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6894-43-5,MFCD00171665
Catalog No.:AA005MW5

6894-43-5 | Kahweol

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5mg
≥98%
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$123.00   $86.00
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10mg
≥98%
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA005MW5
Chemical Name:
Kahweol
CAS Number:
6894-43-5
Molecular Formula:
C20H26O3
Molecular Weight:
314.4186
MDL Number:
MFCD00171665
SMILES:
OCC1(O)CC23CC1CCC3C1(C(CC2)c2ccoc2C=C1)C
Properties
Computed Properties
 
Complexity:
545  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
3.4  

Literature

Title: The coffee diterpene kahweol suppresses the cell proliferation by inducing cyclin D1 proteasomal degradation via ERK1/2, JNK and GKS3β-dependent threonine-286 phosphorylation in human colorectal cancer cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20160901

Title: Optimization of the isolation and quantitation of kahweol and cafestol in green coffee oil.

Journal: Talanta 20131215

Title: Authentication of Italian Espresso coffee blends through the GC peak ratio between kahweol and 16-O-methylcafestol.

Journal: Food chemistry 20121201

Title: Microwave-assisted methanolysis of green coffee oil.

Journal: Food chemistry 20120915

Title: What is it about coffee? Research is showing benefits for everything from depression to liver disease. Is it just the caffeine?

Journal: Harvard health letter 20120101

Title: The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation.

Journal: Journal of pharmacological sciences 20120101

Title: Functional foods and nutraceuticals in the primary prevention of cardiovascular diseases.

Journal: Journal of nutrition and metabolism 20120101

Title: Natural diterpenes from coffee, cafestol and kahweol induce apoptosis through regulation of specificity protein 1 expression in human malignant pleural mesothelioma.

Journal: Journal of biomedical science 20120101

Title: Quantification of the Robusta fraction in a coffee blend via Raman spectroscopy: proof of principle.

Journal: Journal of agricultural and food chemistry 20110914

Title: Melatonin sensitizes Caki renal cancer cells to kahweol-induced apoptosis through CHOP-mediated up-regulation of PUMA.

Journal: Journal of pineal research 20110501

Title: Coffee and its consumption: benefits and risks.

Journal: Critical reviews in food science and nutrition 20110401

Title: Coffee and caffeine consumption in relation to sex hormone-binding globulin and risk of type 2 diabetes in postmenopausal women.

Journal: Diabetes 20110101

Title: The Nrf2/ARE Pathway: A Promising Target to Counteract Mitochondrial Dysfunction in Parkinson's Disease.

Journal: Parkinson's disease 20110101

Title: Coffee consumption and risk of cancers: a meta-analysis of cohort studies.

Journal: BMC cancer 20110101

Title: 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.

Journal: Nutrition journal 20110101

Title: Molecular and cellular pathways associated with chromosome 1p deletions during colon carcinogenesis.

Journal: Clinical and experimental gastroenterology 20110101

Title: Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene.

Journal: PloS one 20110101

Title: Effects of some common food constituents on cardiovascular disease.

Journal: ISRN cardiology 20110101

Title: Coffee induces expression of glucuronosyltransferases by the aryl hydrocarbon receptor and Nrf2 in liver and stomach.

Journal: Gastroenterology 20101101

Title: 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.

Journal: The Journal of nutritional biochemistry 20100801

Title: Coffee and liver diseases.

Journal: Fitoterapia 20100701

Title: The coffee diterpene kahweol sensitizes TRAIL-induced apoptosis in renal carcinoma Caki cells through down-regulation of Bcl-2 and c-FLIP.

Journal: Chemico-biological interactions 20100607

Title: Evaluation of kahweol and cafestol in coffee tissues and roasted coffee by a new high-performance liquid chromatography methodology.

Journal: Journal of agricultural and food chemistry 20100113

Title: Acanthopanax koreanum fruit waste inhibits lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 in RAW 264.7 macrophages.

Journal: Journal of biomedicine & biotechnology 20100101

Title: 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.

Journal: Biological & pharmaceutical bulletin 20100101

Title: In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids.

Journal: BMC complementary and alternative medicine 20100101

Title: Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring-opening pathways.

Journal: Chemical research in toxicology 20091201

Title: The coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK.

Journal: Apoptosis : an international journal on programmed cell death 20091101

Title: Kahweol blocks STAT3 phosphorylation and induces apoptosis in human lung adenocarcinoma A549 cells.

