(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

• ChemBase ID: 72942
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: C1[C@@H](CC2=CC=C3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](/C=C/[C@@H](C(C)C)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC=C3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C1)C
• InChI: InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
• InChIKey: DNVPQKQSNYMLRS-APGDWVJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol; (1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: ergosterol
• Synonyms: (3β,22E)-Ergosta-5,7,22-trien-3β-ol; (24R)-Ergosta-5,7,22-trien-3β-ol; 24-Methylcholesta-5,7,22-trien-3β-ol; 24R-Methylcholesta-5,7,22E-trien-3β-ol; 24α-Methyl-22E-dehydrocholesterol; 3β-Hydroxyergosta-5,7,22-triene; Ergosterin; Provitamin D; Provitamin D2; Ergosterol; Ergosterol; Ergosta-5,7,22-trien-3-ol; (3β)-麦角-5,7,22-三烯甘油-3-醇; 3β-羟基-5,7,22-麦角三烯; 维生素原 D2; 麦角固醇

Database IDs

• CAS Number: 57-87-4
• EC Number: 200-352-7
• MDL Number: MFCD00003623
• Beilstein Number: 2338604
• PubChem SID: 24894628; 162037862
• PubChem CID: 444679

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.6324067
• LogD (pH = 7.4): 6.632407
• Log P: 6.632407
• Molar Refractivity: 127.1317 cm^3
• Polarizability: 49.356697 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Powder; White Solid
• Melting Point: 156-158 °C(lit.); 160-162°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• GHS Hazard statements: H413
• 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: 2-8°C

Product Information

• Purity: ≥75%; 95+%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2297

Research Area: Cancer
Biological Activity:
Ergosterol is a sterol and a biological precursor (a provitamin) to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. [1] Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Because ergosterol is present in fungal cell membranes yet absent in animal cell membranes, it is a useful target for antifungal drugs. It is also present in the cell membranes of some protists, such as trypanosomes. This is the basis for the use of some antifungals against West African sleeping sickness. [2][3]

Sigma Aldrich - E6510

包装
5, 10, 25 g in poly bottle

Toronto Research Chemicals - E599240

Most important of the provitamins D. Usually obtained from yeast which synthesizes it from simple sugars such as glucose. Vitamin (antirachitic).

REFERENCES

• Rajakumar K et al. Am J Public Health. 2007 Oct;97(10):1746-54.
• Bills, H., et al.: J. Biol. Chem., 80, 15 (1928)
• Castanheiro, R., et al.: Biorg. Med. Chem., 15, 6080 (1928)
• Pinto, M., et al.: Pharm. Pharmacol. Lett., 7, 125 (1928)