1151-98-0Relevant academic research and scientific papers
Novel pyrano and vinylphenol adducts of Deoxyanthocyanidins in sorghum sourdough
Bai, Yunpeng,Findlay, Brandon,Sanchez Maldonado, Alma Fernanda,Schieber, Andreas,Vederas, John C.,G?nzle, Michael G.
, p. 11536 - 11546 (2014)
This study determined the fate of deoxyanthocyanidins in sorghum sourdoughs. Sourdoughs prepared from the red sorghum variety Town were fermented with the caffeic acid-decarboxylating strains Lactobacillus plantarum FUA3171 and the decarboxylase negative
A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides
Al Bittar, Sheiraz,Mora, Nathalie,Loonis, Michèle,Dangles, Olivier
, p. 4294 - 4302 (2016/07/06)
This work deals with the chemical synthesis of simple analogs of anthocyanins, the main class of water-soluble natural pigments. Flavylium ions with hydroxyl, methoxyl and β-D-glucopyranosyloxyl substituents at positions 4′ and 7 have been prepared by straightforward chemical procedures. Moreover, the two 3-deoxyanthocyanidins of red sorghum apigeninidin (4′,5,7-trihydroxyflavylium) and luteolinidin (3′,4′,5,7-tetrahydroxyflavylium) were synthesized in a one-step protocol. Attempts to synthesize luteolinidin O-β-D-glucosides resulted in a mixture of the 5-O- and 7-O-regioisomers in low yield. A preliminary study of the 4′-β-D-glucopyranosyloxy-7-hydroxyflavylium and 7-β-D-glucopyranosyloxy-4′-hydroxy-flavylium ions shows that simply changing the glucosidation site can profoundly affect the color intensity and stability.
(±)-Diinsininone: made nature's way
Selenski, Carolyn,Pettus, Thomas R.R.
, p. 5298 - 5307 (2007/10/03)
We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.
A new and convenient one-step synthesis of the natural 3-deoxyanthocyanidins apigeninidin and luteolinidin chlorides from 2,4,6-triacetoxybenzaldehyde
Mas, Thierry
, p. 1878 - 1880 (2007/10/03)
The total synthesis of apigeninidin (1), luteolinidin (2) and 5,7-dihydroxyflavylium (5) chlorides is performed through a one step reaction from an acetylated derivative of a commercial reagent. Condensation reaction between 2,4,6-triacetoxybenzaldehyde and an acetophenone derivative in anhyd methanolic hydrogen chloride provides the 3-deoxyanthocyanidins in high yields.
Use of flavylium type compounds non-substituted in position 3 for dyeing keratinous fibres and compositions containing them
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, (2008/06/13)
The invention concerns the use of flavylium type compounds, non-substituted in position 3, and substituted by at least a hydroxyl or alcoxy radical, in particular Apigenidin, in pure form or in the form of plant extracts containing them, as coloring agent
Chemistryl of Anthocyanin Pigments. 9. UV-Visible Spectrophotometric determination of the Acidity Constants of Apigeninidin and Three Related 3-Deoxyflavinium Salts
Brouillard, R.,Iacobucci, G. A.,Sweeny, J. G.
, p. 7585 - 7590 (2007/10/02)
The equilibrium constants for the structural transformations of some 3-deoxyanthocyanidins in water at 25 deg C have been measured by using the pH-jump method.This method have been described previously.According to their particular substitution patterns, hydroxylated flavinium salts can exist in slightly acidic media in several neutral forms: the quinoidal bases A, the carbinol pseudobase B, and the chalcone pseudobase C.Two of the conpounds investigated, namely 4',5,7-trihydroxyflavinium (apigeninidin) and 4'-methoxy-4-methyl-5,7-dihydroxyflavinium chlorides, exist essentially as a mixture of the three neutral forms A, B, and C, the colored species A being the most abundant.As expected, 4',7-dihydroxyflavinium chloride is stable in the open chalcone structiure C.This result is in a good agreement with the catalytic light effect generally observed for the ring-closure reaction of this species leading to the flavinium cation AH+.Only the monohydroxylated pigment 4'-methoxy-4-methyl-7-hydroxyflavinium chloride is the quinoidal base A perfectly stable, whatever the pH.In contrast to natural anthocyanins, the hydration of the pyrilium ring is less efficient and occurs, therefore, at much higher pH values (pH 5-6).Proton loss from the phenolic acidic hydroxyl groups of the flavinium cation takes place in the usual acidity range (pH 4-5), indicating that these groups are strongly hydrogen bonded to the surrounding water molecules.The chalcone content is much higher than for the anthocyanins, and for 4',7-dihydroxyflavinium chloride for instance, the value for the equilibrium ratio of the chalcone to the carbinol is as high as 20.6.
SYNTHESIS OF ANTHOCYANIDINS-III; TOTAL SYNTHESIS OF APIGENINIDIN AND LUTEOLINIDIN CHLORIDES
Sweeny, J.G.,Iacobucci, G.A.
, p. 1481 - 1484 (2007/10/02)
The 3-deoxyanthocyanidins apigeninidin chloride (6a) and luteolinidin chloride (6b) have been synthesized in good yield through the oxidative decarboxylation of the corresponding 4-carboxyflav-2-enes 7a and 7b.
Method for making 3-deoxyanthocyanidins
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, (2008/06/13)
Method for preparing a 3-deoxy-5-hydroxyanthocyanidin salt having a 4' and/or 7 OH substituent from a corresponding acylated flavanone, by (1) reducing the acylated flavanone in a solvent medium by reaction with an alkali borohydride to form a correspondi
