68200-27-1

Basic information

• Product Name: (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan
• Synonyms: (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan
• CAS NO: 68200-27-1
• Molecular Weight: 700.72
• Mol File: 68200-27-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan(68200-27-1)
• EPA Substance Registry System: (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan(68200-27-1)

Safety Data

• Hazardous Substances Data: 68200-27-1(Hazardous Substances Data)

Upstream product

• 23459-99-6 arecatannin A-1 
• 100-53-8 phenylmethanethiol 
• 37064-30-5 procyanidin C₁ 
• 88057-90-3 C₇₅H₆₀O₃₀ 
• 68178-64-3 epicatechin-(4β<*>8)-epicatechin-(4β<*>2)-phloroglucinol 
• 88847-05-6 epicatechin (4β,8)5-hexamer 
• 86631-39-2 epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin 
• 86631-38-1 (-)-epicatechin-<4β->8>-(-)-epicatechin-<4β->8>-(-)-epicatechin-<4β->8>-(-)-epicatechin 
• 88057-90-3 epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8,2β->O->7)-epicatechin-(4α->8)-epicatechin 
• 126671-46-3 epicatechin-(4β→6)-epicatechin-(4β→8)-epicatechin-(4β→6)-epicatechin 

Relevant articles and documents

PROANTHOCYANIDIN POLYMERS WITH ANTISECRETORY ACTIVITY AND PROANTHOCYANIDIN OLIGOMERS FROM GUAZUMA ULMIFOLIA BARK

Bioassay-guided fractionation of a crude extract of Guazuma ulmifolia bark led to the isolation of polymeric proanthocyanidins which inactivated cholera toxin (CT).The average degree of polymerization (DP) of the active compounds ranged from 14.4 to 32.0.The polymers consisted mainly of (-)-epicatechin units.In polymers of a representative fraction, the flavanol units were connected by 8> bonds and, less frequently, by 6> bonds.Inhibition of CT by tannins increased with Mr and conformation flexibility of the tannin molecule.Several known procyanidin oligomers were also isolated. 1H NMR shift rules to distinguish between 8> and 6> linked proanthocyanidin peracetates, that have been proposed for dimers, were extended to trimers and a tetramer.A further diagnostic shift parameter to determine the interflavanoid bonding position is presented and the conformation of oligomeric proanthocyanidin peracetates is discussed. - Key Word Index: Guazuma ulmifolia; Sterculiaceae; bark; proanthocyanidins; tannins; polymers; gel permeation chromatography; NMR; thiolytic degradation; (-)-epicatechin; peracetates; antisecretory activity.

THIOLYSIS OF BIRCH BARK PROCYANIDINES: STRUCTURAL DEPENDENCE IN FORMATION OF 2,3-CIS-3,4-CIS-FLAVAN-4-BENZYLTHIOETHERS FROM PROCYANIDINS

Thiolytic studies of the birch bark procyanidins, epicatechin-(4β->8)-catechin (B1), epicatechin-(4β->6)-catechin (B7) and epicatechin-(4β->8)-epicatechin-(4β->8)-catechin, provided, in addition to known β-thioethers, evidence for the presence of the first 2,3-cis-3,4-cis-flavan-4-benzylthioethers.Their formation is dependent on the 2,3-stereochemistry of the 'lower' terminal flavan unit and apparently on the relative lability of the interflavanoid linkage.By contrast, epicatechin-(4β->8)-epicatechin (B2), epicatechin-(4β->6)-epicatechin (B5) and epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin (C1), afforded only 2,3-cis-3,4-trans-flavan-4-benzylthioethers.

PROCYANIDIN POLYMERS OF DOUGLAS FIR BARK: STRUCTURE FROM DEGRADATION WITH PHLOROGLUCINOL

Reaction of the condensed tannin polymers of Douglas fir inner bark with phloroglucinol yielded catechin, epicatechin, procyanidin B-2, catechin-(4α->2)-phloroglucinol, epicatechin-(4β->2)-phloroglucinol, the novel compound epicatechin-(4α->2)-phloroglucinol and 1,3-di-(2,4,6-trihydroxyphenyl)-1-(3,4-di-hydroxyphenyl)-propan-2-ol.Also isolated were epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol, epicatechin-(4β->6)-epicatechin-(4β->2)-phloroglucinol, and three other novel phloroglucinol adducts, catechin-(4α->8)-epicatechin-(4β->2)-phloroglucinol, epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol and epicatechin-(4β->6)-epicatechin-(4β->8)-epicatechin-(4β->2)-phloroglucinol.The results suggest that the configuration of the extender units is almost exclusively 2,3-cis, while the terminal units are mixed, with 2,3-cis slightly predominating.The C-4 to C-8 interflavonoid linkage predominates over the C-4 to C-6 linkage by a 4:1 ratio. Key Word Index Pseudotsuga menziesii; Pinaceae; Douglas fir; procyanidin; degradation; phloroglucinol-adducts.