480-17-1

Basic information

• Product Name: LEUCOCYANIDIN POLYMER
• Synonyms: LEUCOCYANIDIN POLYMER;3,3',4,4',5,7-HEXAHYDROXYFLAVANE (POLYMER);leucocianidol;LEUCOCYANIDOL;2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol;2-(3,4-Dihydroxyphenyl)-3,4,5,7-chromantetrol;2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro;Flavan-3,3',4,4',5,7-hexol
• CAS NO: 480-17-1
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.26746
• Product Categories: Anthocyanins
• Mol File: 480-17-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 641.5 °C at 760 mmHg
• Flash Point: 341.8 °C
• Appearance: /
• Density: 1.709 g/cm³
• Vapor Pressure: 2.46E-17mmHg at 25°C
• Refractive Index: 1.78
• CAS DataBase Reference: LEUCOCYANIDIN POLYMER(CAS DataBase Reference)
• NIST Chemistry Reference: LEUCOCYANIDIN POLYMER(480-17-1)
• EPA Substance Registry System: LEUCOCYANIDIN POLYMER(480-17-1)

Safety Data

• Hazardous Substances Data: 480-17-1(Hazardous Substances Data)

Usage

General Description

Leucocyanidin polymer, also known as proanthocyanidin, is a class of polyphenols found in a wide array of plants, especially fruits, seeds, and bark. These chemicals are characterized by the ability to form large polymers composed of various monomer units, primarily compounds called flavanols. Proanthocyanidins possess potent antioxidant properties, and they also show a range of biological activities that may contribute to health benefits, such as anti-inflammatory, cardio-protective, anti-cancer, and anti-bacterial actions. The structure and properties of leucocyanidin polymers may vary depending on the plant source.

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+/m0/s1

Upstream product

• 480-18-2 taxifolin 

Downstream Products

• 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 
• 125136-17-6 (2R,3S,4R)-2,3-trans-3,4-trans-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol 
• 12798-57-1 [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin 
• 23567-23-9 procyanidin B₃ 
• 51196-37-3 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin 
• 29106-51-2 procyanidin B₄ 
• 12798-57-1 (+)-catechin-4α->6-(-)-epicatechin 
• 23459-99-6 <4,8:4,8>-2,3-trans-3,4-cis:2,3-trans-3,4-trans:2,3-cis-bi-<(+)-catechin>-(-)-epicatechin 
• 79763-29-4 <4,8:4,8:4,8>-all-trans-tri-<(+)-catechin>-(-)-epicatechin 
• 51196-38-4 proanthocyanidin B₄ 
• 196710-32-4 <4,8:4,8>-all-trans:2,3-cis-bi-<(+)-catechin>-(-)-epicatechin 
• 25095-06-1 (2R,3S)-2,3-trans-3',4,4',5,7-pentamethoxyflavan-3-ol 

Relevant articles and documents

Isolation and structure elucidation of tetrameric procyanidins from unripe apples (Malus pumila cv. Fuji) by NMR spectroscopy

Procyanidins are plant secondary metabolites widely consumed and known to have various physiological functions, but their bioavailability and mechanism of action are still unclear especially for larger oligomers. One of the reasons is scarce information about the detailed structure of oligomeric procyanidins. As for apple, structures of procyanidin components larger than trimers are scarcely known. In this study, 11 tetrameric procyanidins including two known compounds were isolated from unripe apples (Malus pumila cv. Fuji) and identified by NMR spectroscopic analysis and phloroglucinol degradation. As a result, the detailed structural diversity of tetrameric procyanidins in apple was established.

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.