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cafestol
5a,8-5a,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,5aS,7R,8R,10aR,10bS)-

Supplier Sponsors

CAS Number: 469-83-0Picture of molecule3D/inchi
FDA UNII: AC465T6Q6W
Nikkaji Web:J10.130C
MDL:MFCD01075769
XlogP3-AA:3.30 (est)
Molecular Weight:316.44076000
Formula:C20 H28 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 468.00 to 469.00 °C. @ 760.00 mm Hg (est)
Flash Point: 459.00 °F. TCC ( 237.20 °C. ) (est)
logP (o/w): 4.234 (est)
Soluble in:
 water, 1.595 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Cafestol ≥98%
Santa Cruz Biotechnology
For experimental / research use only.
Cafestol ≥98%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for cafestol usage levels up to:
 not for fragrance use.
 
Recommendation for cafestol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :108052
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0000469830
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):108052
Pubchem (sid):135065388
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09066
HMDB (The Human Metabolome Database):HMDB35710
FooDB:FDB014432
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 coffee
PbMd Search PMC Picture
 coffee bean
Search Trop Picture
 
Synonyms:
(3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-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-ol
5a,8-5a,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,5aS,7R,8R,10aR,10bS)-
 

Articles:

PubMed:Microwave-assisted extraction of green coffee oil and quantification of diterpenes by HPLC.
PubMed:Total synthesis of (±)-cafestol: a late-stage construction of the furan ring inspired by a biosynthesis strategy.
PubMed:Coffee: biochemistry and potential impact on health.
PubMed:Screening of natural compounds as activators of the keap1-nrf2 pathway.
PubMed:Optimization of the isolation and quantitation of kahweol and cafestol in green coffee oil.
PubMed:Looking into individual coffee beans during the roasting process: direct micro-probe sampling on-line photo-ionisation mass spectrometric analysis of coffee roasting gases.
PubMed:Green coffee oil analysis by high-resolution nuclear magnetic resonance spectroscopy.
PubMed:Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP).
PubMed:Microwave-assisted methanolysis of green coffee oil.
PubMed:Dietary modification of metabolic pathways via nuclear hormone receptors.
PubMed:Authentication of Italian Espresso coffee blends through the GC peak ratio between kahweol and 16-O-methylcafestol.
PubMed:Coffee attenuates fibrosis by decreasing the expression of TGF-β and CTGF in a murine model of liver damage.
PubMed:Natural diterpenes from coffee, cafestol and kahweol induce apoptosis through regulation of specificity protein 1 expression in human malignant pleural mesothelioma.
PubMed:Antiangiogenic properties of cafestol, a coffee diterpene, in human umbilical vein endothelial cells.
PubMed:What is it about coffee? Research is showing benefits for everything from depression to liver disease. Is it just the caffeine?
PubMed:Cafestol, a coffee-specific diterpene, induces peripheral antinociception mediated by endogenous opioid peptides.
PubMed:Cholesterol-raising diterpenes in types of coffee commonly consumed in Singapore, Indonesia and India and associations with blood lipids: a survey and cross sectional study.
PubMed:Coffee and its consumption: benefits and risks.
PubMed:Cafestol, a coffee-specific diterpene, induces apoptosis in renal carcinoma Caki cells through down-regulation of anti-apoptotic proteins and Akt phosphorylation.
PubMed:Coffee induces expression of glucuronosyltransferases by the aryl hydrocarbon receptor and Nrf2 in liver and stomach.
PubMed:Decaffeinated coffee and nicotine-free tobacco provide neuroprotection in Drosophila models of Parkinson's disease through an NRF2-dependent mechanism.
PubMed:Absorption, distribution, and biliary excretion of cafestol, a potent cholesterol-elevating compound in unfiltered coffees, in mice.
PubMed:Cafestol, a coffee-specific diterpene, is a novel extracellular signal-regulated kinase inhibitor with AP-1-targeted inhibition of prostaglandin E2 production in lipopolysaccharide-activated macrophages.
PubMed:16-O-Methyl-cafestol.
PubMed:Evaluation of kahweol and cafestol in coffee tissues and roasted coffee by a new high-performance liquid chromatography methodology.
PubMed:Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring-opening pathways.
PubMed:Coffee and liver diseases.
PubMed:The role of epoxidation and electrophile-responsive element-regulated gene transcription in the potentially beneficial and harmful effects of the coffee components cafestol and kahweol.
PubMed:The multifaceted mechanisms for coffee's anti-tumorigenic effect on liver.
PubMed:A perception on health benefits of coffee.
PubMed: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.
