(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 126222
• Molecular Formular: C28H46O
• Molecular Mass: 398.66424
• Monoisotopic Mass: 398.35486609
• SMILES: O[C@@H]1CC2=CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@@H]34)[C@@H](C=C[C@H](C)C(C)C)C)C)[C@@]2(C)CC1
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[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/C28H46O/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/h7-9,18-20,22-26,29H,10-17H2,1-6H3/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
• InChIKey: OILXMJHPFNGGTO-ZRUUVFCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,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]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: brassicasterol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: 24(R)-Methylcholesta-5,22E-dien-3β-ol; 24-Methylcholesta-5,22-dien-3β-ol; Brassicasterin; Ergosta-5,22(E)-dien-3β-ol; Δ5,22-Ergostadien-3β-ol; Δ5,22-Ergostadienol; brassicasterol; (3β,22E)-ergosta-5,22-dien-3-ol; 24β-methylcholesta-5,22-dien-3 beta-ol; ergosta-5,22-dien-3β-ol; Brassicasterol

Database IDs

• CAS Number: 474-67-9
• PubChem SID: 162220562
• PubChem CID: 6432458; 441827
• Chemspider ID: 4444704
• Unique Ingredient Identifier: 2B0KG2XFOF
• Wikipedia Title: Brassicasterol

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.0379863
• LogD (pH = 7.4): 7.0379863
• Log P: 7.0379863
• Molar Refractivity: 126.2817 cm^3
• Polarizability: 49.590298 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White solid
• Melting Point: 150–151 °C
• Flash Point: Non-flammable

DETAILS

Toronto Research Chemicals - B676850

A phytosterol found in canola oil, rapeseed oil, marine algae and shellfish. This compound has been shown to inhibit sterol Δ24-reductase, an enzyme involved in the mammalian cholesterol biosynthesis pathway.

REFERENCES

• Bishop, G.J., et al.: Plant Cell Physiol. 42, 114, (2001)
• Fernandez, C., et al., Biochem. J. 366, 109 (2001)