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Merck

E3768

(−)-Epigallocatechin

≥95% (HPLC), from green tea

Synonyme(s) :

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane

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5 MG

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A propos de cet article

Formule empirique (notation de Hill) :
C15H14O7
Numéro CAS:
Poids moléculaire :
306.27
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:

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Nom du produit

(−)-Epigallocatechin, ≥95% (HPLC), from green tea

InChI key

XMOCLSLCDHWDHP-IUODEOHRSA-N

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3

InChI

1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

biological source

green tea

assay

≥95% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

Gene Information

human ... CYP1A2(1544)

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Cet article
E4268E3893E4143
biological source

green tea

biological source

green tea

biological source

green tea

biological source

-

assay

≥95% (HPLC)

assay

≥80% (HPLC)

assay

≥98% (HPLC)

assay

≥95%

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Application

(−)-Epigallocatechin (EGC) has been used:
  • as a reference standard in high-performance liquid chromatography (HPLC) analysis[1]
  • to analyze its inhibitory effect on α-amylase and α-glucosidase activity to control postprandial hyperglycemia in Diabetes mellitus[2]
  • in cell viability assays to check its efficacy and protection against ferroptosis and iron toxicity in murine pancreatic β-cells[3]
  • to evaluate its potential anti-inflammatory effects on long-term acute and chronic Pristen-induced arthritis[4]
  • to treat pregnant and nursing mice, on in vitro angiogenesis, proliferation, and movement of endothelial cells[5]
  • to evaluate its effect on pregnant and nursing mice spleen based on the number and localization of CD4+ (cluster of differentiation 4) and CD8+ cluster of differentiation 8) cells[6]

Biochem/physiol Actions

(−)-Epigallocatechin (EGC) has proven to be an anti-cancer agent by its inhibitory effects on heregulin-b1 (HRG)-induced migration/invasion in MCF-7 human breast carcinoma cells.[7] It has also shown strong antiviral activity against the herpes simplex virus.[8]
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.

General description

(−)-Epigallocatechin is one of the main catechin compounds found in green tea and the most abundant one (~20%), with antioxidant properties.[9][10]

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

Yukihiro Kushima et al.
Biological & pharmaceutical bulletin, 32(5), 899-904 (2009-05-08)
Migration/invasion is involved in the multiple steps of metastasis, resulting in a poor prognosis of breast cancer. (-)-Epigallocatechin-3-gallate (EGCG) in green tea inhibits the metastasis of some cancer cell lines. Cell migration/invasion assays using Boyden chambers demonstrated that (-)-epigallocatechin (EGC)
Sławomir Lewicki et al.
Central-European journal of immunology, 42(1), 10-16 (2017-07-07)
Rhodiola kirilowii, a member of Crassulaceae family, grows wildly in Asiatic mountains and is also cultivated in some European countries. Its underground parts traditionally are used for enhance physical and mental performance of the body. In our previous papers we
Evaluation of alpha-amylase and alpha-glucosidase inhibitory activity of flavonoids
Gu C, et al.,
International Journal of Food and Nutrition Science, 2(6), 1-6 (2015)
Anna Leichsenring et al.
PloS one, 11(3), e0152518-e0152518 (2016-03-31)
Rheumatoid arthritis (RA)--a widespread chronic inflammatory disease in industrialized countries--is characterized by a persistent and progressive joint destruction. The chronic pro-inflammatory state results from a mutual activation of the innate and the adaptive immune system, while the exact pathogenesis mechanism
Robert Zdanowski et al.
Central-European journal of immunology, 42(1), 17-23 (2017-07-07)
Angiogenesis plays an important role in many physiological processes, among them the formation of tissues and organs during embryogenesis. A lot of medicinal plants exhibit angiomodulatory properties. This creates the need for a thorough check of whether the plant extracts

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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