PubMed:Effects of coffee and its chemopreventive components kahweol and cafestol on cytochrome P450 and sulfotransferase in rat liver.
PubMed:Protective effects of kahweol and cafestol against hydrogen peroxide-induced oxidative stress and DNA damage.
PubMed:Hepatoprotective and antioxidant effects of the coffee diterpenes kahweol and cafestol on carbon tetrachloride-induced liver damage in mice.
PubMed:The cholesterol-raising factor from coffee beans, cafestol, as an agonist ligand for the farnesoid and pregnane X receptors.
PubMed:Tricalysiamides A-D, diterpenoid alkaloids from Tricalysia dubia.
PubMed:Coffee consumption protects human lymphocytes against oxidative and 3-amino-1-methyl-5H-pyrido[4,3-b]indole acetate (Trp-P-2) induced DNA-damage: results of an experimental study with human volunteers.
PubMed:Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies.
PubMed:[Negligible amounts of cholesterol-raising diterpenes in coffee made with coffee pads in comparison with unfiltered coffee].
PubMed:Coffee and health: a review of recent human research.
PubMed:Modification of N-acetyltransferases and glutathione S-transferases by coffee components: possible relevance for cancer risk.
PubMed:Coffee consumption induces GSTP in plasma and protects lymphocytes against (+/-)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide induced DNA-damage: results of controlled human intervention trials.
PubMed:Coffee oil consumption increases plasma levels of 7alpha-hydroxy-4-cholesten-3-one in humans.
PubMed:Coffee consumption and human health--beneficial or detrimental?--Mechanisms for effects of coffee consumption on different risk factors for cardiovascular disease and type 2 diabetes mellitus.
PubMed: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).
PubMed:Potential chemoprotective effects of the coffee components kahweol and cafestol palmitates via modification of hepatic N-acetyltransferase and glutathione S-transferase activities.
PubMed:CYP7A1 A-278C polymorphism affects the response of plasma lipids after dietary cholesterol or cafestol interventions in humans.
PubMed:Coffee bean extracts rich and poor in kahweol both give rise to elevation of liver enzymes in healthy volunteers.
PubMed:Suppressive effects of the kahweol and cafestol on cyclooxygenase-2 expression in macrophages.
PubMed:Reproducibility of the serum lipid response to coffee oil in healthy volunteers.
PubMed:Coffee diterpenes prevent benzo[a]pyrene genotoxicity in rat and human culture systems.
PubMed:Enhancement of glutathione and g-glutamylcysteine synthetase, the rate limiting enzyme of glutathione synthesis, by chemoprotective plant-derived food and beverage components in the human hepatoma cell line HepG2.
PubMed: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.
PubMed:Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity.
PubMed:Enhancement of the chemoprotective enzymes glucuronosyl transferase and glutathione transferase in specific organs of the rat by the coffee components kahweol and cafestol.
PubMed:The coffee components kahweol and cafestol induce gamma-glutamylcysteine synthetase, the rate limiting enzyme of chemoprotective glutathione synthesis, in several organs of the rat.
PubMed:Elevation of glutathione levels by coffee components and its potential mechanisms.
PubMed:Genetic polymorphisms and lipid response to dietary changes in humans.
PubMed:Protective effects of coffee diterpenes against aflatoxin B1-induced genotoxicity: mechanisms in rat and human cells.
PubMed: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.
PubMed:Apoprotein E genotype and the response of serum cholesterol to dietary fat, cholesterol and cafestol.
PubMed:The coffee diterpene cafestol increases plasma triacylglycerol by increasing the production rate of large VLDL apolipoprotein B in healthy normolipidemic subjects.
PubMed:The hypercholesterolemic effect of cafestol in coffee oil in gerbils and rats.
PubMed:Consumption of French-press coffee raises cholesteryl ester transfer protein activity levels before LDL cholesterol in normolipidaemic subjects.
PubMed:[Coffea arabica--production, botanical classification, new components and active agents and their pharmacological effects].
PubMed:Cafestol increases serum cholesterol levels in apolipoprotein E*3-Leiden transgenic mice by suppression of bile acid synthesis.
PubMed:Unfiltered coffee increases plasma homocysteine concentrations in healthy volunteers: a randomized trial.
PubMed:Effect of coffee oil and its unsaponifiable fraction on plasma cholesterol level in female rats.
PubMed:Validity of animal models for the cholesterol-raising effects of coffee diterpenes in human subjects.
PubMed:Differences between men and women in the response of serum cholesterol to dietary changes.
PubMed:Rapid analysis of cholesterol-elevating compounds in coffee brews by off-line high-performance liquid chromatography/high-resolution gas chromatography.
