487-26-3

Basic information

• Product Name: FLAVANONE
• Synonyms: (R,S)-2-Phenyl-chroman-4-one;2,3-dihydro-2-phenyl-4h-1-benzopyran-4-on;2,3-Dihydro-2-phenyl-4H-1-benzopyran-4-one;2-Phenyl-4-chromanone;2-phenylchroman-4-one;4-Flavanone;4H-1-Benzopyran-4-one,2,3-dihydro-2-phenyl-;dl-Flavanone
• CAS NO: 487-26-3
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25
• EINECS: 207-654-8
• Product Categories: Flavanones;Biochemistry;Flavonoids;Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Inhibitors
• Mol File: 487-26-3.mol
• Article Data: 253

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 305.66°C (rough estimate)
• Flash Point: 181.9 °C
• Appearance: Very slightly yellow powder
• Density: 0.90 g/cm3
• Vapor Pressure: 3.6E-06mmHg at 25°C
• Refractive Index: 1.4360 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• BRN: 183227
• CAS DataBase Reference: FLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: FLAVANONE(487-26-3)
• EPA Substance Registry System: FLAVANONE(487-26-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• RTECS: LK6906500
• TSCA: Yes
• Hazardous Substances Data: 487-26-3(Hazardous Substances Data)

Usage

Description

FLAVANONE is a chemical compound belonging to the class of flavanones, which are a type of flavonoid. It is the simplest member of the flavanone class, consisting of a flavan bearing an oxo substituent at position 4. FLAVANONE is a very slightly yellow powder that can be found in various citrus juices and wines. Monitoring its content can be useful in characterizing the authenticity of lemon juice, measuring the adulteration of citrus juices, and identifying the presence of orange juice in fruit drinks. Hesperidin is the major flavanone present in the juices and wines obtained from Robinson, Fremont, and Satsuma mandarins.

Uses

1. Used in Pharmaceutical Industry:
FLAVANONE is used as an impurity reference substance for the analysis and quality control of Propafenone, a medication used to treat certain types of irregular heartbeats.
2. Used in Analytical Chemistry:
FLAVANONE is used in High-Performance Liquid Chromatography (HPLC) coupled to electrospray ion trap mass spectrometric methods for the separation and detection of natural flavonoid aglycones. This application aids in the identification and quantification of flavanones in various samples.
3. Used in Biological Research:
Silibinin, a flavanone, is used in a variety of biological functions, including potential therapeutic applications in the treatment of various diseases.
4. Used in Food Industry:
FLAVANONE is used as a marker for the authenticity and quality of citrus juices, such as lemon juice, orange juice, and other fruit drinks. It helps in measuring the adulteration of these juices and identifying the presence of specific types of juice in mixed fruit drinks.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 241, 1988 DOI: 10.1016/S0040-4039(00)80065-9

InChI:InChI=1/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2/t15-/m1/s1

Upstream product

• 51196-83-9 (2S,4S)-(+)-cis-4-hydroxyflavan 
• 7664-93-9 sulfuric acid 
• 157968-59-7 (S)-3,4-dihydro-2-phenyl-2H-1-benzopyran 
• 351458-84-9 (R)-3-Hydroxy-1-(2-hydroxy-phenyl)-3-phenyl-propan-1-one 
• 487-25-2 cis-4-hydroxyflavan 
• 20755-09-3 (+/-)-cis-flavan-4-ol acetate 
• 475644-97-4 (S)-2,3-dihydro-2-phenylspiro[4H-[1]benzopyran-4,2'-[1,3]dithiane] 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 
• 108-95-2 phenol 
• 936183-32-3 tert-butyl (E)-2-(2-hydroxyphenylcarbonyl)-3-phenylprop-2-enoate 
• 936182-86-4 tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 95-56-7 2-hydroxybromobenzene 
• 100306-33-0 (1R)-3-chloro-1-phenylpropanol 

Downstream Products

• 525-82-6 FLAVONE 
• 577-85-5 3-hydroxyflavone 
• 369386-17-4 (2S,3S)-methyl 2-phenyl-2,3-dihydrobenzofuran-3-carboxylate 
• 55568-97-3 (2R,3R)-3-hydroxyflavanone 
• 369386-24-3 (2S,3R)-3-hydroxymethyl-2-phenyl-2,3-dihydrobenzo[b]furan 
• 369386-19-6 (2S,3R)-2-phenyl-3-p-tosyloxymethyl-2,3-dihydrobenzo[b]furan 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 1481-90-9 2-(3-phenylpropyl)phenol 
• 96790-73-7 (2S,3S)-3-hydroxyflavanone 
• 41886-75-3 (2R,4R)-(-)-cis-4-hydroxyflavan 
• 70460-60-5 2-phenyl-chroman-3,4-dione 
• 141334-33-0 Phenyl-2 oximino-3 chromanone-4 
• 1218-80-0 6-bromoflavone 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 

Relevant articles and documents

Effect of Li on the catalytic activity of MgO for the synthesis of flavanone

We have investigated the effects of Li on the structure, surface basicity and catalytic activity of MgO for the synthesis of flavanone. Introduction of low amounts of Li (i.e., ≤0.1 wt.%) was found to promote the rate of the Claisen-Schmidt condensation reaction, which is the first step in this process. However, at Li loadings above 0.1 wt.% a detrimental effect was observed, due to a concomitant decrease in surface area and increase in MgO crystallite size. A strong correlation was observed between surface-normalized basicity and catalytic activity. The increase in activity at higher levels of surface basicity can be attributed to the increased ability of Li-O- pairs to abstract a proton from the 2′-hydroxyacetophenone reactant, thus facilitating the adsorption and subsequent surface reactions of this molecule.

