EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

bergaptol
5-hydroxypsoralen

Supplier Sponsors

Name:4-hydroxyfuro[3,2-g]chromen-7-one
CAS Number: 486-60-2Picture of molecule3D/inchi
FDA UNII: KTC8ANI30F
Nikkaji Web:J12.566K
Beilstein Number:190104
MDL:MFCD00210479
XlogP3-AA:2.00 (est)
Molecular Weight:202.16562000
Formula:C11 H6 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
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 280.00 to 282.00 °C. @ 760.00 mm Hg
Boiling Point: 311.00 to 312.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000299 mmHg @ 25.00 °C. (est)
Flash Point: 288.00 °F. TCC ( 142.40 °C. ) (est)
logP (o/w): 1.405 (est)
Soluble in:
 alcohol
 water, 7279 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Bergaptol 98%
BOC Sciences
For experimental / research use only.
Bergaptol ≥95%
Odor: characteristic
Use: A natural furanocoumarin extract from lemon and bergamot acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme Antiproliferative and anticancer
Carbosynth
For experimental / research use only.
Bergaptol
Coompo
For experimental / research use only.
Bergaptol from Plants ≥96%
ExtraSynthese
For experimental / research use only.
Bergaptol (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Bergaptol
Sigma-Aldrich
For experimental / research use only.
Bergaptol
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
 
Pictogram
 
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:
Category:
natural substances and extractives
Recommendation for bergaptol usage levels up to:
 not for fragrance use.
 
Recommendation for bergaptol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280371
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-hydroxyfuro[3,2-g]chromen-7-one
Chemidplus:0000486602
 
References:
 4-hydroxyfuro[3,2-g]chromen-7-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280371
Pubchem (sid):135023642
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00758
HMDB (The Human Metabolome Database):HMDB13679
FooDB:FDB002543
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bergamot oil
Search Trop Picture
 orange fruit
Search Trop Picture
 parsley
Search Trop Picture
 
Synonyms:
7H-furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy-
7H-furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-
4-hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one
4-hydroxy-7H-furo[3,2-g]chromen-7-one
5-hydroxyfuranocoumarin
4-hydroxyfuro[3,2-g]chromen-7-one
5-hydroxypsoralen
 

Articles:

PubMed:[Chemical constituents contained in seeds of Notopterygium franchetii].
PubMed:Characterization of coumarin-specific prenyltransferase activities in Citrus limon peel.
PubMed:Effect of maturity, processing, and storage on the furanocoumarin composition of grapefruit and grapefruit juice.
PubMed:Biotransformations of 6',7'-dihydroxybergamottin and 6',7'-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.
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:Coumarins from Seseli hartvigii.
PubMed:Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry.
PubMed:Notopterygium forbesii Boiss extract and its active constituent phenethyl ferulate attenuate pro-inflammatory responses to lipopolysaccharide in RAW 264.7 macrophages. A "protective" role for oxidative stress?
PubMed:Notopterygium forbesii boiss extract and its active constituents increase reactive species and heme oxygenase-1 in human fetal hepatocytes: mechanisms of action.
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:Constitutive expression of bergaptol O-methyltransferase in Glehnia littoralis cell cultures.
PubMed:Toxical effect of Peganum harmala L. leaves on the cotton leaf worm, Spodoptera littoralis Boisd and its parasitoids Microplitis rufiventris Kok.
PubMed:[Contents of furanocoumarins in grapefruit juice and health foods].
PubMed:White and colored grapefruit juice produce similar pharmacokinetic interactions.
PubMed:[A new coumarin glycoside from Glehnia littoralis].
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:Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae).
PubMed:Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit.
PubMed:The use of heat treatment to eliminate drug interactions due to grapefruit juice.
PubMed:Metabolism of bergamottin by cytochromes P450 2B6 and 3A5.
PubMed:UV-irradiated grapefruit juice loses pharmacokinetic interaction with nifedipine in rats.
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: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:Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase.
PubMed:Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae).
PubMed:Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats.
PubMed:Furanocoumarins from the aerial parts of Dorstenia contrajerva.
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:Photooxygenation of some potentially skin-photosensitizing hydroxyfurocoumarins. Part 2: Xanthotoxol and bergaptol.
PubMed:Differential wound activation of members of the phenylalanine ammonia-lyase and 4-coumarate:CoA ligase gene families in various organs of parsley plants.
PubMed:Isolation of two new coumarin glycosides from Notopterygium forbesii and evaluation of a Chinese crude drug, qiang-huo, the underground parts of N. incisum and N. forbesii, by high-performance liquid chromatography.
PubMed:Temporal and Spatial Patterns of Gene Expression around Sites of Attempted Fungal Infection in Parsley Leaves.
PubMed:Differential regulation and tissue-specific distribution of enzymes of phenylpropanoid pathways in developing parsley seedlings.
PubMed:Biosynthesis of psoralens. Psoralen 5-monooxygenase activity from elicitor-treated Ammi majus cells.
PubMed:Cellular localization of nonhost resistance reactions of parsley (Petroselinum crispum) to fungal infection.
PubMed:Occurrence of phytoalexins and other putative defense-related substances in uninfected parsley plants.
PubMed:Separation of the S-adenosylmethionine: 5- and 8-hydroxyfuranocoumarin O-methyltransferases of Ruta graveolens L. by general ligand affinity chromatography.
PubMed:[Bergaptol ethers].
 
Notes:
skin-photosensitizing hydroxyfurocoumarin. Present in various citrus spp.
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