35323-91-2

Usage

Uses

Used in Pharmaceutical Industry:
(-)-EPICATECHIN is used as an antioxidant agent for its ability to neutralize harmful free radicals and protect cells from oxidative damage. This property makes it a valuable component in the development of drugs aimed at treating various diseases associated with oxidative stress.
Used in Oncology:
(-)-EPICATECHIN is used as an antineoplastic agent for its cancer-inhibiting properties. It has been shown to interfere with the growth and proliferation of cancer cells, making it a potential candidate for the development of novel cancer treatments.
Used in Nutraceutical Industry:
(-)-EPICATECHIN is used as a dietary supplement for its health-promoting benefits. Its antioxidant and antineoplastic properties contribute to overall well-being and may help reduce the risk of developing certain diseases, including cancer.
Used in Cosmetic Industry:
(-)-EPICATECHIN is used as an ingredient in skincare products for its antioxidant properties. It can help protect the skin from environmental damage, reduce the appearance of fine lines and wrinkles, and promote a more youthful and radiant complexion.
Used in Food and Beverage Industry:
(-)-EPICATECHIN is used as a natural additive in the food and beverage industry for its antioxidant properties. It can help extend the shelf life of products, enhance their nutritional value, and provide health benefits to consumers.

InChI:InChI=1/C15H14O6/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/t13-,15-/m0/s1

Upstream product

• 154-23-4 catechin 
• 20315-25-7 procyanidin B₁ 
• 7732-18-5 water 
• 212265-19-5 2,4,6-tris(O-methoxymethyl)benzaldehyde 
• 528-58-5 cyanidin chloride 
• 13306-05-3 cyanidin 
• 7295-85-4 catechin 
• 154-23-4 (-)-catechin 
• 15963-96-9 leucocyanidin 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 67052-53-3 4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 732298-15-6 (+)-(2S,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol 
• 29106-49-8 procyanidin B₂ 
• 12798-57-1 procyanidin B₅ 
• 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 
• 104079-72-3 6-iodocatechin 
• 117820-39-0 8-iodocatechin 
• 117820-42-5 6,8-diiodocatechin 
• 33491-08-6 Bernsteinsaeure-mono<2-hydroxy-phenylester> 

Relevant academic research and scientific papers

Screening for the active anti-inflammatory and antioxidant polyphenols of gaultheria procumbens and their application for standardisation: From identification through cellular studies to quantitative determination

Aerial parts, leaves, and stems of Gaultheria procumbens are polyphenol-rich herbal medicines with anti-inflammatory and antioxidant effects. The present study focused on identifying active markers of the G. procumbens extracts in an integrated approach combining phytochemical and biological capacity tests. The target compounds, representing all classes of Gaultheria polyphenols, were pre-selected by LC-ESI-PDA-MS/MS. For unambiguous identification, the key analytes, including a rare procyanidin trimer (cinnamtannin B-1), miquelianin potassium salt, and two new natural products: quercetin and kaempferol 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosides, were isolated by preparative HPLC and investigated by spectroscopy (HR-ESI-MS, UV-vis, CD, 1D-and 2D-NMR), thiolysis, flame photometry, optical rotation experiments, and absolute configuration studies. The significant contribution of the pre-selected compounds to the biological effects of the extracts was confirmed in vitro: the analytes significantly and in a dose-dependent manner down-regulated the pro-oxidant and pro-inflammatory functions of human neutrophils ex vivo (inhibited the release of reactive oxygen species, IL-1β, TNF-α, and neutrophils elastase, ELA-2), inhibited two key pro-inflammatory enzymes (cyclooxygenase, COX-2, and hyaluronidase), and most of them, except gaultherin, exerted potent direct antioxidant activity (ferric reducing antioxidant power and superoxide anion scavenging capacity). Moreover, cellular safety was confirmed for all compounds by flow cytometry. Eventually, as these mechanisms have been connected to the health benefits of G. procumbens, 11 polyphenols were accepted as active markers, and a simple, accurate, reproducible, and fully validated RP-HPLC-PDA method for standardisation of the target extracts was proposed.

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.

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC

A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.

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.

Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin

Thermal transformation of the (+)-catechin (1) with heating processing afforded a new oxidation product, gambiriin D (2), along with catechin [6′-8]-catechin (3), and (+)-epicatechin (4). The structure of a new catechin dimer with C-C linkage was determined on the basis of spectroscopic data interpretation. The catechin dimers 2 and 3 exhibited significantly improved inhibitory activities against α-glucosidase, with IC50 values of 0.16 ± 0.2 and 0.14 ± 0.2 μM, respectively, when compared to parent (+)-catechin. Kinetic analysis showed that the two effective compounds 2 and 3 have noncompetitive modes of action.

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.

The epimerase activity of anthocyanidin reductase from Vitis vinifera and its regiospecific hydride transfers

Anthocyanidin reductase (ANR) from Vitis vinifera catalyzes an NADPH-dependent double reduction of anthocyanidins producing a mixture of (2S,3R)- and (2S,3S)-flavan-3-ols. At pH 7.5 and 30°C, the first hydride transfer to anthocyanidin is irreversible, and no intermediate is released during catalysis. ANR reverse activity was assessed in the presence of excess NADPq. Analysis of products by reverse phase and chiral phase HPLC demonstrates that ANR acts as a flavan-3-ol C3-epimerase under such conditions, but this is only observed with 2R-flavan-3-ols, not with 2S-flavan-3-ols produced by the enzyme in the forward reaction. In the presence of deuterated coenzyme 4S-NADPD, ANR transforms anthocyanidins into dideuterated flavan-3-ols. The regiospecificity of deuterium incorporation into catechin and afzelechin - derived from cyanidin and pelargonidin, respectively - was analyzed by liquid chromatography coupled with electrospray ionization-tandem mass spectrometry (LC/ESI-MS/MS), and it was found that deuterium was always incorporated at C2 and C4. We conclude that 3-epimerization should be achieved by tautomerization between the two hydride transfers and that this produces a quinone methide intermediate which serves as C4 target of the second hydride transfer, thereby avoiding any stereospecific modification of carbon 3. The inversion of C2 stereochemistry required for reverse epimerization suggests that the 2S configuration induces an irreversible product dissociation.