Mechano-chemical versus co-precipitation for the preparation of Y-modified LDHs for cyclohexene oxidation and Claisen-Schmidt condensations

Y-modified LDHs with atomic Mg2+/(Al3++Y3+) of 3 and Al3+/Y3+ ratios of 0.5, 1 and 1.5 were prepared following two preparation methods, i.e. the co-precipitation and mechano-chemical one. The substitution of Al by Y in the brucite-type layer was less effective for the samples prepared by co-precipitation compared to those prepared via mechano-chemical route. In spite the fact yttrium has a larger ionic radius (0.9?) the structural characterizations of these solids confirmed that the layered structure incorporates part of it in the octahedral positions. Further, the reconstruction of the layered structure after an exposure to water for 1 h was more effective for the solid prepared by co-precipitation. The yttrium modified LDHs showed better catalytic activities for cyclohexene oxidation to the corresponding epoxide than the un-modified LDH sample. Then, mixed oxides derived from yttrium-LDH showed very high conversions and selectivities for the synthesis of chalcone.

The effect of solvents on the heterogeneous synthesis of flavanone over MgO

The effect of several solvents on the heterogeneous synthesis of flavanone from benzaldehyde and 2-hydroxyaceophenone over a solid MgO catalyst was studied experimentally through kinetic and FTIR spectroscopic studies. High boiling point solvents considered were dimethyl sulfoxide, tetralin, mesitylene, benzonitrile, and nitrobenzene. Dimethyl sulfoxide (DMSO) significantly promoted the rates of both steps used in this synthesis, i.e., the Claisen-Schmidt condensation reaction of benzaldehyde with 2-hydroxyacetophenone and the subsequent isomerization of the 2′-hydroxychalcone intermediate to flavanone. The effect was more pronounced for the second reaction. Even the presence of small amounts of DMSO in other solvents, e.g., benzonitrile and nitrobenzene, resulted in strong promotion of the flavanone synthesis scheme. The results of FTIR studies indicated the formation of strongly held surface sulfate species following the interaction of DMSO with the MgO surface. The presence of these sulfate species affected the adsorption behavior of benzaldehyde and 2-hydroxyacetophenone on the surface of the MgO catalyst and led to the formation of surface benzoate species. These differences might be responsible for the observed change in the catalytic behavior of MgO during the synthesis of flavanone in the presence on DMSO.

Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose

In order to develop new type of chiral separation materials, in this study, 6-amino-6-deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6-amino-6-deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high-performance liquid chromatography. The resulted 6-amido-6-deoxyamyloses and amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6-nonphenyl (6-nonPh) CS of amylose 6-cyclohexylformamido-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl-heterogeneous (Ph-hetero) CS of amylose 6-(4-methylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl-homogeneous (Ph-homo) CS of amylose 6-(3,5-dimethylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph-hetero CSs, the enantioselectivity depended on the combination of the substituent at 6-position and that at 2- and 3-positions; as for Ph-homo CSs, the enantioselectivity was related to the substituent at 2-, 3-, and 6-positions; with respect to 6-nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph-hetero and Ph-homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6-position could not provide π–π interactions, the 6-nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph-homo and Ph-hetero CSs.

B regioselective and chemoselective biotransformation of 2′-hydroxychalcone derivatives by marine-derived fungi

Eight fungal strains (Penicillium raistrickii CBMAI 931, Cladosporium sp. CBMAI 1237, Aspergillus sydowii CBMAI 935, Penicillium oxalicum CBMAI 1996, Penicillium citrinum CBMAI 1186, Mucor racemosus CBMAI 847, Westerdykella sp. CBMAI 1679, and Aspergillus sclerotiorum CBMAI 849) mediated the biotransformation of the 2′-hydroxychalcone 1a. The main products obtained were from hydrogenation, hydroxylation, and cyclization reactions. Penicillium raistrickii CBMAI 931 catalyzed the chemoselective reduction of 1a to produce 2′-hydroxydihydrochalcone 2a (72%) in 7 days of incubation in phosphate buffer (pH 7). Aspergillus sydowii CBMAI 935 promoted the hydroxylation of 1a to yield 2′,4-dihydroxy-dihydrochalcone 5a (c = 42%) in 7 days of incubation in phosphate buffer (pH 8). The reaction using P. citrinum CBMAI 1186 and M. racemosus CBMAI 847 presented main cyclization products in phosphate buffer (pH 8), but the reactions with these fungi did not present enantioselectivity. Marine-derived fungi were effective and versatile biocatalysts for biotransformation of the 2′-hydroxychalcones yielding different products according to the conditions and microorganism used.