93602-28-9

Basic information

• Product Name: (+/-)-Naringenin
• Synonyms: TIMTEC-BB SBB006461;5,7,4'-TRIHYDROXYFLAVANONE;5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE;(+/-)-2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE;(+/-)-4',5,7-Trihydroxyflavanone;(+/-)-Naringenin
• CAS NO: 93602-28-9
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25
• EINECS: 266-769-1
• Mol File: 93602-28-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 247-250 °C(lit.)
• Boiling Point: 577.5 °C at 760 mmHg
• Flash Point: 224.7 °C
• Appearance: /
• Density: 1.485 g/cm³
• CAS DataBase Reference: (+/-)-Naringenin(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-Naringenin(93602-28-9)
• EPA Substance Registry System: (+/-)-Naringenin(93602-28-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 93602-28-9(Hazardous Substances Data)

Usage

General Description

Naringenin is a colorless flavanone, a type of flavonoid, that is known for its bitter taste commonly found in grapefruit. The (+/-) in its name denotes the chirality or the spatial arrangement specific to molecules that can exist in mirror-image forms. Classified as an antioxidant, naringenin has been explored for its potential beneficial effects on human health. Research suggests it may have anti-inflammatory, anti-cancer, and neuroprotective properties, but more studies are needed to confirm these benefits. It also influences the metabolism of drugs by inhibiting some cytochrome P450 enzymes, which are involved in the metabolism of certain pharmaceutical drugs in the body.

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

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.

5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one (naringenin): X-ray diffraction structures of the naringenin enantiomers and DFT evaluation of the preferred ground-state structures and thermodynamics for racemization

The R- and S-enantiomers of naringenin were separated by chiral supercritical fluid (SCF) and the absolute configuration of each enantiomer was established by X-ray crystallography. The solid-state data is in agreement with the reported circular dichroism spectra. Both enantiomers crystallize in the monoclinic crystal system in the space group P21 with two independent molecules in the asymmetric unit. In all molecules, the pyrone ring adopts a flattened chair-like conformation in which the C1 atom deviates from the plane drawn through the remaining five atoms of this heterocycle. The 4-hydroxyphenyl substituent located at C1 of the pyrone ring occupies an equatorial position and lies in a plane that is almost perpendicular to the aromatic platform associated with the heterocyclic portion of the molecule. Strong intramolecular O-H?O hydrogen bonding exists between the carbonyl moiety and the aryl hydroxyl group at C5. In both enantiomers, a favorable mutual orientation of two independent molecules promotes the formation of intermolecular O-H?O hydrogen bonds that link them into dimers. There are additional long-range intermolecular O-H?O hydrogen bonds and weak C-H?O contacts within the unit cell of each enantiomer that connect dimers in an extended network. DFT calculations have been performed and the thermodynamics for naringenin racemization via an acyclic chalcone have been computed. Eight energetically accessible conformations have been verified for S-naringenin.

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.