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E4268

(−)-Epigallocatechin gallate

≥80% (HPLC), from green tea

Synonym(s):

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate, EGCG

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Pack SizeSKUAvailabilityPrice
100 mg
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$91.80

About This Item

Empirical Formula (Hill Notation):
C22H18O11
CAS Number:
989-51-5
Molecular Weight:
458.37
NACRES:
NA.79
PubChem Substance ID:
57654159
UNSPSC Code:
12352205
MDL number:
MFCD00075940

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biological source

green tea

Quality Level

200

assay

≥80% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

InChI key

WMBWREPUVVBILR-WIYYLYMNSA-N

Gene Information

human ... CYP1A2(1544)

General description

(−)-Epigallocatechin gallate, is a bioactive component of green tea accounting for 50-80% of the total catechin content.

Application

(−)-Epigallocatechin gallate has been used as:
  • a potential neuroprotective agent to test its protective effect against spinal cord injury and blood-spinal cord barrier (BSCB) leakage
  • an effective antioxidant against light-induced photoreceptor degeneration in mice retina[1]
  • an antioxidant in retinitis pigmentosa (RP) and reduces oxidative damage and changes circadian rhythms in pigmented heterozygous P23H rat[2]
  • to test its reversal effect on Diastolic dysfunction in restrictive cardiomyopathy (RCM) mice[3]
  • an anti-cancer agent in colorectal cancer in mice[4]

Biochem/physiol Actions

(−)-Epigallocatechin gallate (EGCG) comprises eight -hydroxyl (OH) groups that determine its high antioxidant property. Other than being an efficient free oxygen radical scavenger, it also acts as a good chelating agent and a modulator of important transcription factors, namely nuclear factor-kappa β (NF-kβ).[2] EGEC is proven to be an efficient anti-obesity agent by increasing energy expenditure, fat oxidation, and lowering appetite in humans.[5] EGCG also acts as an anti-inflammatory and neuroprotective agent in the initial stages of ischemia and spinal cord injury. It reduces caveolin-1 expression, maintaining blood-brain barrier integrity and downregulating pro-inflammatory cytokines.

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This Item
E4143324880PHL89656
(−)-Epigallocatechin gallate ≥80% (HPLC), from green tea

Sigma-Aldrich

E4268

(−)-Epigallocatechin gallate

(−)-Epigallocatechin gallate ≥95%

Sigma-Aldrich

E4143

(−)-Epigallocatechin gallate

(–)-Epigallocatechin Gallate One of the main polyphenolic constituents of green tea that exhibits potent antitumor, anti-inflammatory, and antioxidant properties.

Sigma-Aldrich

324880

(–)-Epigallocatechin Gallate

(−)-Epigallocatechin 3-gallate phyproof® Reference Substance

PHL89656

(−)-Epigallocatechin 3-gallate

biological source

green tea

biological source

-

biological source

-

biological source

-

assay

≥80% (HPLC)

assay

≥95%

assay

≥95% (HPLC)

assay

≥95.0% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Gene Information

-

Gene Information

-

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7896V
WXBF5873V
WXBF2464V
WXBF0250V
SLCM8972

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Articles

Dietary Antioxidants

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.

Related Content

Tea polyphenols-their antioxidant properties and biological activity-a review
Gramza A, et al.,
Polish Journal of Food and Nutrition Sciences, 14(3), 219-219 (2005)
Tia M Rains et al.
The Journal of nutritional biochemistry, 22(1), 1-7 (2010-12-01)
Green tea catechins (GTC) are polyphenolic compounds present in the unfermented dried leaves of the plant, Camellia sinensis. Results from a number of randomized, controlled intervention trials have shown that consumption of GTC (270 mg to 1200 mg/day) may reduce
Shounan Qi et al.
Molecular vision, 23, 171-178 (2017-05-02)
(-)-epigallocatechin-3-gallate (EGCG), a major catechin component of green tea, is reported to delay or prevent certain forms of cancer, arthritis, cardiovascular disease, and neurodegenerative disorders. In this study, we determined if systemically administered EGCG could protect the retina against light
View All Related Papers

Global Trade Item Number

SKUGTIN
E4268-100MG04061833603581

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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