PubMed:Coffee, alcohol, and the liver.
PubMed:Effects of chemoprotective agents on the metabolic activation of the carcinogenic arylamines PhIP and 4-aminobiphenyl in human and rat liver microsomes.
PubMed:Possible mechanisms underlying the cholesterol-raising effect of the coffee diterpene cafestol.
PubMed:Absorption and urinary excretion of the coffee diterpenes cafestol and kahweol in healthy ileostomy volunteers.
PubMed:The coffee-specific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism.
PubMed:Effect of a coffee lipid (cafestol) on cholesterol metabolism in human skin fibroblasts.
PubMed:Cancer chemoprevention from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazol[4,5-b]pyridine: reconsideration of the evidence.
PubMed:Cafestol, the cholesterol-raising factor in boiled coffee, suppresses bile acid synthesis by downregulation of cholesterol 7 alpha-hydroxylase and sterol 27-hydroxylase in rat hepatocytes.
PubMed:Effect of coffee lipids (cafestol and kahweol) on regulation of cholesterol metabolism in HepG2 cells.
PubMed:Cafestol (a coffee lipid) decreases uptake of low-density lipoprotein (LDL) in human skin fibroblasts and liver cells.
PubMed:The cholesterol-raising diterpenes from coffee beans increase serum lipid transfer protein activity levels in humans.
PubMed:Diterpenes from coffee beans decrease serum levels of lipoprotein(a) in humans: results from four randomised controlled trials.
PubMed:Analysis of the content of the diterpenes cafestol and kahweol in coffee brews.
PubMed:Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat.
PubMed:Separate effects of the coffee diterpenes cafestol and kahweol on serum lipids and liver aminotransferases.
PubMed:The cholesterol-raising factor from coffee beans.
PubMed:Comparison of effect of cafetière and filtered coffee on serum concentrations of liver aminotransferases and lipids: six month randomised controlled trial.
PubMed:The cholesterol-raising factor from coffee beans.
PubMed:Placental glutathione S-transferase (GST-P) induction as a potential mechanism for the anti-carcinogenic effect of the coffee-specific components cafestol and kahweol.
PubMed:Boiled coffee fails to raise serum cholesterol in hamsters and rats.
PubMed:Intake levels, sites of action and excretion routes of the cholesterol-elevating diterpenes from coffee beans in humans.
PubMed:Consumption of unfiltered coffee brews in elderly Europeans. SENECA Investigators.
PubMed:Effect of a coffee lipid (cafestol) on regulation of lipid metabolism in CaCo-2 cells.
PubMed:Coffee oil consumption does not affect serum cholesterol in rhesus and cebus monkeys.
PubMed:Diterpene composition of oils from Arabica and Robusta coffee beans and their effects on serum lipids in man.
PubMed:A placebo-controlled parallel study of the effect of two types of coffee oil on serum lipids and transaminases: identification of chemical substances involved in the cholesterol-raising effect of coffee.
PubMed:Coffee, tea and coronary heart disease.
PubMed:Effects of cafestol and kahweol from coffee grounds on serum lipids and serum liver enzymes in humans.
PubMed:Identity of the cholesterol-raising factor from boiled coffee and its effects on liver function enzymes.
PubMed:End of the coffee mystery: diterpene alcohols raise serum low-density lipoprotein cholesterol and triglyceride levels.
PubMed:Kahweol and cafestol: inhibitors of hamster buccal pouch carcinogenesis.
PubMed:Effects of inducers of drug metabolism on basic hepatic forms of mouse glutathione transferase.
PubMed:Inhibition of hamster buccal pouch carcinogenesis by green coffee beans.
PubMed:Effects of derivatives of kahweol and cafestol on the activity of glutathione S-transferase in mice.
PubMed:Characterization of bacterial mutagenicity mediated by 13-hydroxy-ent-kaurenoic acid (steviol) and several structurally-related derivatives and evaluation of potential to induce glutathione S-transferase in mice.
PubMed:Use of silver nitrate impregnated silica cartridges in the separation of kahweol and cafestol esters by preparative liquid chromatography.
PubMed:Inhibition of carcinogenesis by some minor dietary constituents.
PubMed:Inhibition of neoplasia by minor dietary constituents.
PubMed:Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione S-transferase activity in the mouse.
PubMed:Effect of feeding coffee and its lipids on regenerating and intact liver.
PubMed:[Biologic tolerance of cafestol in the ovum test].
PubMed:[Contribution to the knowledge of cafestol (cafesterol). I].
 
Notes:
constituent of coffee. Constit. of coffee bean oil. Present in boiled-type coffee beverages. Possesses hypercholesterolaemic activity. Diterpenoid constits. of coffee products are associated with cardiotoxic props. Cafestol is a diterpene molecule present in coffee.
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