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7380-40-7,MFCD00017409
Catalog No.:AA005KEW

7380-40-7 | Bergamottin

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1mg
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$46.00   $32.00
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5mg
≥98%
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA005KEW
Chemical Name:
Bergamottin
CAS Number:
7380-40-7
Molecular Formula:
C21H22O4
Molecular Weight:
338.3970
MDL Number:
MFCD00017409
SMILES:
CC(=CCOc1c2ccoc2cc2c1ccc(=O)o2)CCC=C(C)C
NSC Number:
710599
Properties
Properties
 
Form:
Solid  
MP:
51-54°C  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
570  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Rotatable Bond Count:
6  
XLogP3:
5.6  

Literature

Title: Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents.

Journal: Molecules (Basel, Switzerland) 20120919

Title: Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120901

Title: Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.

Journal: Journal of food science 20120901

Title: Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120501

Title: Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.

Journal: Bioorganic & medicinal chemistry 20120115

Title: Use of comprehensive screening methods to detect selective human CAR activators.

Journal: Biochemical pharmacology 20111215

Title: Major furocoumarins in grapefruit juice I: levels and urinary metabolite(s).

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111201

Title: Construction of a model to estimate the CYP3A inhibitory effect of grapefruit juice.

Journal: Die Pharmazie 20110701

Title: A refined cytochrome P540 IC₅₀ shift assay for reliably identifying CYP3A time-dependent inhibitors.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110601

Title: Effect of maturity, processing, and storage on the furanocoumarin composition of grapefruit and grapefruit juice.

Journal: Journal of food science 20110501

Title: Inactivation of cytochrome P450 (P450) 3A4 but not P450 3A5 by OSI-930, a thiophene-containing anticancer drug.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110201

Title: Food-drug interactions: grapefruit juice.

Journal: Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20110101

Title: Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix.

Journal: Journal of natural products 20101129

Title: A quantitative high-throughput 96-well plate fluorescence assay for mechanism-based inactivators of cytochromes P450 exemplified using CYP2B6.

Journal: Nature protocols 20100901

Title: Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression.

Journal: Molecular nutrition & food research 20100701

Title: Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4.

Journal: Journal of natural products 20090901

Title: In vitro interactions with repeated grapefruit juice administration--to peel or not to peel?

Journal: Planta medica 20090301

Title: Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.

Journal: Toxicology and applied pharmacology 20081015

Title: Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.

Journal: Journal of clinical biochemistry and nutrition 20080901

Title: White and colored grapefruit juice produce similar pharmacokinetic interactions.

Journal: Die Pharmazie 20080801

Title: [Contents of furanocoumarins in grapefruit juice and health foods].

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20080801

Title: Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats.

Journal: Journal of agricultural and food chemistry 20080625

Title: Aspergillus niger metabolism of citrus furanocoumarin inhibitors of human cytochrome P450 3A4.

Journal: Applied microbiology and biotechnology 20080201

Title: Determination of bergamottin in human plasma after grapefruit juice ingestion by an UPLC/MS/MS method.

Journal: Die Pharmazie 20080201

Title: Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.

Journal: Journal of pharmaceutical sciences 20071001

Title: The use of heat treatment to eliminate drug interactions due to grapefruit juice.

Journal: Biological & pharmaceutical bulletin 20061101

Title: Metabolism of bergamottin by cytochromes P450 2B6 and 3A5.

Journal: The Journal of pharmacology and experimental therapeutics 20060901

Title: Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.

Journal: Bioorganic & medicinal chemistry 20060601

Title: Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4.

Journal: Organic & biomolecular chemistry 20060421

Title: Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies.

Journal: Journal of agricultural and food chemistry 20060111

Title: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.

Journal: Current drug metabolism 20051001

Title: Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20050801

Title: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20050601

Title: The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4: evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5.

Journal: The Journal of pharmacology and experimental therapeutics 20050401

Title: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20050401

Title: Probable interaction of bergamottin and cyclosporine in a lung transplant recipient.

Journal: Transplantation 20050327

Title: Two major grapefruit juice components differ in time to onset of intestinal CYP3A4 inhibition.

Journal: The Journal of pharmacology and experimental therapeutics 20050301

Title: Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants.

Journal: Pharmacogenetics and genomics 20050301

Title: Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.

Journal: Biochemical pharmacology 20050215

Title: Photodynamic and photo-cross-linking potential of bergamottin.

Journal: Die Pharmazie 20050101

Title: Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux.

Journal: British journal of pharmacology 20041201

Title: Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans.

Journal: Clinical pharmacology and therapeutics 20041201

Title: Inhibition of in-vitro simvastatin metabolism in rat liver microsomes by bergamottin, a component of grapefruit juice.

Journal: The Journal of pharmacy and pharmacology 20040801

Title: CYP450 dietary inhibitors attenuate TNF-alpha-stimulated endothelial molecule expression and leukocyte adhesion.

Journal: American journal of physiology. Cell physiology 20040401

Title: Utility of microtiter plate assays for human cytochrome P450 inhibition studies in drug discovery: application of simple method for detecting quasi-irreversible and irreversible inhibitors.

Journal: Drug metabolism and pharmacokinetics 20040201

Title: Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.

Journal: The Journal of biological chemistry 20040109

Title: Time course of recovery of cytochrome p450 3A function after single doses of grapefruit juice.

Journal: Clinical pharmacology and therapeutics 20030801

Title: Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice.

Journal: Clinical pharmacology and therapeutics 20030601

Title: In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20030101

Title: Effects of bergamottin on human and monkey drug-metabolizing enzymes in primary cultured hepatocytes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020901

Title: Earl Grey tea intoxication.

Journal: Lancet (London, England) 20020427

Title: The effect of bergamottin on diazepam plasma levels and P450 enzymes in beagle dogs.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020201

Title: Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation.

Journal: Chemical research in toxicology 20020201

Title: Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine.

Journal: Clinical pharmacology and therapeutics 20020101

Title: Inhibition of P-glycoprotein transport function by grapefruit juice psoralen.

Journal: Pharmaceutical research 20010401

Title: Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats.

Journal: Pharmaceutical research 20010201

Title: Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins.

Journal: Clinical pharmacology and therapeutics 20010101

Title: Olguín-Reyes S, et al. Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Food Chem Toxicol. 2012 Sep;50(9):3094-9.

Title: Wu HJ, et al. Bergamottin isolated from Citrus bergamia exerts in vitro and in vivo antitumor activity in lung adenocarcinoma through the induction of apoptosis, cell cycle arrest, mitochondrial membrane potential loss and inhibition of cell migration and invasion. Oncol Rep. 2016 Jul;36(1):324-32.

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