Bergaptol - CAS 486-60-2
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
A natural furanocoumarin extract from lemon and bergamot acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme
Publictions citing BOC Sciences Products
  • >> More
Solid powder
4-hydroxyfuro[3,2-g]chromen-7-one; 4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 4-Hydroxybergapten;
Soluble in DMSO
Store at -20 °C
Antiproliferative and anticancer
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Melting Point:
275-278 °C
Canonical SMILES:
1.Biotransformations of 6',7'-dihydroxybergamottin and 6',7'-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.
Myung K1, Manthey JA, Narciso JA. Bioorg Med Chem Lett. 2012 Mar 15;22(6):2279-82. doi: 10.1016/j.bmcl.2012.01.081. Epub 2012 Jan 30.
Penicillium digitatum, as well as five other citrus pathogenic species, (Penicillium ulaiense Link, Geotrichum citri Link, Botrytis cinerea P. Micheli ex Pers., Lasiodiplodia theobromae (Pat.) Griffon & Maubl., and Phomopsis citri (teleomorph Diaporthe citri)) were observed to convert 6',7'-epoxybergamottin (1) into 6',7'-dihydroxybergamottin (2), bergaptol (3), and an opened lactone ring metabolite 6,7-furano-5-(6',7'-dihydroxy geranyloxy)-2-hydroxy-hydrocoumaric acid (4). Metabolism of 2 by these fungi also proceeded to 4. The structure of 4 was established by high resolution mass spectrometry and (1)H and (13)C NMR techniques. The inhibitory activity of 4 towards human intestinal cytochrome P450 3A4 (CYP3A4) was greatly decreased (IC(50) >172.0 μM) compared to 2 (IC(50)=0.81 μM).
2.Coumarins from Seseli hartvigii.
Zhang L1, Tosun A, Baba M, Okada Y, Wu L, Okuyama T. Nat Prod Commun. 2010 Jul;5(7):1067-70.
Linear-type furocoumarins, 5-[(2"E,6"R)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen and 5-[(2"E,6"S)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen (1) were first isolated from whole plants of Seseli hartvigii together with one new natural product 6-(3'-methyl-2'-oxo-3'-butenyl)-7-methoxycoumarin (2), and four known compounds (tamarin, bergaptol, notoptol, and a mixture of beta-sitosterol and stigmasterol). The structure of 1 was elucidated by extensive spectroscopic analysis and chemical conversion. The modified Mosher's method and HPLC were applied to determine its stereochemistry. Both R- and S-configurations exist in 1; after modification by Mosher's reagent, they were effectively separated, and their ratio was deduced to be 59% and 41%, respectively.
3.Major furocoumarins in grapefruit juice I: levels and urinary metabolite(s).
Messer A1, Nieborowski A, Strasser C, Lohr C, Schrenk D. Food Chem Toxicol. 2011 Dec;49(12):3224-31. doi: 10.1016/j.fct.2011.09.005. Epub 2011 Sep 12.
Furocoumarins are phototoxic and photogenotoxic natural plant constituents occurring in cosmetics, food and drugs. Grapefruit juice is considered as a major dietary source of furocoumarins although few is known about the variability of furocoumarins in grapefruit juice. We analyzed the major furocoumarins in eight commercial grapefruit juices and in freshly prepared juices made from pink grapefruit obtained from German retailers. Bergaptol was the major furocoumarin in commercial juices, followed by bergamottin and 6',7'-dihydroxy-bergamottin (DHB), whereas an inverse picture (DHB>bergamottin>bergaptol) was obtained in freshly prepared juices. Results from different batches of a single brand of commercial juice, purchased over a period of 7 months, revealed a variability of about 50% for the individual furocoumarins and the sum. In a study with healthy volunteers, consumption of 900 ml commercial grapefruit juice (containing 12.5mg bergaptol, 6.
4.Characterization of coumarin-specific prenyltransferase activities in Citrus limon peel.
Munakata R1, Inoue T, Koeduka T, Sasaki K, Tsurumaru Y, Sugiyama A, Uto Y, Hori H, Azuma J, Yazaki K. Biosci Biotechnol Biochem. 2012;76(7):1389-93. Epub 2012 Jul 7.
Coumarins, a large group of polyphenols, play important roles in the defense mechanisms of plants, and they also exhibit various biological activities beneficial to human health, often enhanced by prenylation. Despite the high abundance of prenylated coumarins in citrus fruits, there has been no report on coumarin-specific prenyltransferase activity in citrus. In this study, we detected both O- and C-prenyltransferase activities of coumarin substrates in a microsome fraction prepared from lemon (Citrus limon) peel, where large amounts of prenylated coumarins accumulate. Bergaptol was the most preferred substrate out of various coumarin derivatives tested, and geranyl diphosphate (GPP) was accepted exclusively as prenyl donor substrate. Further enzymatic characterization of bergaptol 5-O-geranyltransferase activity revealed its unique properties: apparent K(m) values for GPP (9 µM) and bergaptol (140 µM) and a broad divalent cation requirement.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related Products

(CAS: 1675821-32-5)

EML-425, a diazinane derivative, has been found to be a CBP/p300 inhibitor that could probably be significant in studies of human leukemia cells. IC50: 1.1 and ...

