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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28O3
Molecular Weight 316.4345
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAFESTOL

SMILES

[H][C@@]12C[C@]3(C[C@]1(O)CO)CC[C@]4([H])C5=C(CC[C@@]4(C)[C@]3([H])CC2)OC=C5

InChI

InChIKey=DNJVYWXIDISQRD-HWUKTEKMSA-N
InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H28O3
Molecular Weight 316.4345
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Cafestol is a diterpene molecule found in coffee beans and has anticarcinogenic properties. Cafestol, a bioactive substance in coffee, increases glucose-stimulated insulin secretion in vitro and increases glucose uptake in human skeletal muscle cells. Cafestol possesses antidiabetic properties in KKAy mice. Consequently, cafestol may contribute to the reduced risk of developing T2D in coffee consumers and has a potential role as an antidiabetic drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
The coffee-specific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism.
1998 Aug
The Cap'n'Collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes.
2001 Apr 15
Protective effects of coffee diterpenes against aflatoxin B1-induced genotoxicity: mechanisms in rat and human cells.
2001 Jun
Coffee and its chemopreventive components Kahweol and Cafestol increase the activity of O6-methylguanine-DNA methyltransferase in rat liver--comparison with phase II xenobiotic metabolism.
2003 Jan 28
Coffee diterpenes prevent the genotoxic effects of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and N-nitrosodimethylamine in a human derived liver cell line (HepG2).
2005 Mar
Reduction in antioxidant defenses may contribute to ochratoxin A toxicity and carcinogenicity.
2007 Mar
Hepatoprotective and antioxidant effects of the coffee diterpenes kahweol and cafestol on carbon tetrachloride-induced liver damage in mice.
2007 Nov
Induction of cancer chemopreventive enzymes by coffee is mediated by transcription factor Nrf2. Evidence that the coffee-specific diterpenes cafestol and kahweol confer protection against acrolein.
2008 Feb 1
Cafestol, a coffee-specific diterpene, induces apoptosis in renal carcinoma Caki cells through down-regulation of anti-apoptotic proteins and Akt phosphorylation.
2011 Apr 25
Optimization of the isolation and quantitation of kahweol and cafestol in green coffee oil.
2013 Dec 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Human study: In a randomized, double-blind crossover study, 10 healthy male volunteers received either pure cafestol (61-64 mg/d) or a mixture of cafestol (60 mg/d) and kahweol (48-54 mg/d) for 28 d. Relative to baseline values, cafestol raised mean (+/-SEM) total serum cholesterol concentrations by 0.79 +/- 0.14 mmol/L (31 +/- 5 mg/dL), low-density-lipoprotein (LDL) cholesterol by 0.57 +/- 0.13 mmol/L (22 +/- 5 mg/dL), fasting triacy-glycerols by 0.65 +/- 0.12 mmol/L (58 +/- 11 mg/dL), and alanine aminotransferase by 18 +/- 2 U/L. https://www.ncbi.nlm.nih.gov/pubmed/9022539
Hamsters: For the experiment, 60 hamsters were divided into three equal groups and placed on one of three diets. The animals in Group I received a normal diet, whereas the animals in Groups II and III received the same diet supplemented with a 50:50 mixture of kahweol and cafestol. The content of the kahweol and cafestol mixture in these two diets was 0.2 g/kg of food (Group II) and 2.0 g/kg of food (Group III). Multiple tumors were common in animals treated with DMBA; however, the animals receiving kahweol and cafestol in the diet (2 g/kg of food) exhibited a 35% reduction in tumor burden.
Route of Administration: Oral
To evaluate the potential cell morphological changes as a result of treatment with cafestol and kahweol in malignant mesothelioma cells, MSTO-211H cells were treated with cafestol (0–90 uM) or kahweol (0–60 uM) of various concentrations and monitored for 48 hrs. The MSTO-211H cells was changed to round cell shape, cell shrinkage was observed, and cell volume was decreased in those treated with cafestol (60 and 90 uM) and kahweol (40 and 60 uM). The IC50 value of the cafestol and kahweol after 48 hrs of incubation was estimated as 82.07 uM and 56.00 uM in MSTO-211H cells and H28 cells, respectively. Cell viabilities were calculated as 99.3 ± 1.8%, 75.1 ± 2.6%, and 42.1 ± 2.2% of the control at 30, 60, and 90 uM cafestol in MSTO-211H cells and H28 cells, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:39:37 UTC 2023
Edited
by admin
on Fri Dec 15 18:39:37 UTC 2023
Record UNII
AC465T6Q6W
Record Status Validated (UNII)
Record Version
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Name Type Language
CAFESTOL
MI  
Common Name English
5A,8-METHANO-5AH-CYCLOHEPTA(5,6)NAPHTHO(2,1-B)FURAN-7-METHANOL, 3B,4,5,6,7,8,9,10,10A,10B,11,12-DODECAHYDRO-7-HYDROXY-10B-METHYL-, (3BS-(3B.ALPHA.,5A.BETA.,7.BETA.,8.BETA.,10A.ALPHA.,10B.BETA.))-
Common Name English
CAFESTEROL
Common Name English
CAFESTOL [MI]
Common Name English
Code System Code Type Description
FDA UNII
AC465T6Q6W
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID3040986
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
MESH
C053400
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
CAS
469-83-0
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
WIKIPEDIA
Cafestol
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
MERCK INDEX
m2907
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY Merck Index
PUBCHEM
108052
Created by admin on Fri Dec 15 18:39:37 UTC 2023 , Edited by admin on Fri Dec 15 18:39:37 UTC 2023
PRIMARY
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