890108; 162238497; 24871402
• PubChem CID: 71311077

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.050558
• LogD (pH = 7.4): 7.050558
• Log P: 7.050558
• Molar Refractivity: 128.8897 cm^3
• Polarizability: 49.86576 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white to yellowish
• Melting Point: 114-118 °C; 114-118 °C(lit.)
• Flash Point: 14 °C; 57.2 °F
• Optical Rotation: [α]20/D +105±2°, c = 4% in ethanol

Safety Information

• RTECS: KE1050000
• European Hazard Symbols: Flammable (F); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 1; 2
• 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; H301-H311-H330-H372
• GHS Precautionary statements: P210; P260-P280-P284-P301 + P310-P310
• 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; 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 98% (CP)
• Concentration: 100 μg/mL in ethanol
• Grade: analytical standard
• Packaging: ampule of 100 mg
• Shelf Life: 6 mo. at -20 °C (Please inquire with isosales@sial.com for a batch specific expiration date.)
• Mol. Weight: mol wt 396.65 by atom % calculation
• Feature: standard type fat soluble vitamin
• Empirical Formula (Hill Notation): C28H44O

DETAILS

Sigma Aldrich - 95220

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 - V676060

5,6-trans-Vitamin D2 is an isomer as well as one of the main decomposition products of Vitamin D2 (V676040).

REFERENCES

• Yamaoka, K. et al.: Yakuzaigaku, 45, 53 (1985)
• Kobayashi, T. et al.: J. Nutrit. Sci. Vitaminol., 23, 281 (1985)