17654-19-2

Basic information

• Product Name: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one
• Synonyms: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one;(2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS NO: 17654-19-2
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25278
• Mol File: 17654-19-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 577.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.485±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly, Sonicated)
• PKA: 7.52±0.40(Predicted)
• CAS DataBase Reference: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one(17654-19-2)
• EPA Substance Registry System: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one(17654-19-2)

Safety Data

• Hazardous Substances Data: 17654-19-2(Hazardous Substances Data)

Usage

Description

R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one, also known as (R)-Naringenin, is an active flavanone derived from various plant sources, including grape juice. It is a potent inhibitor of cytochromes P450 (CYPs), particularly CYP2C9 and CYP3A. (R)-Naringenin exhibits antioxidative, anti-inflammatory, and antitumorigenic properties, making it a promising compound for various applications in the pharmaceutical and healthcare industries.

Uses

Used in Pharmaceutical Applications:
(R)-Naringenin is used as an inhibitor of cytochromes P450 (CYPs) for its ability to modulate the activity of these enzymes, which are involved in the metabolism of various drugs and endogenous compounds. This property makes it a valuable tool in the development of new drugs and the optimization of drug therapies.
Used in Antioxidant Applications:
(R)-Naringenin is used as an antioxidant due to its ability to neutralize free radicals and protect cells from oxidative stress. This application is particularly relevant in the treatment of conditions associated with increased oxidative stress, such as praquat (PQ)-induced oxidative stress.
Used in Anti-inflammatory Applications:
(R)-Naringenin is used as an anti-inflammatory agent, helping to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Antitumor Applications:
(R)-Naringenin is used in the treatment of praquat (PQ)-induced oxidative stress, where it exhibits antitumorigenic activities. Its potential to inhibit tumor growth and progression makes it a promising candidate for further research and development in cancer therapy.
Used in the Food Industry:
(R)-Naringenin is found in grape juice as rac Naringenin, where it contributes to the health benefits and flavor profile of the product. Its presence in grape juice and other food products highlights its potential as a natural and beneficial compound for human consumption.

Upstream product

• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 1160434-44-5 (2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 
• 25515-46-2 naringenin chalcone 

Downstream Products

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 520-18-3 kaempferol 
• 118333-31-6 (2S,3S)-3,40,5,7-tetrahydroxyflavanone 
• 56297-98-4 (2R,3S)-dihydrokaempferol 
• 56297-98-4 cis-dihydrokaempferol 
• 56297-98-4 trans-dihydrokaempferol 

Relevant articles and documents

Enantiomers of naringenin as pleiotropic, stereoselective inhibitors of cytochrome P450 isoforms

Interactions between naringenin and the cytochrome P450 (CYP) system have been of interest since the first demonstration that grapefruit juice reduced CYP3A activity. The effects of naringenin on other CYP isoforms have been less investigated. In addition

Chiral separation of novel iminonaringenin derivatives

A series of 4-iminonaringenin derivatives 2-6 have been prepared in good overall yields from a condensation reaction between naringenin and primary amines. The structures of all products were confirmed by ultraviolet, infrared, proton nuclear magnetic resonance, and carbon-13 nuclear magnetic resonance spectroscopic techniques. These derivatives were analyzed by high-performance liquid chromatography using polysaccharide-based chiral stationary phases, namely, Chiralpak IB and Chiralcel OD, using various mobile phases. 2-Propanol showed a high enantioselectivity for naringin and its derivatives using achiral column containing immobilized polysaccharides (Chiralpak IB).

Medicinal flowers. xxvii.1) New flavanone and chalcone glycosides, arenariumosides i, ii, iii, and iv, and tumor necrosis factor-α inhibitors from everlasting, flowers of helichrysum arenarium

The methanolic extract from the flowers of Helichrysum arenarium L. Moench was found to show inhibitory effect on tumor necrosis factor-α (TNF-α, 1 ng/ml)-induced cytotoxicity in L929 cells. From the methanolic extract, 50 constituents including four new

Discovery of Novel Bacterial Chalcone Isomerases by a Sequence-Structure-Function-Evolution Strategy for Enzymatic Synthesis of (S)-Flavanones

Chalcone isomerase (CHI) is a key enzyme in the biosynthesis of flavonoids in plants. The first bacterial CHI (CHIera) was identified from Eubacterium ramulus, but its distribution, evolutionary source, substrate scope, and stereoselectivity are still unclear. Here, we describe the identification of 66 novel bacterial CHIs from Genbank using a novel Sequence-Structure-Function-Evolution (SSFE) strategy. These novel bacterial CHIs show diversity in substrate specificity towards various hydroxylated and methoxylated chalcones. The mutagenesis of CHIera according to the substrate binding models of these novel bacterial CHIs resulted in several variants with greatly improved activity towards these chalcones. Furthermore, the preparative scale conversion catalyzed by bacterial CHIs has been performed for five chalcones and revealed (S)-selectivity with up to 96 % ee, which provides an alternative biocatalytic route for the synthesis of (S)-flavanones in high yields.