18829-70-4

Usage

Uses

Used in Antioxidant Applications:
(-)-Catechin Hydrate is used as a natural antioxidant for its ability to neutralize free radicals and protect cells from oxidative damage. This property makes it a valuable ingredient in the pharmaceutical, cosmetic, and food industries.
Used in Dyeing and Tanning:
(-)-Catechin Hydrate is used as a dyeing and tanning agent due to its ability to bind with proteins and other macromolecules, making it suitable for the textile and leather industries.
Used in High-Performance Liquid Chromatography (HPLC):
(-)-Catechin Hydrate is used as a reference standard in HPLC for the quantification of polyphenols from plant extracts. This application is crucial for ensuring the accuracy and reliability of polyphenol measurements in various research and quality control settings.
Used in Kinetic Studies:
(-)-Catechin Hydrate is used as a reference standard in kinetic studies to quantify antioxidants from Iranian green tea leaves. This helps researchers understand the antioxidant capacity of green tea and its potential health benefits.
Used in Pharmaceutical Research:
(-)-Catechin Hydrate is used as a primary reference substance in pharmaceutical research, with assigned absolute purity considering chromatographic purity, water, residual solvents, and inorganic impurities. This ensures the accuracy and consistency of research results and product quality.
Used in the Food Industry:
(-)-Catechin Hydrate is used as an additive in the food industry for its antioxidant properties, which help extend the shelf life of products and maintain their freshness.
Used in the Cosmetic Industry:
(-)-Catechin Hydrate is used in the cosmetic industry for its antioxidant and anti-inflammatory properties, making it a valuable ingredient in skincare products aimed at reducing signs of aging and promoting skin health.

Biochem/physiol Actions

Catechins have wide biological functionality. They induce antiviral and anticancer activities. Catechins also play a key role in regulating carbohydrate and lipid metabolism. It prevents fat accumulation.

InChI:InChI=1/C15H14O6.H2O/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7;/h1-5,13,15-20H,6H2;1H2/t13-,15+;/m1./s1

Upstream product

• 114612-78-1 aesculitannin D 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 154-23-4 catechin 
• 108-73-6 3,5-dihydroxyphenol 
• 154-23-4 catechin 
• 154-23-4 (-)-catechin 
• 15963-96-9 leucocyanidin 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 
• 88038-00-0 6,8-dibromocatechin 
• 528-58-5 cyanidin chloride 
• 7295-85-4 catechin 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 

Downstream Products

• 104263-86-7 ent-catechin 3',4',5,7-tetra-O-methyl ether 
• 7295-85-4 catechin 
• 154-23-4 catechin 
• 88314-66-3 catechin-(4α->8)-ent-epicatechin 
• 16198-01-9 ((-)-catechol)-pentaacetate 
• 29441-79-0 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6,7-dione 
• 84282-42-8 catechin pentaacetate 
• 117820-40-3 8-iodocatechin pentaacetate 
• 117820-41-4 6-iodocatechin pentaacetate 
• 37972-41-1 o-Hydroxyphenylsaeure-α-methylsuccinat 
• 33491-08-6 Bernsteinsaeure-mono<2-hydroxy-phenylester> 
• 37972-42-2 o-Hydroxyphenylsaeure-α,α-dimethylsuccinat 
• 37972-44-4 o-Hydroxyphenylsaeurephthalat 
• 154-23-4 (-)-catechin 

Relevant academic research and scientific papers

11-β-hydroxysterols as possible endogenous stimulators of mitochondrial biogenesis as inferred from epicatechin molecular mimicry

Currently, there is great interest in identifying endogenous (i.e. physiological) stimulators of mitochondrial biogenesis (MB), in particular, those that may mediate the effects of exercise. The molecular size of the cacao flavanols (epicatechin and catechin) highly resembles that of sterols and epicatechin has been reported to activate cells surface receptors leading to the stimulation of MB in endothelial and skeletal muscle cells translating into enhanced exercise capacity. We therefore hypothesize, that epicatechin may be acting as a structural mimic of an as yet unknown sterol capable of stimulating MB. We developed a new synthetic process for obtaining enantiomerically pure preparations of (-)-epicatechin and (+)-epicatechin. Applying spatial analytics and molecular modeling, we found that the two isoforms of epicatechin, (-) and (+), have a structural resemblance to 11-β-hydroxypregnenolone, a sterol with no previously described biological activity. As reported in this proof-of-concept study performed in primary cultures of endothelial and muscle cells, 11-β-hydroxypregnenolone is one of the most potent inducers of MB as significant activity can be detected at femtomolar levels. The relative potency of (-)/(+)-epicatechin isoforms and on inducing MB correlates with their degree of spatial homology towards the 11-β-hydroxypregnenolone. On the basis of these results, the detailed in vivo characterization of the potential for these sterols to act as endogenous modulators of MB is warranted.

Effects of epigallocatechin gallate on the stability of epicatechin in a photolytic process

Catechins belonging to polyhydroxylated polyphenols are the primary compounds found in green tea. They are associated with many physiological properties. Epicatechin (EC) is a non-gallate-type catechin with four phenolic hydroxyl groups attached. The changes in EC treated with color light illumination in an alkaline condition were investigated by chromatographic and mass analyses in this study. In particular, the superoxide anion radical (O2??) was investigated during the EC photolytic process. EC is unstable under blue light illumination in an alkaline solution. When EC was treated with blue light illumination in an alkaline solution, O2?? was found to occur via a photosensitive redox reaction. In addition, the generation of monomeric, dimeric, and trimeric compounds is investigated. On the other hand, epigallocatechin gallate (EGCG), which is a gallate-type catechin, is stable under blue light illumination in an alkaline solution. Adding EGCG, during the blue light illumination treatment of EC decreased photolytic formation, suggesting that gallate-type catechins can suppress the photosensitive oxidation of EC. Gallate-type catechins are formed via the esterification of non-gallate-type catechins and gallic acid (GA). The carbonyl group on the gallate moiety of gallate-type catechins appears to exhibit its effect on the stability against the photosensitive oxidation caused by blue light illumination.