CAS 69-25-0 Eledoisin

(CAS: 69-25-0)

Eledoisin is an undecapeptide of mollusk origin and it belongs to the tachykinin family of neuropeptides. It was first isolated from the posterior salivary glan...

CAS 115-67-3 paramethadione

(CAS: 115-67-3)

This active molecular is an an antiepileptic and anticonvulsant agent. It is associated with fetal trimethadione syndrome that is also called as paramethadione ...

CAS 435-97-2 Phenprocoumon

(CAS: 435-97-2)

Phenprocoumon, a derivative of coumarin, is known for being an oral anti-coagulant.

CAS 179105-67-0 (Z)-MDL 105519

(Z)-MDL 105519
(CAS: 179105-67-0)

(Z)-MDL 105519 is the inactive isoform of MDL 105519 which is a high affinity NMDA glutamate receptor antagonist at the glycine site.

CAS 4205-90-7 Clonidine

(CAS: 4205-90-7)

Clonidine is an α2-Adrenergic agonist for neuropathic pain.

CAS 944328-88-5 QS11

(CAS: 944328-88-5)

QS11 contains a planar purine ring with C2, C6, and N9-positions substituted. QS11, a GTPase activating protein of ADP-ribosylation factor 1 (ARFGAP1) inhibitor...

CAS 52-21-1 Prednisolone Acetate

Prednisolone Acetate
(CAS: 52-21-1)

Prednisolone Acetate is a synthetic corticosteroid drug that is particularly effective as an immunosuppressant agent.

CAS 4065-45-6 Sulisobenzone

(CAS: 4065-45-6)

Sulisobenzoneis a UV filter which protects the skin from damage by UVB and short-wave UVA ultraviolet light

CAS 129-06-6 Warfarin sodium

Warfarin sodium
(CAS: 129-06-6)

Warfarin is an anticoagulant applicated in the prevention of thrombosis and thromboembolism, the formation of blood clots in the blood vessels and their migrati...

CAS 586357-02-0 O-Desmethyl Mebeverine Acid

O-Desmethyl Mebeverine Acid
(CAS: 586357-02-0)

O-Desmethyl Mebeverine Acid is a metabolite of Mebeverine, which is an antispasmodic.

CAS 147591-46-6 ID-8

(CAS: 147591-46-6)

ID-8 is a DYRK inhibitor, and sustains embryonic stem cell self-renewal in long-term culture.

(CAS: 1044871-04-6)

RVX297 is a BD2 selective inhibitor of BET bromodomains. It is structurally related to the clinical compound RVX-208. It has significant implications on differe...

MK-B 251
(CAS: 40396-69-8)

MK-B 251 is a synthetic bio-active chemical.

CAS 69363-14-0 Schisanhenol

(CAS: 69363-14-0)

Schisanhenol, isolated from Schisandra rubriflora, has antioxidative effect on human LDL oxidation. The mechanism of Schisanhenol against LDL oxidation may be t...

CAS 553-12-8 Protoporphyrin IX

Protoporphyrin IX
(CAS: 553-12-8)

Created by the enzyme protoporphyrinogen oxidase, protoporphyrin IX is an important precursor to biologically essential prosthetic groups.

CAS 532-03-6 Methocarbamol

(CAS: 532-03-6)

Methocarbamol is a central muscle relaxant used to treat skeletal muscle spasms.

CAS 99607-70-2 Cloquintocet-mexyl

(CAS: 99607-70-2)

Cloquintocet-mexyl is a herbicide. It is used to control coarse annual grass of the family poaceae (gramineae). lt was developed by the swiss ciba geigy in the ...

CAS 13647-35-3 Trilostane

(CAS: 13647-35-3)

Trilostane is an inhibitor of 3β-hydroxysteroid dehydrogenase used in the treatment of Cushing’s syndrome.

CAS 33386-08-2 Buspirone hydrochloride

Buspirone hydrochloride
(CAS: 33386-08-2)

Buspirone is a serotonergic (5HT(1A) receptor agonist) anxiolytic drug with some D(2) dopaminergic effect, used for anxiety disorders.

Chemical Structure

CAS 486-60-2 Bergaptol

Quick Inquiry

Verification code

Featured Items