{17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-yl}methyl acetate

• ChemBase ID: 133178
• Molecular Formular: C22H30O4
• Molecular Mass: 358.4712
• Monoisotopic Mass: 358.21440944
• SMILES: CC(=O)OCC1(CC23CCC4c5ccoc5CCC4(C2CCC1C3)C)O
• Canonical SMILES: CC(=O)OCC1(O)CC23CC1CCC3C1(C(CC2)c2ccoc2CC1)C
• InChI: InChI=1S/C22H30O4/c1-14(23)26-13-22(24)12-21-9-5-17-16-7-10-25-18(16)6-8-20(17,2)19(21)4-3-15(22)11-21/h7,10,15,17,19,24H,3-6,8-9,11-13H2,1-2H3
• InChIKey: PTGGVIKFNQSFBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0^1,^1^3.0^4,^1^2.0^5,^9]nonadeca-5(9),6-dien-17-yl}methyl acetate
• IUPAC Traditional name: {17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.0^1,^1^3.0^4,^1^2.0^5,^9]nonadeca-5(9),6-dien-17-yl}methyl acetate
• Synonyms: Cafestol acetate

Database IDs

• CAS Number: 81760-48-7
• MDL Number: MFCD00133152
• PubChem SID: 24892399; 162227455
• PubChem CID: 2517

CALCULATED PROPERTIES

• Acid pKa: 13.75223
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.118153
• LogD (pH = 7.4): 3.118153
• Log P: 3.118153
• Molar Refractivity: 97.7016 cm^3
• Polarizability: 38.665073 Å^3
• Polar Surface Area: 59.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - C1305

Other Notes
Furan-containing diterpene from green coffee beans.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1305.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Biochem/physiol Actions
Cafestol is a coffee-specific diterpene that induces apoptosis in cells associated with colorectal and renal cancer (Caki cells). Cafestol is used to study mechanisms of anti-oxidation related to hydrogen peroxide induced oxidative stress and DNA damage.