(1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-yl octadecanoate

• ChemBase ID: 168255
• Molecular Formular: C36H58O3
• Molecular Mass: 538.84392
• Monoisotopic Mass: 538.43859572
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)OC(=O)CCCCCCCCCCCCCCCCC)C)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C36H58O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(38)39-34-24-23-33-32-21-19-28-27-29(37)20-22-30(28)31(32)25-26-36(33,34)2/h20,22,27,31-34,37H,3-19,21,23-26H2,1-2H3/t31-,32-,33+,34+,36+/m1/s1
• InChIKey: KIADYVOYCQRXRE-IMTRJTTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl octadecanoate
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl octadecanoate
• Synonyms: (17β)-Estra-1,3,5(10)-triene-3,17-diol 17-Octadecanoate; Estradiol 17-Stearate; Estradiol 17-O-Octadecanoate

Database IDs

• CAS Number: 82205-00-3
• PubChem SID: 162262387
• PubChem CID: 67100

CALCULATED PROPERTIES

• Acid pKa: 10.327061
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 11.555686
• LogD (pH = 7.4): 11.5551815
• Log P: 11.555693
• Molar Refractivity: 162.6981 cm^3
• Polarizability: 64.63809 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 94°C

DETAILS

Toronto Research Chemicals - E888500

Estradiol 17-O-octadecanoate is one of the estradiol fatty acid esters which are the most potent of the naturally occurring steroidal estrogens.

REFERENCES

• Jones, D., et al.: J. Steroid Biochem., 22, 243 (1985)
• Odum, J., et al.: Reg. Toxicol. Pharmacol., 25, 176 (1985)
• Kanji, S., et al.: Clin. Endocrinol. Metab., 84, 2481 (1985)