[(1R,4S,12S,13R,16R,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate

• ChemBase ID: 105683
• Molecular Formular: C36H58O4
• Molecular Mass: 554.84332
• Monoisotopic Mass: 554.43351034
• SMILES: O=C(OC[C@]1(O)C[C@@]23[C@H]([C@]4([C@@H](c5ccoc5CC4)CC2)C)CC[C@H]1C3)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@]1(O)C[C@]23C[C@@H]1CC[C@H]3[C@]1([C@H](CC2)c2ccoc2CC1)C
• InChI: InChI=1S/C36H58O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(37)40-27-36(38)26-35-23-19-30-29-21-24-39-31(29)20-22-34(30,2)32(35)18-17-28(36)25-35/h21,24,28,30,32,38H,3-20,22-23,25-27H2,1-2H3/t28-,30-,32+,34-,35-,36-/m1/s1
• InChIKey: DGPMHJKMSANHDM-XCPWRNKKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,4S,12S,13R,16R,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate
• IUPAC Traditional name: [(1R,4S,12S,13R,16R,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate
• Synonyms: CAFESTOL PALMITATE

Database IDs

• CAS Number: 81760-46-5
• PubChem SID: 162093874
• PubChem CID: 133758

CALCULATED PROPERTIES

• Acid pKa: 13.752215
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 9.598082
• LogD (pH = 7.4): 9.598082
• Log P: 9.598082
• Molar Refractivity: 162.1415 cm^3
• Polarizability: 64.44127 Å^3
• Polar Surface Area: 59.67 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C

DETAILS

MP Biomedicals - 02193747

A naturally occurring ester present in green coffee beans.

REFERENCES

• Lam, L.K.T., et al., Cancer Res. , 42 : 1193-98, (1982).