55568-97-3

Upstream product

• 57043-45-5 trans-3-acetoxyflavanone 
• 53074-73-0 2-(2-chloroacetyl)phenol 
• 100-52-7 benzaldehyde 
• 129878-47-3 (E)-2'-hydroxychalcone epoxide 
• 888-12-0 (E)-2'-hydroxy-chalcone 
• 487-26-3 (2S)-flavanone 
• 130796-40-6 (2R,3R)-2,3-dihydroxy-3-phenylpropanoic acid methyl ester 
• 1621-55-2 rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one 
• 487-26-3 Flavanone 
• 149-73-5 trimethyl orthoformate 
• 138610-97-6 4-acetoxy-2-phenyl-2H-1-chromene 
• 94137-50-5 cis-3-hydroxyflavanone dimethyl acetal 
• 25518-22-3 (2-hydroxy-phenyl)-(3-phenyl-oxiranyl)-methanone 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 577-85-5 3-hydroxyflavone 
• 94460-26-1 (+/-)-trans-3-hydroxy-2-phenyl-chroman-4-one semicarbazone 
• 94871-82-6 (+/-)-trans-3-hydroxy-2-phenyl-chroman-4-one-phenylhydrazone 
• 17044-60-9 (+/-)-trans-3-hydroxy-2-phenyl-chroman-4-one oxime 
• 1086-73-3 (2R^*,3S^*,4R^*)-flavan-3,4-diol 
• 57043-45-5 trans-3-acetoxyflavanone 
• 139061-62-4 trans-3-hydroxyflavanone thiosemicarbazone 
• 70188-29-3 trans-2,3-dihydro-3-nosyloxy-2-phenyl-4H-1-benzopyran-4-one 
• 1621-55-2 rac-trans-3-hydroxyflavanone 
• 4940-48-1 rac-2-benzyl-2-hydroxy-2,3-dihydrobenzo[b]furan-3-one 
• 92549-57-0 2-Hydroxy-2-<2-hydroxy-phenyl>-3-phenyl-propionsaeure 
• 487-26-3 Flavanone 
• 139061-55-5 spiro<5-acetamido-3-acetyl-2,3-dihydro-1,3,4-thiadiazole-2,4'-trans-3'-acetoxyflavan> 
• 103165-66-8 (+/-)-3t,4c-Bis-(4-nitro-benzoyloxy)-2r-phenyl-chroman 

Relevant academic research and scientific papers

Production of hydroxlated flavonoids with cytochrome P450 BM3 variant F87V and their antioxidative activities

A variant of P450 BM3 with an F87V substitution [P450 BM3 (F87V)] is a substrate-promiscuous cytochrome P450 monooxygenase. We investigated the bioconversion of various flavonoids (favanones, chalcone, and isoflavone) by using recombinant Escherichia coli cells, which expressed the gene coding for P450 BM3 (F87V), to give their corresponding hydroxylated products. Potent antioxidative activities were observed in some of the products.

Oxidative rearrangement of flavanones with thallium(III) nitrate, lead tetraacetate and hypervalent iodines in trimethyl orthoformate and perchloric or sulfuric acid

An HPLC monitoring protocol has been developed to follow the reaction of flavanone [(±)-1] with thallium(III) nitrate, lead tetracetate, phenyliodonium diacetate (PIDA) or [hydroxyl(tosyloxy)iodo]benzene in trimethyl orthoformate. Besides the major ring-c

Studies towards the stereoselective α-hydroxylation of flavanones. Biosynthetic significance

The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the ?-position, by employing commercially available enantiopure oxaziridines, to afford the desired ?-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds. CSIRO 2008.

Facile epoxidation of α,β-unsaturated ketones with cyclohexylidenebishydroperoxide

Cyclohexylidenebishydroperoxide was successfully used as the oxygen source for the oxidation of α,β-unsaturated ketones for the first time. The corresponding epoxides were obtained in excellent yields under the Weitz-Scheffer reaction conditions.

Synthesis of racemic and enantiomerically enriched α- oxyfunctionalized benzocyclanones and chromanones by dimethyldioxirane and dimethyldioxirane/Mn(III) salen system

Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position α in the whole series. Springer-Verlag 2004.

Synthetic studies towards the preparation of 2-benzyl-2-hydroxybenzofuran- 3(2H)-one, the prototype of naturally occurring hydrated auronols

Various synthetic approaches were employed to prepare 2-benzyl-2- hydroxybenzofuran-3(2H)-one (8), the prototype of naturally occurring auronols. While the base-induced ring transformation of 3-hydroxyflavanone (2) as well as the hydration of 2-benzylidenebenzofuran-3(2H)-one (=aurone; 6) proved to be inappropriate, the hydrogenolytic epoxide-ring opening of 2′- phenylspiro[benzofuran-2(3H),2′-oxiran]-3-one (7), obtained from 6, represents an efficient method to afford the auronol 8.

Lipase-catalyzed kinetic resolution of (+/-)-cis-flavan-4-ol and its acetate: synthesis of chiral 3-hydroxyflavanones.

Lipase-catalyzed kinetic resolution of (+/-)-cis-flavan-4-ol and its acetate led to enantiomerically enriched flavan-4-ol and its acetate. These chiral compounds were converted to (2R, 3R)- and (25, 3S)-3-hydroxyflavanones.

Enantioselective synthetic method for 3-hydroxyflavanones: An approach to (2R,3R)-3',4'-O-dimethyltaxifolin

A new enantioselective synthetic method for (2R,3R)-3-hydroxyflavanone (1a) was developed via asymmetric dihydroxylation (ADH) and intramolecular Mitsunobu reaction as key reactions and the application to synthesis of (2R,3R)-3',4'-O-dimethyltaxifolin (1b) is described. (C) 2000 Elsevier Science Ltd.

Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds

Dimethyldioxirane (DMD), generally as a solution in acetone, has proved itself to be an excellent epoxidising agent. It was observed that either the 2'-hydroxychalcone epoxide or the tans-2,3-dihydroflavonol could be obtained depending on the pH of the reaction mixture and the type of β-arene ring present in the substrate. Using this methodology trans-2,3-dihydroflavonols can be synthesised in far better yields than by the most commonly used method for their synthesis, that of the Algar-Flynn-Oyamada reaction. Treatment of both flavonol 14 and the novel isoaurone 21 with DMD gave unusual products instead of the expected epoxides, but nonetheless, an epoxide was assumed to have formed during the reaction.

Synthesis and cyclization of 1-(2-hydroxyphenyl)-2-propen-1-one epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-hydroxyalkyl)-3-coumaranones

Competitive α and β cyclization of 2'-hydroxychalcone epoxides affords 2-(α-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for α cyclization was observed in the case of β-unsubstituted or -monoalkylated α,β-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the β,β-dimethylated substrates.