Journal: Toxicology letters 20090522

Title: Does long-term coffee intake reduce type 2 diabetes mellitus risk?

Journal: Diabetology & metabolic syndrome 20090101

Title: Can coffee prevent caries?

Journal: Journal of conservative dentistry : JCD 20090101

Title: The multifaceted mechanisms for coffee's anti-tumorigenic effect on liver.

Journal: Medical hypotheses 20081101

Title: Cancer is a preventable disease that requires major lifestyle changes.

Journal: Pharmaceutical research 20080901

Title: 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.

Journal: FEBS letters 20080723

Title: A perception on health benefits of coffee.

Journal: Critical reviews in food science and nutrition 20080501

Title: Effects of coffee and its chemopreventive components kahweol and cafestol on cytochrome P450 and sulfotransferase in rat liver.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080401

Title: 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.

Journal: Toxicology and applied pharmacology 20080201

Title: Hepatoprotective and antioxidant effects of the coffee diterpenes kahweol and cafestol on carbon tetrachloride-induced liver damage in mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071101

Title: Protective effects of kahweol and cafestol against hydrogen peroxide-induced oxidative stress and DNA damage.

Journal: Toxicology letters 20070910

Title: 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.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070801

Title: Reduction in antioxidant defenses may contribute to ochratoxin A toxicity and carcinogenicity.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070301

Title: Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies.

Journal: Pharmacological research 20070301

Title: [Negligible amounts of cholesterol-raising diterpenes in coffee made with coffee pads in comparison with unfiltered coffee].

Journal: Nederlands tijdschrift voor geneeskunde 20061230

Title: The coffee diterpene kahweol inhibits tumor necrosis factor-alpha-induced expression of cell adhesion molecules in human endothelial cells.

Journal: Toxicology and applied pharmacology 20061215

Title: Coffee and health: a review of recent human research.

Journal: Critical reviews in food science and nutrition 20060101

Title: Inhibitory effect of green coffee bean extract on fat accumulation and body weight gain in mice.

Journal: BMC complementary and alternative medicine 20060101

Title: Inhibitory effect of the coffee diterpene kahweol on carrageenan-induced inflammation in rats.

Journal: BioFactors (Oxford, England) 20060101

Title: 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.

Journal: Mutation research 20051211

Title: Chemical discrimination of arabica and robusta coffees by Fourier transform Raman spectroscopy.

Journal: Journal of agricultural and food chemistry 20050615

Title: 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).

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050301

Title: 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.

Journal: Molecular nutrition & food research 20050301

Title: Modification of N-acetyltransferases and glutathione S-transferases by coffee components: possible relevance for cancer risk.

Journal: Methods in enzymology 20050101

Title: The coffee diterpene kahweol suppress the inducible nitric oxide synthase expression in macrophages.

Journal: Cancer letters 20040930

Title: Suppressive effects of the kahweol and cafestol on cyclooxygenase-2 expression in macrophages.

Journal: FEBS letters 20040702

Title: Coffee bean extracts rich and poor in kahweol both give rise to elevation of liver enzymes in healthy volunteers.

Journal: Nutrition journal 20040101

Title: Potential chemoprotective effects of the coffee components kahweol and cafestol palmitates via modification of hepatic N-acetyltransferase and glutathione S-transferase activities.

Journal: Environmental and molecular mutagenesis 20040101

Title: Coffee diterpenes prevent benzo[a]pyrene genotoxicity in rat and human culture systems.

Journal: Biochemical and biophysical research communications 20030627

Title: 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.

Journal: Mutation research 20030128

Title: 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.

Journal: Nutrition and cancer 20030101

Title: Reproducibility of the serum lipid response to coffee oil in healthy volunteers.

Journal: Nutrition journal 20030101

Title: Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801

Title: Enhancement of the chemoprotective enzymes glucuronosyl transferase and glutathione transferase in specific organs of the rat by the coffee components kahweol and cafestol.

Journal: Archives of toxicology 20020501

Title: The coffee components kahweol and cafestol induce gamma-glutamylcysteine synthetase, the rate limiting enzyme of chemoprotective glutathione synthesis, in several organs of the rat.

Journal: Archives of toxicology 20020101

Title: Protective effects of coffee diterpenes against aflatoxin B1-induced genotoxicity: mechanisms in rat and human cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010601

Title: Elevation of glutathione levels by coffee components and its potential mechanisms.

Journal: Advances in experimental medicine and biology 20010101

Title: The coffee-specific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism.

Journal: Carcinogenesis 19980801

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