Welcome to LookChem.com Sign In|Join Free

CAS

  • or
Bergamottin, also known as Bergaptol, is a natural product found in Citrus hystrix, particularly in grapefruit juice. It is a furanocoumarin compound known for its mechanism-based inactivation of the cytochrome P450 3A4 enzyme, which plays a significant role in the grapefruit juice-drug interaction.

7380-40-7

Post Buying Request

7380-40-7 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

7380-40-7 Usage

Uses

Used in Pharmaceutical Industry:
Bergamottin is used as a mechanism-based inactivator for the cytochrome P450 3A4 enzyme. This application is crucial in the pharmaceutical industry because it contributes to the grapefruit juice-drug interaction, which can affect the metabolism and efficacy of certain medications. By understanding and managing this interaction, healthcare professionals can optimize drug therapy and minimize potential adverse effects.
Additionally, Bergamottin's presence in grapefruit juice may have other health-related applications, such as its potential use in dietary supplements or as a natural remedy for various conditions. However, more research is needed to fully understand its therapeutic potential and safety in these contexts.

Check Digit Verification of cas no

The CAS Registry Mumber 7380-40-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,3,8 and 0 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 7380-40:
(6*7)+(5*3)+(4*8)+(3*0)+(2*4)+(1*0)=97
97 % 10 = 7
So 7380-40-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+

7380-40-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B3943)  Bergamottin  >98.0%(HPLC)

  • 7380-40-7

  • 5mg

  • 928.00CNY

  • Detail
  • Sigma-Aldrich

  • (01338)  Bergamottin  analytical standard

  • 7380-40-7

  • 01338-5MG-F

  • 1,485.90CNY

  • Detail

7380-40-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one

1.2 Other means of identification

Product number -
Other names 5-Geranoxypsoralen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7380-40-7 SDS

7380-40-7Relevant articles and documents

Photo-protective effects of selected furocoumarins on β-pinene, R-(+)-limonene and γ-terpinene upon UV-A irradiation

Bitterling, Hannes,Kammerer, Dietmar R.,Lorenz, Peter,Stintzing, Florian C.,Vetter, Walter

, (2021/11/09)

The effect of furocoumarins on terpene photo-oxidation under UV-A light was investigated. For this purpose, four furocoumarins (8-methoxypsoralen, bergapten, bergaptol, bergamottin) each at a level of 5%, was added to solutions of the terpenes β-pinene, R-(+)-limonene and γ-terpinene in ethanol followed by UV irradiation at 366 nm. Bergaptol and bergamottin were synthesized and fully elucidated by NMR spectroscopy. UV-induced transformation of all terpenes was substantially reduced in the presence of furocoumarins. Best photo-protection was observed for γ-terpinene with the addition of bergaptol, i.e. degradation was reduced by 73% compared to the neat substance over a time period of ten days. Bergamottin (50.2%), bergapten (39.8%) and 8-methoxypsoralen (39.6%) also reduced degradation substantially. The protective effect of bergaptol was even noticeable at low concentrations of 0.1%. The main oxidation product of γ-terpinene was p-cymene. Limonene and β-pinene showed a predominated hydroperoxide formation under UV light which could almost completely prevented in the presence of furocoumarins. The protective effect of furocoumarins was presumably due to energy dissipation as a result of the conversion of high energetic radiation (UV-A) into visible light via fluorescence. Phosphorescence or self-quenching within the triplet state were further mechanisms avoiding reactions of excited furocoumarins with the terpenes under investigation. Hence, the photo-stability of the furocoumarins themselves correlated with the extent of their protective effect on all three terpenes.

Parallel evolution of UbiA superfamily proteins into aromatic O-prenyltransferases in plants

Munakata, Ryosuke,Olry, Alexandre,Takemura, Tomoya,Tatsumi, Kanade,Ichino, Takuji,Villard, Cloé,Kageyama, Joji,Kurata, Tetsuya,Nakayasu, Masaru,Jacob, Florence,Koeduka, Takao,Yamamoto, Hirobumi,Moriyoshi, Eiko,Matsukawa, Tetsuya,Grosjean, Jérémy,Krieger, Célia,Sugiyama, Akifumi,Mizutani, Masaharu,Bourgaud, Frédéric,Hehn, Alain,Yazaki, Kazufumi

, (2021/05/11)

Plants produce ~300 aromatic compounds enzymatically linked to prenyl side chains via C–O bonds. These O-prenylated aromatic compounds have been found in taxonomically distant plant taxa, with some of them being beneficial or detrimental to human health. Although their O-prenyl moieties often play crucial roles in the biological activities of these compounds, no plant gene encoding an aromatic O-prenyltransferase (O-PT) has been isolated to date. This study describes the isolation of an aromatic O-PT gene, CpPT1, belonging to the UbiA superfamily, from grapefruit (Citrus × paradisi, Rutaceae). This gene was shown responsible for the biosynthesis of O-prenylated coumarin derivatives that alter drug pharmacokinetics in the human body. Another coumarin O-PT gene encoding a protein of the same family was identified in Angelica keiskei, an apiaceous medicinal plant containing pharmaceutically active O-prenylated coumarins. Phylogenetic analysis of these O-PTs suggested that aromatic O-prenylation activity evolved independently from the same ancestral gene in these distant plant taxa. These findings shed light on understanding the evolution of plant secondary (specialized) metabolites via the UbiA superfamily.

Natural oxyprenylated coumarins are modulators of melanogenesis

Fiorito, Serena,Epifano, Francesco,Preziuso, Francesca,Cacciatore, Ivana,di Stefano, Antonio,Taddeo, Vito Alessandro,de Medina, Philippe,Genovese, Salvatore

, p. 274 - 282 (2018/05/14)

Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses.

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor

Marumoto, Shinsuke,Miyazawa, Mitsuo

supporting information; experimental part, p. 784 - 788 (2012/03/22)

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC50 value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5- methoxypsoralen (35), 8-geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC50 values 25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4

Row,Brown,Stachulski,Lennard

, p. 1604 - 1610 (2008/02/03)

A number of furanocoumarins isolated from grapefruit juice have been found to inhibit CYP3A4 activity in vitro. In this study, we have designed and synthesised a range of analogues based on bergamottin to investigate the relationship between chemical stru

SYNTHESIS OF SPIRO ORTHO ESTERS, SPIRO ORTHO CARBONATES, AND INTERMEDIATES

-

Page 28-29, (2008/06/13)

Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synt

Synthesis and biological evaluation of 6',7'-dihydroxybergamottin (6,7-DHB, a naturally occurring inhibitor of cytochrome P450 3A4

Bellevue III, Frank H.,Woster, Patrick M.,Edwards, David J.,He, Kan,Hollenberg, Paul F.

, p. 2593 - 2598 (2007/10/03)

The recently isolated inhibitor of cytochrome P450 CYP3A4, 6',7'-dihydroxybergamottin (6,7-DHB), was synthesized by an efficient route that is readily adaptable to the production of analogues. The compound was evaluated as an inhibitor of 3A4 in a purified enzyme preparation, as well as against human liver microsomes and human 3A4 expressed in Escherichia coil membrane. In each case, 6,7-DHB proved to be a potent NADPH- and time dependent inactivator of 3A4.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 7380-40-7