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CAS Number: 7380-40-7Picture of molecule3D/inchi
Nikkaji Web:J15.428H
Beilstein Number:1353914
XlogP3-AA:5.60 (est)
Molecular Weight:338.40314000
Formula:C21 H22 O4
BioActivity Summary:listing
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
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 59.00 to 61.00 °C. @ 760.00 mm Hg
Boiling Point: 503.00 to 504.00 °C. @ 760.00 mm Hg (est)
Flash Point: 497.00 °F. TCC ( 258.40 °C. ) (est)
logP (o/w): 5.382 (est)
Soluble in:
 water, 0.034 mg/L @ 25 °C (est)
Insoluble in:
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Bergamottin 98%
BOC Sciences
For experimental / research use only.
Bergamottin ≥98%
Odor: characteristic
Use: Bergamottin (5-geranoxypsoralen) is a natural furanocoumarin found in the pulp of pomelos and grapefruits. It is also found in
For experimental / research use only.
Bergamottin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
For experimental / research use only.
analytical standard
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
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:
natural substances and extractives
Recommendation for bergamottin usage levels up to:
 not for fragrance use.
Recommendation for bergamottin 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 :5471349
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5471349
Pubchem (sid):135075729
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
HMDB (The Human Metabolome Database):HMDB33782
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 bergamot oil
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 lemon fruit oil
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 lemon oil
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 lemon pericarp
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 lime fruit
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7H-furo(3,2-g)(1)benzopyran-7-one, 4-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-
7H-furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-
5-geranyl oxypsoralen


PubMed:Bergamottin, a natural furanocoumarin obtained from grapefruit juice induces chemosensitization and apoptosis through the inhibition of STAT3 signaling pathway in tumor cells.
PubMed:Absence of Furanocoumarins in Advantra Z® (Citrus aurantium, Bitter Orange) Extracts.
PubMed:Labeled content of two furanocoumarins in dietary supplements correlates with neither actual content nor CYP3A inhibitory activity.
PubMed:Components of foods inhibit a drug exporter, human multidrug and toxin extrusion transporter 1.
PubMed:Thorough investigation of the oxygen heterocyclic fraction of lime (Citrus aurantifolia (Christm.) Swingle) juice.
PubMed:Comprehensive profiling and marker identification in non-volatile citrus oil residues by mass spectrometry and nuclear magnetic resonance.
PubMed:Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium.
PubMed:Rapid Quantitation of Furanocoumarins and Flavonoids in Grapefruit Juice using Ultra-Performance Liquid Chromatography.
PubMed:Protein sequestration of lipophilic furanocoumarins in grapefruit juice.
PubMed:In vitro inhibition of cytochrome P450 3A4 by Aronia melanocarpa constituents.
PubMed:Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents.
PubMed:Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.
PubMed:Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds.
PubMed:Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test.
PubMed:Effect of maturity, processing, and storage on the furanocoumarin composition of grapefruit and grapefruit juice.
PubMed:Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect.
PubMed:Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
PubMed:Major furocoumarins in grapefruit juice II: phototoxicity, photogenotoxicity, and inhibitory potency vs. cytochrome P450 3A4 activity.
PubMed:Major furocoumarins in grapefruit juice I: levels and urinary metabolite(s).
PubMed:Construction of a model to estimate the CYP3A inhibitory effect of grapefruit juice.
PubMed:The interaction potential of herbal medicinal products: a luminescence-based screening platform assessing effects on cytochrome P450 and its use with devil's claw (Harpagophyti radix) preparations.
PubMed:Food-drug interactions: grapefruit juice.
PubMed:[Furanocoumarins contents and cytochrome P450 3A (CYP3A) inhibitory activities of various processed fruit peel products: outflow of 6',7'-Dihydroxybergamottin during processing treatment of peel].
PubMed:[Flavonoids--bioactive compounds in fruits juice].
PubMed:A quantitative high-throughput 96-well plate fluorescence assay for mechanism-based inactivators of cytochromes P450 exemplified using CYP2B6.
PubMed: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.
PubMed:Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells.
PubMed:Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4.
PubMed:Dose-response relationship for the pharmacokinetic interaction of grapefruit juice with dextromethorphan investigated by human urinary metabolite profiles.
PubMed:Development of a reversed-phase high-performance liquid chromatographic method for analyzing furanocoumarin components in citrus fruit juices and Chinese herbal medicines.
PubMed:[Studies on chemical constituents in roots and rhizomes of Notopterygium incisum].
PubMed:In vitro interactions with repeated grapefruit juice administration--to peel or not to peel?
PubMed:Removal of furanocoumarins in grapefruit juice by edible fungi.
PubMed:Influence of electron-beam irradiation on bioactive compounds in grapefruits ( Citrus paradisi Macf.).
PubMed:Evaluation of flavonoids and furanocoumarins from Citrus bergamia (Bergamot) juice and identification of new compounds.
