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81760-48-7 molecular structure
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{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 and InChIs

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

Cite this record

CBID:133178 http://www.chembase.cn/molecule-133178.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
{17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-yl}methyl acetate
IUPAC Traditional name
{17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-yl}methyl acetate
Synonyms
Cafestol acetate
CAS Number
81760-48-7
MDL Number
MFCD00133152
PubChem SID
24892399
162227455
PubChem CID
2517

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
C1305 external link Add to cart Please log in.
Data Source Data ID
PubChem 2517 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.75223  H Acceptors
H Donor LogD (pH = 5.5) 3.118153 
LogD (pH = 7.4) 3.118153  Log P 3.118153 
Molar Refractivity 97.7016 cm3 Polarizability 38.665073 Å3
Polar Surface Area 59.67 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - C1305 external link
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.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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