69256-15-1

Usage

Uses

Used in Health and Wellness Applications:
(+)-Leucocyanidin is used as a dietary supplement for its antioxidant properties, which help protect the body from oxidative stress and support overall health.
Used in Anti-Inflammatory Applications:
(+)-Leucocyanidin is used as an anti-inflammatory agent, potentially reducing inflammation and alleviating symptoms associated with inflammatory conditions.
Used in Cancer Prevention and Treatment:
(+)-Leucocyanidin is used as a chemopreventive and therapeutic agent, with studies suggesting its potential to inhibit cancer cell growth and induce apoptosis in various types of cancer.
Used in Cardiovascular Health:
(+)-Leucocyanidin is used as a cardio-protective agent, potentially reducing the risk of cardiovascular diseases by improving endothelial function and reducing inflammation.
Used in Food and Beverage Industry:
(+)-Leucocyanidin is used as a natural colorant in food and beverage products, providing a range of colors from red to blue and enhancing the visual appeal of these products.
Used in Cosmetics and Personal Care Products:
(+)-Leucocyanidin is used as an ingredient in cosmetics and personal care products for its antioxidant and anti-inflammatory properties, potentially benefiting skin health and appearance.

InChI:InChI=1/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H/t13-,14+,15-/m1/s1

Upstream product

• 67-56-1 methanol 
• 14613-67-3 (2R^*,3S^*,4R^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol 
• 480-18-2 taxifolin 
• 574749-31-8 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one 
• 478241-14-4 (+)-(4S)-acetoxy-3',4',3,5,7-penta-O-benzylcatechine 
• 574749-29-4 (+)-3',4',3,5,7-penta-O-benzyl-(4S)-hydroxycatechine 
• 85443-49-8 (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman 
• 154-23-4 catechin 

Downstream Products

• 25095-06-1 (2R,3S)-2,3-trans-3',4,4',5,7-pentamethoxyflavan-3-ol 
• 61541-02-4 catechin-(4α->2)-phloroglucinol 
• 78284-51-2 (2R,3S,4S)-2,3-trans-3,4-cis-4-(2,4,6-Trihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol 
• 93527-39-0 (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan 
• 13306-05-3 cyanidin 
• 117-39-5 quercetol 
• 480-18-2 (-)-epitaxifolin 
• 480-18-2 taxifolin 
• 125136-17-6 (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol 
• 87303-89-7 (+)-(2R,3S,4R)-3,4-dihydroxy-5,7,3',4'-tetramethoxyflavan 
• 35499-74-2 3’,4’,5,7-tetra-O-methyl-4β-hydroxycatechin 
• 12798-57-1 [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin 
• 23567-23-9 procyanidin B₃ 

Relevant academic research and scientific papers

Production of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns

(+)-2,3-trans-3,4-cis-Leucocyanidin was produced by acidic epimerization of (+)-2,3-trans-3,4-trans-leucocyanidin synthesized by reduction of (+)-dihydroquercetin with NaBH4, and structures of the two stereoisomers purified by C18- and phenyl-reverse-phase high-performance liquid chromatography (HPLC) were confirmed by NMR spectroscopy. We confirm that only 3,4-cis-leucocyanidin is used by leucoanthocyanidin reductase as substrate. The two stereoisomers are quite stable in aqueous solution at -20 °C. Characterization of the two stereoisomers was also performed using electrospray ionization tandem mass spectrometry (ESI-MS/MS), and we discuss here for the first time the corresponding MS/MS fragmentation pathways, which are clearly distinct. The main difference is that of the mode of dehydration of the 3,4-diol in positive ionization mode, which involves a loss of hydroxyl group at either C3 or C4 for the 3,4-cis isomer but only at C3 for the 3,4-trans isomer. Tandem mass spectrometry therefore proves useful as a complementary methodology to NMR to identify each of the two stereoisomers.

The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity

Anthocyanidin synthase (ANS), an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase, catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins. It has been believed that in vivo the products of ANS are the anthocyanidins. However, in vitro studies on ANS using optically active cis- and trans-leucocyanidin substrates identified cyanidin as only a minor product; instead both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates.

An efficient coversion of catechine into 3,4-trans-leucocyanidin

Catechine was efficiently converted into 3,4-trans-leococyanidin by seven steps involving an acetoxylation at the benzylic position of catechine pentabenzyl ether, followed by hydrolysis, oxidation, deprotection, and stereoselective reduction, successively.

Spectroscopic Properties of Free Phenolic 4-Arylflavan-3-ols as Models for Natural Condensed Tannins

A unique range of free phenolic 4-arylflavan-3-ols consisting of four sets (3',4',5,7-tertrahydroxyflavan-3-ol or its 5-deoxy analogue coupled to phloroglucinol or resorcinol), each composed of three diastereomers (2,3-trans-3,4-trans, 2,3-trans-3,4-cis and 2,3-cis-3,4-trans) were synthesized to assess their spectroscopic properties. 1H and 13C NMR and circular dichroism data are related to selected structural and stereochemical features with a view to modelling natural phenolic oligoflavanoids. - Key words: 4-Arylflavan-3-ols 1H NMR 13C NMR Circular dichroism Condensed tannins

Chemical and enzymatic synthesis of monomeric procyanidins (leucocyanidins or 3′,4′,5,7-tetrahydroxyflavan-3,4-diols) from (2R,3R)-dihydroquercetin

The major product from the reduction of (2R,3R)-dihydroquercetin with sodium borohydride is the 2,3-trans-3,4-trans isomer of leucocyanidin [(2R,3S,4R-3,3′,4,4′,5,7-hexahydroxyflavan] whereas the enzymatic reduction product is the 2,3-trans-3,4-cis isomer [(2R,3S,4S)-3,3′,4,4′,5,7-hexahydroxyflavan]. The 3,4-trans isomer may be partly converted to the 3,4-cis isomer under mild acid conditions. The 3,4-cis isomer is more acid-labile, and more reactive both chemically with thiols and enzymatically with a diol reductase, than the 3,4-trans isomer.

LEUCOCYANIDIN: SYNTHESIS AND PROPERTIES OF (2R,3S,4R)-(+)-3,4,5,7,3',4'-HEXAHYDROXYFLAVAN

An isomer of leucocyanidin, (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan has been synthesized from (+)-taxifolin, isolated in its phenolic form, and characterized by 1H and 13C NMR, and formation of the 5,7,3',4'-tetramethyl ether.Leucocyanidin readily polymerizes in acid solution to form a procyanidin polymer of high MW. - Key Word Index: Leucocyanidin; flavan-3,4-diols; synthesis; polymerization; phytochemical significance.

Synthesis of Condensed Tannins. Part 1. Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols, and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism

Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues.Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects.The sign of high intensity Cotton effects to low wavelength, contributed by aryl chromophores at C-4, may almost invariably be correlated with the absolute configuration at this chiral centre of 2,3-trans-3,4-trans, 2,3-trans-3,4-cis, and 2,3-cis-3,4-trans-isomers.