Bergaptol is an inhibitor (blocker/antagonist) of debenzylation of the CYP3A4 enzyme with IC50 of 24.92 μM. Recent studies suggest it has antiproliferation and anticancer properties.

Physicochemical Properties

Molecular Formula	C11H6O4
Molecular Weight	202.165
Exact Mass	202.026
CAS #	486-60-2
PubChem CID	5280371
Appearance	Light yellow to yellow solid powder
Density	1.5±0.1 g/cm3
Boiling Point	311.9±11.0 °C at 760 mmHg
Melting Point	287-290ºC
Flash Point	142.4±19.3 °C
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.711
LogP	0.93
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Heavy Atom Count	15
Complexity	312
Defined Atom Stereocenter Count	0
InChi Key	GIJHDGJRTUSBJR-UHFFFAOYSA-N
InChi Code	InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
Chemical Name	4-hydroxyfuro[3,2-g]chromen-7-one
Synonyms	Psoralin, 5-hydroxy- 5-Hydroxypsoralen
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	According to ABTS and DPPH tests, bergaptol (0-800 ppm) exhibits definite activity [1]. In RAW264.7 cells, LPS-induced NO, IL-6, and TNF are inhibited by 50 μg/mL of Bergaptol for 24 hours. Additionally, LPS-induced MAPK phosphorylation and NF-κB activation are inhibited in RAW264.7 cells [3].
ln Vivo	LPS-treated mice's cognitive function is improved when bergamot alcohol (10–40 mg/kg) is administered intraperitoneally once a day, during sleep [Disorder 4].
Cell Assay	Western Blot Analysis[3] Cell Types: Production of LPS--α[3]. Induction of RAW264.7 cells Tested Concentrations: 50 μg/mL Incubation Duration: 24 hrs (hours) Experimental Results: Inhibition of JNK phosphorylation and NF-κB activation. Inhibits the translocation of NF-κB P65 from the cytoplasm to the nucleus.
Animal Protocol	Animal/Disease Models: LPS (40 μg/kg, icv) treated mice [4] ] Doses: 10-40 mg/kg Route of Administration: intraperitoneal (ip) injection, one time/day for two weeks Experimental Results: diminished LPS-induced hippocampal CA1 area nerves Fixation and lysis of metanuclei (H&E staining). Increased dendritic spine density in mice. Inhibits LPS-induced neuroinflammation.
References	[1]. Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit. Bioorganic & Medicinal Chemistry.June 2007, Pages 3684-3691. [2]. Cloning, Functional Characterization, and Catalytic Mechanism of a Bergaptol O-Methyltransferase from Peucedanum praeruptorum Dunn. Front Plant Sci, 2016, 7: 722. [3]. Bergaptol from blossoms of Citrus aurantium L. var. amara Engl inhibits LPS-induced inflammatory responses and ox-LDL-induced lipid deposition. Food Funct. 2020 Jun 24;11(6):4915-4926. [4]. Bergaptol Alleviates LPS-Induced Neuroinflammation, Neurological Damage and Cognitive Impairment via Regulating the JAK2/STAT3/p65 Pathway. J Inflamm Res. 2022 Nov 9;15:6199-6211.
Additional Infomation	Bergaptol is a member of psoralens and a 5-hydroxyfurocoumarin. It is a conjugate acid of a bergaptol(1-). Bergaptol has been reported in Angelica dahurica var. formosana, Dorstenia contrajerva, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 50 mg/mL (~247.33 mM) H2O : ~0.67 mg/mL (~3.31 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (12.37 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.9463 mL	24.7317 mL	49.4633 mL
	5 mM	0.9893 mL	4.9463 mL	9.8927 mL
	10 mM	0.4946 mL	2.4732 mL	4.9463 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.