Metabolic characterization of the anthocyanidin reductase pathway involved in the biosynthesis of flavan-3-ols in elite Shuchazao tea (Camellia sinensis) cultivar in the field

Anthocyanidin reductase (ANR) is a key enzyme in the ANR biosynthetic pathway of flavan-3-ols and proanthocyanidins (PAs) in plants. Herein, we report characterization of the ANR pathway of flavan-3-ols in Shuchazao tea (Camellia sinesis), which is an elite and widely grown cultivar in China and is rich in flavan-3-ols providing with high nutritional value to human health. In our study, metabolic profiling was preformed to identify two conjugates and four aglycones of flavan-3-ols: (-)-epigallocatechin-gallate [(-)-EGCG], (-)-epicatechin-gallate [(-)-ECG], (-)-epigallocatechin [(-)-EGC], (-)-epicatechin [(-)-EC], (+)-catechin [(+)-Ca], and (+)-gallocatechin [(+)-GC], of which (-)-EGCG, (-)-ECG, (-)-EGC, and (-)-EC accounted for 70-85% of total flavan-3-ols in different tissues. Crude ANR enzyme was extracted from young leaves. Enzymatic assays showed that crude ANR extracts catalyzed cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively, in which (-)-EC and (-)-EGC were major products. Moreover, two ANR cDNAs were cloned from leaves, namely CssANRa and CssANRb. His-Tag fused recombinant CssANRa and CssANRb converted cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively. In addition, (+)-EC was observed from the catalysis of recombinant CssANRa and CssANRb. Further overexpression of the two genes in tobacco led to the formation of PAs in flowers and the reduction of anthocyanins. Taken together, these data indicate that the majority of leaf flavan-3-ols in Shuchazao's leaves were produced from the ANR pathway.

A catechin preparation method of compound (by machine translation)

The invention relates to a method for preparing a catechin compound. The method comprises the following steps: by taking 2,4,6-trihydroxy acetophenone and p-hydroxy benzaldehyde as raw materials, carrying out condensation reaction, restored deoxidation, cyclization reaction of acid catalysis, so as to obtain the catechin compound. The invention also provides a technology for producing the catechin compound. In the synthesis process of an immediate 9, reduction is carried out by using sodium borohydride which is catalyzed by a lewis acid, so that side reaction caused by double bond transfer is greatly reduced while a highly toxic reagent osmium tetroxide is replaced with hydrogen peroxide oxidation.

NOVEL APPROACH FOR SYNTHESIS OF CATECHINS

A process for synthesis of enatiomerically pure or enatiomerically enriched or racemic mixture of (+and/or?) epicatechin echm and its intermediates, comprising the steps of: (i) obtaining penta-protected quercetin; (ii) reducing the penta-protected quercetin obtained from step (i); (iii) optionally deprotecting the compound of step (ii); (iv) reducing the compound obtained from step (ii) or step (iii) in the presence of a chiral/achiral reducing agent to obtain a chiral intermediate; (v) deprotecting and/or hydrogenation of the chiral intermediate obtained from step (iv) to obtain (?)-epicatechin; (vi) optionally simultaneously deprotecting and by drogenation of the compound obtained from step (ii) to obtain racemic epicatechin.

NOVEL PROCESS FOR SYNTHESIS OF POLYPHENOLS

The present invention provides synthetic processes for preparing racemic and/or optically pure epicatechin, epigallocatechin and related polyphenols as such or as their variously functionalized derivatives. A principle objective of the disclosure is to provide a new and useful method of synthesis to obtain polyphenols in isomerically pure and/or racemic forms.

Photochemistry synthesis. Part 2: Enantiomerically pure polyhydroxy-1,1,3-triarylpropan-2-ols

A new method to open the heterocyclic ring of flavan-3-ols via photolytic cleavage of the ether bond, with stereoselective trapping of the intermediates with phloroglucinol to obtain phloroglucinol grafted derivatives of flavan-3-ols, was developed. Photolysis of catechin and epicatechin, respectively, in the presence of phloroglucinol yielded the enantiomeric (1S,2S)- and (1R,2R)-1,3-di(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl) propan-2-ols, respectively. The absolute configuration at C-1 and C-2 was determined by electronic circular dichroism (experimental and calculated) and these results confirmed that the trapping mechanism is controlled by the C-3 configuration of the flavan-3-ol.

A NOVEL PROCESS FOR SYNTHESIS OF POLYPHENOLS

The present invention provides synthetic processes for preparing racemic and/or optically pure epicatechin, epigallocatechin and related polyphenols as such or as their variously functionalized derivatives.

Epimerization of tea catechins under weakly acidic and alkaline conditions

Tea catechins in a buffer at pH 7 with N2 replacing O 2 epimerized rapidly at 80 °C with less than 10% of oxidative side reactions and gave catechin epimers in a 50-63% yield. The epimerization of catechins with three hydroxyl groups was faster than with two groups, and of galloyl-free catechins was faster than catechins with a galloyl ester.