18829-70-4

Basic information

• Product Name: (-)-CATECHIN HYDRATE
• Synonyms: (+)-TRANS-3,3',4',5,7-PENTAHYDROXYFLAVANE;(-)-CATECHIN HYDRATE;(L)-CATECHIN HYDRATE;3,5,7,3',4'-PENTAHYDROXYFLAVANE HYDRATE;(2S,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL;(2S-trans)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol;(2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-pyran-3,5,7-triol, 3,3,4,5,7-Pentahydroxyflavan, (-)-Cyanidanol-3;(2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, (-)-trans-3,3μ,4μ,5,7-Pentahydroxyflavane
• CAS NO: 18829-70-4
• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 308.28
• EINECS: 242-611-7
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 18829-70-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 93-96°; 175-177° when anhydr
• Boiling Point: 630.4 °C at 760 mmHg
• Flash Point: 335 °C
• Appearance: /
• Density: 1.593 g/cm³
• Vapor Pressure: 1.09E-20mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 9.54±0.10(Predicted)
• CAS DataBase Reference: (-)-CATECHIN HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-CATECHIN HYDRATE(18829-70-4)
• EPA Substance Registry System: (-)-CATECHIN HYDRATE(18829-70-4)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 18829-70-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 18829-70-4 differently. You can refer to the following data:
1. A natural phenol antioxidant plant secondary metabolite.
2. In dyeing and tanning.
3. (-)-Catechin has been used: to test its binding affinity towards estrogen receptor as a reference standard in high-performance liquid chromatography for quantification of polyphenols from plant extracts (HPLC)as a reference standard in kinetic studies to quantify antioxidants from Iranian green tea leaves

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

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

• 130405-40-2 (-)-catechin gallate 
• 7732-18-5 water 
• 154-23-4 catechin 
• 13306-05-3 cyanidin 
• 15963-96-9 leucocyanidin 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 
• 528-58-5 cyanidin chloride 
• 7295-85-4 catechin 
• 154-23-4 catechin 
• 1392190-80-5 pentabenzylated cyanidin 
• 13157-90-9 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one 
• 1392108-91-6 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran 
• 1392108-90-5 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)-4H-1-benzopyran 
• 117-39-5 quercetol 

Downstream Products

• 104263-86-7 ent-catechin 3',4',5,7-tetra-O-methyl ether 
• 7295-85-4 catechin 
• 154-23-4 catechin 
• 16198-01-9 (+/-)-epicatechol pentaacetate 
• 104079-72-3 6-iodocatechin 
• 117820-39-0 8-iodocatechin 
• 117820-42-5 6,8-diiodocatechin 
• 88314-66-3 catechin-(4α->8)-ent-epicatechin 
• 47299-80-9 (+/-)-5,7-O-dimethylepicatechin 
• 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 
• 108-73-6 3,5-dihydroxyphenol 

Relevant articles and documents

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.

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.

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.