Bergaptol

Bergaptol
Names
	Preferred IUPAC name 4-Hydroxy-7H-furo[3,2-g] [1]benzopyran-7-one
	Other names 5-Hydroxypsoralen, 5-Hydroxyfuranocoumarin
Identifiers
CAS Number	486-60-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444066;
ECHA InfoCard	100.230.572
PubChem CID	5280371;
UNII	KTC8ANI30F ;
CompTox Dashboard (EPA)	DTXSID40197564 ;
	InChI InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H Key: GIJHDGJRTUSBJR-UHFFFAOYSA-N;
	SMILES O=C\1Oc3c(/C=C/1)c(O)c2ccoc2c3;
Properties
Chemical formula	C11H6O4
Molar mass	202.165 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bergaptol is a natural furanocoumarin with the molecular formula C₁₁H₆O₄. It is found in the essential oils of citrus including lemon and bergamot.^[1]

Research

Bergaptol is researched for anti-inflammatory, antioxidant, anti-cancer, anti-osteoporosis, anti-microbial, and anti-lipidemic properties.^[2]

Bergaptol inhibits cytochrome P450 enzymes (CYP), particularly CYP2C9 and CYP3A4. This inhibition can impact the metabolism and concentrations of various drugs and toxins within the body. When compared to other coumarins, bergaptol demonstrates the lowest potency in inhibiting CYP3A4 specifically in cancer cells. Instead, it has the ability to suppress drug efflux transporters, such as P-glycoprotein, which can help overcome chemotherapeutic drug resistance.^[2]

Bergaptol exhibits strong antimicrobial effects and has a high potential for inhibiting quorum sensing, a process crucial for microbial communication and virulence.^[2]

In vivo studies have shown that bergaptol has a longer retention time in plasma compared to other coumarins.^[2]

Toxicity of bergaptol in humans has not been extensively studied and remains unclear.^[2]

Notes

^ Stanley WL, Vannier SH (1957). "Chemical Composition of Lemon Oil. I. Isolation of a Series of Substituted Coumarins". Journal of the American Chemical Society. 79 (13): 3488–3491. doi:10.1021/ja01570a049. ISSN 0002-7863.
^ ^a ^b ^c ^d ^e Phucharoenrak P, Trachootham D (February 2024). "Bergaptol, a Major Furocoumarin in Citrus: Pharmacological Properties and Toxicity". Molecules. 29 (3): 713. doi:10.3390/molecules29030713. PMC 10856120. PMID 38338457.

[StanleyVannier1957-1] Stanley WL, Vannier SH (1957). "Chemical Composition of Lemon Oil. I. Isolation of a Series of Substituted Coumarins". Journal of the American Chemical Society. 79 (13): 3488–3491. doi:10.1021/ja01570a049. ISSN 0002-7863.

[pmid38338457-2] Phucharoenrak P, Trachootham D (February 2024). "Bergaptol, a Major Furocoumarin in Citrus: Pharmacological Properties and Toxicity". Molecules. 29 (3): 713. doi:10.3390/molecules29030713. PMC 10856120. PMID 38338457.

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