Bergaptol

Names

[ CAS No. ]:
486-60-2

[ Name ]:
Bergaptol

[Synonym ]:
4-hydroxyfuranocoumarin
5-Hydroxypsoralen
4-hydroxyfuro[3,2-g]chromen-7-one
4-Hydroxy7H-furo[3,2-g][1]benzopyran-7-one,4-Hydroxybergapten,5-Hydroxy-6,7-furanocoumarin
xanthotoxol
5-Hydroxyfuranocoumarin
7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-
Psoralin,5-hydroxy
4-Hydroxy-7H-furo[3,2-g]chromen-7-one
Bergaptol
9-hydroxyfuranocoumarin

Biological Activity

[Description]:

BergaptolA hydroxylated psoralen that acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 uM. Recent studies suggest that it may have antiproliferative and anticancer properties.target: CYP3A4 [1]IC50: 24.92 [1]For in vivo enzyme activity analysis, 100 μM bergaptol was added to the cultures for an additional 24 h at 37°C. After centrifugation, the supernatant was used to measure the bergapten yield by high performance liquid chromatography (HPLC).[2]

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Natural Products >> Phenylpropanoids

Research Areas >> Cancer

[References]

[1]. Basavaraj Girennavar et al. Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit. Bioorganic & Medicinal Chemistry.June 2007, Pages 3684-3691

[2]. Yucheng Zhao et al. Cloning, Functional Characterization, and Catalytic Mechanism of a Bergaptol O-Methyltransferase from Peucedanum praeruptorum Dunn. Front Plant Sci, 2016, 7: 722.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
311.9±11.0 °C at 760 mmHg

[ Melting Point ]:
287-290ºC

[ Molecular Formula ]:
C₁₁H₆O₄

[ Molecular Weight ]:
202.163

[ Flash Point ]:
142.4±19.3 °C

[ Exact Mass ]:
202.026611

[ PSA ]:
63.58000

[ LogP ]:
0.93

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.711

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Application of the equivalency factor concept to the phototoxicity and –genotoxicity of furocoumarin mixtures

Food Chem. Toxicol. 68 , 257-66, (2014)

• The photo-cytotoxic, -mutagenic, and -clastogenic properties in V79 cells of thirteen furocoumarins (FCs), were analyzed. • Nine FC mixtures including one mixture ‘representing’ FCs in Angelica arch...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.