5a,8-methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-

CAS: 6894-43-5 C20 H26 O3 MW: 314.42482000

Identification

Namekahweol
CAS Number6894-43-5
FDA UNIISearch
Molecular FormulaC20 H26 O3
Molecular Weight314.42482000
MDL NumberMFCD00171665
Nikkaji NumberJ15.677I

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 476.60 °C. @ 760.00 mm Hg (est)
Flash Point 468.00 °F. TCC ( 242.00 °C. ) (est)
logP (o/w) 3.380 (est)
Soluble in water, 2.502 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for kahweol usage levels up tonot for fragrance use.
Recommendation for kahweol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

coffee bean PbMd

Synonyms

(1S,4S,12S,13R,16R,17R)-17-( hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-ol 5a,8- methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b-decahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)- PubMed: Coffee and liver health. PubMed: Anti-Proliferative Properties of Kahweol in Oral Squamous Cancer Through the Regulation Specificity Protein 1. PubMed: Microwave-assisted extraction of green coffee oil and quantification of diterpenes by HPLC. PubMed: Insights on the antitumor effects of kahweol on human breast cancer: decreased survival and increased production of reactive oxygen species and cytotoxicity. PubMed: Coffee: biochemistry and potential impact on health. PubMed: Screening of natural compounds as activators of the keap1-nrf2 pathway. PubMed: An epidemiological study of the association of coffee with chronic liver disease. 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: Microwave-assisted methanolysis of green coffee oil. 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: The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation. PubMed: What is it about coffee? Research is showing benefits for everything from depression to liver disease. Is it just the caffeine? PubMed: Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene. PubMed: Quantification of the Robusta fraction in a coffee blend via Raman spectroscopy: proof of principle. 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: Melatonin sensitizes Caki renal cancer cells to kahweol-induced apoptosis through CHOP-mediated up-regulation of PUMA. PubMed: Discrimination of green arabica and Robusta coffee beans by Raman spectroscopy. PubMed: Nuclear factor-kappaB/signal transducers and activators of transcription-1-mediated inflammatory responses in lipopolysaccharide-activated macrophages are a major inhibitory target of kahweol, a coffee diterpene. PubMed: Coffee induces expression of glucuronosyltransferases by the aryl hydrocarbon receptor and Nrf2 in liver and stomach. PubMed: The coffee diterpene kahweol sensitizes TRAIL-induced apoptosis in renal carcinoma Caki cells through down-regulation of Bcl-2 and c-FLIP. 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 coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK. 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: Kahweol blocks STAT3 phosphorylation and induces apoptosis in human lung adenocarcinoma A549 cells. PubMed: The multifaceted mechanisms for coffee's anti-tumorigenic effect on liver. PubMed: The coffee diterpene kahweol induces heme oxygenase-1 via the PI3K and p38/Nrf2 pathway to protect human dopaminergic neurons from 6-hydroxydopamine-derived oxidative stress. 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: 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: The coffee diterpene kahweol inhibits tumor necrosis factor-alpha-induced expression of cell adhesion molecules in human endothelial cells. PubMed: Inhibitory effect of the coffee diterpene kahweol on carrageenan-induced inflammation in rats. 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: Chemical discrimination of arabica and robusta coffees by Fourier transform Raman spectroscopy. 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: The coffee diterpene kahweol suppress the inducible nitric oxide synthase expression in macrophages. 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: 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: 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: 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: 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: 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: 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: 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: 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.