bergaptol

5-hydroxypsoralen

CAS: 486-60-2 C11 H6 O4 MW: 202.16562000

Identification

Namebergaptol
IUPAC4-hydroxyfuro[3,2-g]chromen-7-one
CAS Number486-60-2
FDA UNIIKTC8ANI30F
Molecular FormulaC11 H6 O4
Molecular Weight202.16562000
MDL NumberMFCD00210479
Nikkaji NumberJ12.566K
Beilstein190104

Regulatory

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
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for bergaptol usage levels up tonot for fragrance use.
Recommendation for bergaptol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

bergamot oil orange fruit parsley

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 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].