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| Names | |
|---|---|
| IUPAC name (2R,3S,4S)-Flavan-3,3′,4,4′,5,7-hexol | |
| Systematic IUPAC name (2R,3S,4S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol | |
| Other names Leucocianidol Leucocianidolum Leucocyanidol Leukocyanidine Procyanidol Resivit Leucoanthocyanidol Vitamin P faktor 3,4-Cyanidiol (2R,3S,4S)-3,4,5,7,4-pentahydroxyflavan | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
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| UNII | |
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| Properties | |
| C15H14O7 | |
| Molar mass | 306.26 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Leucocyanidin is a colorless chemical compound that is a member of the class ofnatural products known asleucoanthocyanidins.
(+)-Leucocyanidin can be synthesized from (+)-dihydroquercetin by reduction withsodium borohydride.[1]
Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3,B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).[2]
Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to producecis-dihydroquercetin,trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.
Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2R,3S)-catechin,NADP+, and H2O to produce 2,3-trans-3,4-cis-leucocyanidin, NADPH, and H+. Its gene expression has been studied in developing grape berries and grapevine leaves.[3] Its activity has also been measured in leaves, flowers, and seeds of the legumesMedicago sativa,Lotus japonicus,Lotus uliginosus,Hedysarum sulfurescens, andRobinia pseudoacacia.[4]
The C-4 stereochemistry of leucocyanidin substrates affectsanthocyanidin synthase (ANS) products. This enzyme is an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase.[5]
Leucoyanidin can be found in these plants:[6]
