bergaptol
5-hydroxypsoralen
Identification
| Name | bergaptol |
| IUPAC | 4-hydroxyfuro[3,2-g]chromen-7-one |
| CAS Number | 486-60-2 |
| FDA UNII | KTC8ANI30F |
| Molecular Formula | C11 H6 O4 |
| Molecular Weight | 202.16562000 |
| MDL Number | MFCD00210479 |
| Nikkaji Number | J12.566K |
| Beilstein | 190104 |
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 Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
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].