PubMed:Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.
PubMed:[Contents of furanocoumarins in grapefruit juice and health foods].
PubMed:White and colored grapefruit juice produce similar pharmacokinetic interactions.
PubMed:Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.
PubMed:Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats.
PubMed:Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities.
PubMed:Determination of bergamottin in human plasma after grapefruit juice ingestion by an UPLC/MS/MS method.
PubMed:Aspergillus niger metabolism of citrus furanocoumarin inhibitors of human cytochrome P450 3A4.
PubMed:Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins.
PubMed:Distribution of flavonoids and furocoumarins in juices from cultivars of Citrus bergamia Risso.
PubMed:Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.
PubMed:Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.
PubMed:Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
PubMed:The use of heat treatment to eliminate drug interactions due to grapefruit juice.
PubMed:Impact of citrus soft drinks relative to grapefruit juice on ciclosporin disposition.
PubMed:Metabolism of bergamottin by cytochromes P450 2B6 and 3A5.
PubMed:UV-irradiated grapefruit juice loses pharmacokinetic interaction with nifedipine in rats.
PubMed:Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4.
PubMed:Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.
PubMed:Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies.
PubMed:Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes.
PubMed:[Effects of sweetie juice on nifedipine pharmacokinetics in rats].
PubMed:[Comprehensive determination of furanocoumarin derivatives in citrus juice by high performance liquid chromatography].
PubMed:Distribution of furanocoumarins in grapefruit juice fractions.
PubMed:Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants.
PubMed:Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
PubMed:Probable interaction of bergamottin and cyclosporine in a lung transplant recipient.
PubMed:The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation.
PubMed:Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs.
PubMed:Photodynamic and photo-cross-linking potential of bergamottin.
PubMed:Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.
PubMed: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.
PubMed:Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans.
PubMed:Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4.
PubMed:Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux.
PubMed: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.
PubMed:Two major grapefruit juice components differ in time to onset of intestinal CYP3A4 inhibition.
PubMed:Inhibition of in-vitro simvastatin metabolism in rat liver microsomes by bergamottin, a component of grapefruit juice.
PubMed:Two major grapefruit juice components differ in intestinal CYP3A4 inhibition kinetic and binding properties.
PubMed:Screening of furanocoumarin derivatives in citrus fruits by enzyme-linked immunosorbent assay.
PubMed:Herbal modulation of P-glycoprotein.
PubMed:CYP450 dietary inhibitors attenuate TNF-alpha-stimulated endothelial molecule expression and leukocyte adhesion.
PubMed:Herbal bioactivation: the good, the bad and the ugly.
PubMed:The effects of fruit juices on drug disposition: a new model for drug interactions.
PubMed:Time course of recovery of cytochrome p450 3A function after single doses of grapefruit juice.
PubMed:Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice.
PubMed:Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells.
PubMed:[Grapefruit juice and drugs: a hazardous combination?].
PubMed:In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice.
PubMed:Effects of bergamottin on human and monkey drug-metabolizing enzymes in primary cultured hepatocytes.
PubMed:Earl Grey tea intoxication.
PubMed: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.
PubMed:The effect of bergamottin on diazepam plasma levels and P450 enzymes in beagle dogs.
PubMed:Inhibition of P-glycoprotein transport function by grapefruit juice psoralen.
PubMed:Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats.
PubMed:Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins.
PubMed:Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients.
PubMed:Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells.
PubMed:Effect of furanocoumarin derivatives in grapefruit juice on the uptake of vinblastine by Caco-2 cells and on the activity of cytochrome P450 3A4.
PubMed:Inhibition selectivity of grapefruit juice components on human cytochromes P450.
PubMed:Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation.
PubMed:Isolation of furocoumarins from bergamot fruits as HL-60 differentiation-inducing compounds.
PubMed:Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components.
PubMed:Identification of coumarins from the fruit of Citrus hystrix DC as inhibitors of nitric oxide generation in mouse macrophage RAW 264.7 cells.
PubMed:Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice.
PubMed:Effect of naturally occurring coumarins on the formation of epidermal DNA adducts and skin tumors induced by benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in SENCAR mice.
PubMed:Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in cultured mouse keratinocytes.
PubMed:[Chemical constituents of Notopterygium incisum Ting].
PubMed:Effects of a new psoralen, 5-geranoxypsoralen, plus UVA radiation on murine ATPase positive Langerhans cells.
PubMed:Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins.
PubMed:Psoralens cleave pBR322 DNA under ultraviolet radiation.
PubMed:The photobiological activity of 5-geranoxypsoralen and its photoproducts.
PubMed:Photoreactivity of 5-geranoxypsoralen and lack of photoreaction with DNA.
PubMed:In vitro photostability and photosensitizing properties of bergamot oil. Effects of a cinnamate sunscreen.
constituent of bergamot oil. Constit. of bergamot oil. Also from lemon oil and oils of other Citrus spp. and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6?,7?-dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs.
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