Bergaptol

Modify Date: 2024-01-04 13:37:30

Bergaptol Structure
Bergaptol structure
Common Name Bergaptol
CAS Number 486-60-2 Molecular Weight 202.163
Density 1.5±0.1 g/cm3 Boiling Point 311.9±11.0 °C at 760 mmHg
Molecular Formula C11H6O4 Melting Point 287-290ºC
MSDS Chinese USA Flash Point 142.4±19.3 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Bergaptol


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]

 Names

Name bergaptol
Synonym More Synonyms

 Bergaptol 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
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.

 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
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

~85%

Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Bellevue III, Frank H.; Woster, Patrick M.; Edwards, David J.; He, Kan; Hollenberg, Paul F. Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 20 p. 2593 - 2598

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Kozawa; Fukumoto; Matsuyama; Baba Chemical and Pharmaceutical Bulletin, 1983 , vol. 31, # 8 p. 2712 - 2717

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Kozawa; Fukumoto; Matsuyama; Baba Chemical and Pharmaceutical Bulletin, 1983 , vol. 31, # 8 p. 2712 - 2717

~%

Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: El-Tawil, B.A.H.; Baghlaf, A.O.; Barbood, S.O. Pharmazie, 1980 , vol. 35, # 8 p. 503

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Gu; Zhang; Yang; Hattori; Namba Chemical and Pharmaceutical Bulletin, 1990 , vol. 38, # 9 p. 2498 - 2502

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Abyshev, A. Z.; Abyshev, D. Z. Chemistry of Natural Compounds, 1983 , vol. 19, # 6 p. 668 - 672 Khimiya Prirodnykh Soedinenii, 1983 , # 6 p. 704 - 709

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Cesar, Thais B.; Manthey, John A.; Myung, Kyung Journal of Natural Products, 2009 , vol. 72, # 9 p. 1702 - 1704

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Bergaptol Structure

Bergaptol

CAS#:486-60-2

Literature: Spaeth; Kainrath Chemische Berichte, 1937 , vol. 70, p. 2274

 Articles1

More 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...

 Synonyms

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
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