20194-41-6

Basic information

• Product Name: (-)-Epicatechin-pentaacetate
• Synonyms: (-)-Epicatechin-pentaacetate;(2R)-2α-[3,4-Bis(acetyloxy)phenyl]-3,4-dihydro-2H-1-benzopyran-3α,5,7-triol 3,5,7-triacetate;Epicatechol pentaacetate;(-)-Pentaacetylepicatechin
• CAS NO: 20194-41-6
• Molecular Formula: C₂₅H₂₄O₁₁
• Molecular Weight: 500.45146
• Mol File: 20194-41-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 150-152 °C
• Boiling Point: 624.2 °C at 760 mmHg
• Flash Point: 266.7 °C
• Appearance: /
• Density: 1.38 g/cm³
• CAS DataBase Reference: (-)-Epicatechin-pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Epicatechin-pentaacetate(20194-41-6)
• EPA Substance Registry System: (-)-Epicatechin-pentaacetate(20194-41-6)

Safety Data

• Hazardous Substances Data: 20194-41-6(Hazardous Substances Data)

Usage

General Description

"(-)-Epicatechin-Pentaacetate" is a chemical compound that belongs to the class of organic compounds known as flavonoids. Derived from Epicatechin, it's usually obtained by acetylation, a process where an acetyl group is introduced into a molecule. It can be found in certain plants and its health benefits have been studied across various scientific researches. Some evidence suggests its potential to enhance nitric oxide production, a molecule involved in various physiological and pathological processes, suggesting it may exert cardiovascular protective benefits. (-)-Epicatechin-pentaacetate is also known for its antioxidant properties, which are linked to protecting cells from free radicals. However, it's worth noting that more research is needed to condense its spectrum of benefits and potential uses in medicine or health supplements.

Upstream product

• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 65052-92-8 (+/-)-2,3-trans-3,4-trans-4-hydroxy-3,5,7,3',4'-pentaacetoxyflavan 
• 6685-67-2 (+/-)-taxifolin pentaacetate 
• 154-23-4 (+/-)-epicatechin 
• 7295-85-4 catechin 
• 132400-73-8 (+/-)-catechin 3,7,3',4'-tetraacetate 
• 154-23-4 catechin 
• 154-23-4 (-)-catechin 
• 154-23-4 catechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 

Downstream Products

• 528-58-5 cyanidin chloride 
• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 104263-86-7 ent-catechin 3',4',5,7-tetra-O-methyl ether 
• 19611-22-4 3',4',5,7-tetra-O-methylcatechin 
• 853687-38-4 5,7,3’,4’-O-tetra-tert-butyldimethylsilylepicatechin 
• 1071725-98-8 3,7,4'-triacetyl (-) epicatechin 
• 1071725-97-7 3,7,3'-triacetyl (-) epicatechin 
• 548756-51-0 3,7,3',4'-tetraacetyl (-)-epicatechin 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 120786-78-9 (2R)-2r-(3,4-Dimethoxy-phenyl)-3c,5,7-trimethoxy-chroman 
• 874999-30-1 penta-O-acetyl-(-)-epicatechin-(4β,2)-tri-O-acetylphloroglucinol 
• 25121-65-7 (+/-)-3t-Acetoxy-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman 
• 26049-25-2 3,3',4',5,7-penta-O-methylcatechin 
• 51126-02-4 4β-bromopenta-O-acetyl-(-)-epicatechin 

Relevant articles and documents

Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities

Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5–9), and 17 known compounds (3, 4, and 10–24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual charact

Preparation method and application of hydroxyl cinnamyl ester type catechin

The invention relates to a preparation method and application of hydroxyl cinnamyl ester type catechins. The hydroxyl cinnamyl ester type catechins comprise four catechins which are respectively namedas epicatechin trans-coumarate, epicatechin trans-caffeic acid ester, epigallocatechin trans-coumarate and epigallocatechin trans-caffeic acid ester. The hydroxyl cinnamyl ester type catechins are prepared by the following steps: carrying out four steps of full acetylation on epicatechin and epigallocatechin, removal of acetyl on phenolic hydroxyl, silanizing of phenolic hydroxyl and removal of 3-acetyl, then respectively esterifying with acetylated caffeic acid or coumaric acid acyl chloride, and removing a protecting group. The preparation method of the four catechins is simple and mild inconditions, and can be completed under general experimental conditions. The four hydroxycinnamyl ester type catechins have a certain inhibition effect on the activity of alpha-glucosidase, can be usedfor hypoglycemic drugs, and have important significance in the fields of agriculture and medicine.

Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: Insight into the origin of the high regioselectivity of annulation

A synthesis method of doubly linked flavan dimers is reported via the acid-promoted annulation reaction using nascent catechins, (+)-catechin or (-)-epicatechin, as a dianionic partner and an ethylenedioxy-bridged flavan as a dicationic partner. Procyanidins A1 and A2 were synthesized. On the high regioselectivity of the annulation reactions, model experiments and computational studies were carried out.