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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 59.00 to 61.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 503.00 to 504.00 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 497.00 °F. TCC ( 258.40 °C. ) (est)
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| logP (o/w): | 5.382 (est) |
| Soluble in: |
| | alcohol | | | water, 0.034 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for bergamottin usage levels up to: | | | not for fragrance use.
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| Recommendation for bergamottin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
| | 4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5471349 |
| Pubchem (sid): | 135075729 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | bergamotin | | | bergamotine | | 4-{[(2E)-3,7- | dimethyl-2,6-octadien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one | | (E)-4-((3,7- | dimethyl-2,6-octadienyl)oxy)-7H-furo(3,2-g)(1)benzopyran-7-one | | 4-([(2E)-3,7- | dimethyl-2,6-octadienyl]oxy)-7h-furo[3,2-g]chromen-7-one | | 4-{[(2E)-3,7- | dimethyl-2,6-octadienyl]oxy}-7H-furo[3,2-g]chromen-7-one | | 4-{[(2E)-3,7- | dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one | | 4-[(2E)-3,7- | dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one | | 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- | geranoxypsoralen | | 5- | geranyloxypsoralen | | 5- | geranyl oxypsoralen |
Articles:
| 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. |
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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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3D/inchi