[(3Bs,5ar,7s,8r,10ar,10bs)-7-hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methyl hexadecanoate
Basic information
- CAS
81760-46-5- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]1(O)C[C@]23CC[C@@H]4c5ccoc5CC[C@@]4(C)[C@@H]2CC[C@@H]1C3- InChIKey
DGPMHJKMSANHDM-XCPWRNKKSA-N- Molecular formula
- C36H58O4
- Average molar mass
- 554.8 g/mol
- Monoisotopic mass
- 554.43351033
Overview
(7-Hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl)methyl hexadecanoate has been reported in Coffea canephora and Coffea arabica with data available.
Names & identifiers
- Preferred name
- [(3Bs,5ar,7s,8r,10ar,10bs)-7-hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methyl hexadecanoate
- IUPAC
- [(1R,4S,12S,13R,16R,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate
- English name
- CAFESTOL PALMITATE
- Molecular formula
- C36H58O4
- Molecular weight
- 554.84
Names & synonyms
(7-Hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl)methyl hexadecanoate[(1R,4S,12S,13R,16R,17S)-17-Hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-yl]methyl hexadecanoate[(3bs,5ar,7s,8r,10ar,10bs)-7-hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methyl hexadecanoateDTXSID401002186CAFESTOL PALMITATEPubChem ID: 133758Hexadecanoic acid, [(3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methyl ester
Database identifiers
- CAS
81760-46-5- PubChem CID
- 133758
- DTXSID
DTXSID401002186
Properties
Computed structural properties
- XLogP
- 11.2
- Topological polar surface area
- 59.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 17
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 813
Physicochemical properties
- Melting point
- 43 · 43~44℃
- Boiling point
- 629.8 · 629.8±55.0 °C(Predicted)
- Density
- 1.06 · 1.06±0.1 g/cm3(Predicted)
- pka
- 13.91 · 13.91±0.40(Predicted)
- LogP
- 0.311 · 0.311 (est)
- FDA UNII
- 8 W9M3T86Y · P8W9M3T86Y
Chemistry & industry
Applications
UsesCafestol palmitate is an active constituent of green coffee beans. Cafestol palmitate can enhance glutathione S-transferase activity in the mouse. Cafestol palmitate also exhibits weak COX-2 inhibitory activity[1][2].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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