69256-15-1

Basic information

• Product Name: (+)-Leucocyanidin
• Synonyms: (+)-(2R,3S,4R)-3,3',4,4',5,7-Hexahydroxyflavan;(2R,3S,4R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
• CAS NO: 69256-15-1
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.26746
• Mol File: 69256-15-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: >300℃
• Boiling Point: 641.5°C at 760 mmHg
• Flash Point: 341.8°C
• Appearance: /
• Density: 1.709
• Vapor Pressure: 2.46E-17mmHg at 25°C
• Refractive Index: 1.78
• CAS DataBase Reference: (+)-Leucocyanidin(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Leucocyanidin(69256-15-1)
• EPA Substance Registry System: (+)-Leucocyanidin(69256-15-1)

Safety Data

• Hazardous Substances Data: 69256-15-1(Hazardous Substances Data)

Usage

General Description

(+)-Leucocyanidin is a bioactive phytochemical compound that belongs to the class of flavonoids known as anthocyanidins. It is predominantly found in a variety of fruits, vegetables, nuts, seeds, stems, and flowers. (+)-Leucocyanidin exhibits certain properties that offer potential health benefits, including antioxidant, anti-inflammatory, anti-cancer and cardio-protective effects. It also plays a salient role in plant pigmentation, providing a range of colors from red to blue. Additionally, (+)-Leucocyanidin has been studied for its potential in therapeutic applications for various health conditions, indicating its medicinal value.

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 
• 85443-49-8 (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman 
• 574749-29-4 (+)-3',4',3,5,7-penta-O-benzyl-(4S)-hydroxycatechine 
• 478241-14-4 (+)-(4S)-acetoxy-3',4',3,5,7-penta-O-benzylcatechine 
• 574749-31-8 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one 
• 154-23-4 catechin 

Downstream Products

• 35499-74-2 3’,4’,5,7-tetra-O-methyl-4β-hydroxycatechin 
• 87303-89-7 (+)-(2R,3S,4R)-3,4-dihydroxy-5,7,3',4'-tetramethoxyflavan 
• 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 
• 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 
• 93527-39-0 (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan 
• 12798-57-1 [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin 
• 23567-23-9 procyanidin B₃ 
• 25095-06-1 (2R,3S)-2,3-trans-3',4,4',5,7-pentamethoxyflavan-3-ol 

Relevant articles and documents

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.

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.

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.