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C1251

Sigma-Aldrich

(+)-Catechin hydrate

≥98% (HPLC), powder

Synonym(s):

(+)-Cyanidol-3, (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol

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About This Item

Empirical Formula (Hill Notation):
C15H14O6 · xH2O
CAS Number:
225937-10-0
Molecular Weight:
290.27 (anhydrous basis)
Beilstein:
3595244
EC Number:
205-825-1
MDL number:
MFCD00150865
UNSPSC Code:
12352200
PubChem Substance ID:
57653982
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

yellow to yellow with tan cast

mp

175-177 °C (anhydrous) (lit.)

solubility

ethanol: 50 mg/mL

storage temp.

2-8°C

SMILES string

[H]O[H].O[C@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3

InChI

1S/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+;/m0./s1

InChI key

OFUMQWOJBVNKLR-NQQJLSKUSA-N

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General description

Catechins are phytochemicals, richly present in black grapes, peaches, strawberries and broad beans. Catechins occur in various forms such as catechins, epicatechin, epicatechin gallate, epigallocatechin and epigallocatechin gallate.

Application

(+)-Catechin hydrate has been used:
  • as a polyphenol standard in the determination of total polyphenols in the by-products of red wine
  • as an additive to study its effects on in vitro methane production and substrate degradation in a triple-fed batch approach
  • as a substrate to determine the activity of pure L. plantarum CECT 748T 14 recombinant tannase on catechin

Biochem/physiol Actions

An antioxidant flavonoid of plant origin; a free radical scavenger, preventing free radical-mediated damage in a variety of biological systems. For example, at physiological pH catechin suppressed DNA strand breaks by hydroxyl radicals. It has also been shown to prevent human plasma oxidation. It delayed the consumption of endogenous lipid-soluble antioxidants and inhibited lipid oxidation. Catechin may also function as an inhibitor of fatty acid synthase.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S B Lotito et al.
Free radical biology & medicine, 24(3), 435-441 (1998-01-23)
Based on the recognized capacity of (+)-catechin (CTCH) to prevent free radical-mediated damage in different biological systems, its role in the protection of human plasma from oxidation was investigated. Samples of human blood plasma were incubated with 50 mM AAPH
Christine Ziegler et al.
Molecular microbiology, 78(1), 13-34 (2010-10-07)
Increases in the environmental osmolarity are key determinants for the growth of microorganisms. To ensure a physiologically acceptable level of cellular hydration and turgor at high osmolarity, many bacteria accumulate compatible solutes. Osmotically controlled uptake systems allow the scavenging of
Nutrition and Health Info Sheet: Catechins (2008)
J Ueda et al.
Archives of biochemistry and biophysics, 333(2), 377-384 (1996-09-15)
The reactivities of various antioxidative compounds including catechol derivatives and endogenous radical scavengers toward hydroxyl radical (.OH) were investigated by an electron spin resonance-spin trapping method, thiobarbituric acid method, and DNA strand scission assay. Hydroxyl radical was generated by both
Hadeer M Ezzat et al.
International journal of pharmaceutics, 565, 488-498 (2019-05-18)
Catechin hydrate is a phytopharmaceutical with promising anticancer effects but poor bioavailability. This study aimed to elaborate catechin loaded chitosan-tethered liposomes (chitosomes) to enhance catechin oral bioavailability. Nanocarriers were optimized via ethanol injection method followed by physicochemical, ex vivo and
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