Uses
ChemicalBook > CAS DataBase List > (-)-Epigallocatechin gallate

(-)-Epigallocatechin gallate

Uses
Product Name
(-)-Epigallocatechin gallate
CAS No.
989-51-5
Chemical Name
(-)-Epigallocatechin gallate
Synonyms
EGCG;EPIGALLOCATECHIN GALLATE;ECGC;(-)-Epigallocatechin-3-O-gallate (20 mg);epigallocatechin3-gallate;Epigallocatechin-3-Monogallate;(-)-epigallocatechin 3-gallate;E-5187;(EGCE);EGCG-d6
CBNumber
CB2227188
Molecular Formula
C22H18O11
Formula Weight
458.37
MOL File
989-51-5.mol
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(-)-Epigallocatechin gallate Property

Melting point:
222-224°C
alpha 
D -185 ±2°(ethanol)
refractive index 
-175.5 ° (C=1, EtOH)
storage temp. 
2-8°C
solubility 
H2O: ≥5mg/mL, clear
form 
Solid
Boiling point:
909.1±65.0 °C(Predicted)
Density 
1.90±0.1 g/cm3(Predicted)
pka
7.75±0.25(Predicted)
color 
White to Light Brown
Water Solubility 
Soluble in ethanol, dimethyl formamide, water.
Merck 
14,3526
Stability:
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
InChIKey
WMBWREPUVVBILR-WIYYLYMNSA-N
LogP
0.639 (est)
CAS DataBase Reference
989-51-5(CAS DataBase Reference)
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Safety

Safety Statements 
24/25
WGK Germany 
2
RTECS 
KB5200000
F 
10-23
HS Code 
29339900
Toxicity
LD50 oral in mouse: 2170mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHL89656
Product name
(−)-Epigallocatechin3-gallate
Purity
phyproof?ReferenceSubstance
Packaging
50mg
Price
$382
Updated
2024/03/01
Sigma-Aldrich
Product number
1236700
Product name
(?)-Epigallocatechin gallate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
20mg
Price
$394
Updated
2024/03/01
Sigma-Aldrich
Product number
03970590
Product name
Epigallocatechin gallate
Purity
primary pharmaceutical reference standard
Packaging
10mg
Price
$364
Updated
2024/03/01
TCI Chemical
Product number
E0694
Product name
(-)-Epigallocatechin Gallate Hydrate
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$99
Updated
2024/03/01
TCI Chemical
Product number
E0694
Product name
(-)-Epigallocatechin Gallate Hydrate
Purity
>98.0%(HPLC)
Packaging
500mg
Price
$273
Updated
2024/03/01
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(-)-Epigallocatechin gallate Chemical Properties,Usage,Production

Uses

(-)-Epigallocatechin Gallate is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-ß and amaloid plaques in mice. This compound has neuroprotective properties.

Chemical Properties

solid

Uses

telomerase inhibitor

Uses

An inhibitor of Bcl-2 and NOS2

Uses

(-)-Epigallocatechin Gallate is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-β and amaloid plaques in mice. This compound has neuroprotective properties.

Uses

A tumor-inhibiting constituent of green tea. Alters the cleavage of amyloid precursor protein, decreasing production of amaloid- and amaloid plaques in mice

Definition

ChEBI: (-)-epigallocatechin 3-gallate is a gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. It has a role as an antineoplastic agent, an antioxidant, a Hsp90 inhibitor, a neuroprotective agent, a plant metabolite, a geroprotector and an apoptosis inducer. It is a gallate ester, a polyphenol and a member of flavans. It is functionally related to a (-)-epigallocatechin.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Epigallocatechin gallate is a potent polyphenolic flavonoid which is found as a component of tea. It exhibits antioxidant, antimutagenic, antitumor and anti-inflammatory properties, thereby contributing to the health-beneficial actions. It finds potential use as a drug candidate in the pharmaceutical, cosmetic, and nutritional fields.

Hazard

Moderately toxic by ingestion.

Biological Activity

(-)-epigallocatechin gallate (egcg), the major catechin accounting for 59% of the total catechins in green tea, is a powerful antioxidant as well as an antiangiogenic and antitumor agent. egcg has been studied for its role in the chemoprevention of a wild range of cancers, including liver, stomach, skin, lung, mammary gland and colon cancers. study results show that egcg is able to induce apoptosis, promote cell growth arrest and block carcinogenesis by affecting signal transduction pathways. moreover, egcg exhibits inhibition against a variety of viruses, including hcv, hiv-1, hbv, hsv-1, hsv-2, ebv, adenovirus, influenza virus and enterovirus, as well as several enzymes, including dnmts, proteases and dhfr.singh bn, shankar s, srivastava rk. green tea catechin, epigallocatechin-3-gallate (egcg): mechanisms, perspectives and clinical applications. biochem pharmacol. 2011; 82(12):1807-1821.steinmann j, buer j, pietschmann t, steinmann e. anti-infective properties of epigallocatechin-3-gallate (egcg), a component of green tea. br j pharmacol. 2013; 168(5):1059-1073

Biochem/physiol Actions

(-)-Epigallocatechin gallate (EGCG), an antioxidant polyphenol flavonoid exerts anti-tumor properties by inhibiting telomerase and DNA methyltransferase activity. EGCG inhibits the expression of matrix metalloproteinase-2 (MMP-2), MMP-9 and reduces the invasiveness. EGCG blocks the activation of epidermal growth factor (EGF) receptors and human epidermal growth factor receptor-2 (HER-2). EGCG increases bone mineral density and reduces bone resorption. EGCG inhibits osteoclastogenesis by inhibiting receptor activator of nuclear factor κ-B ligand (RANKL) induced nuclear factor κ B (NF-κB) transcriptional activity. EGCG reduces skeletal muscle atrophy. EGCG has anti-aging property and increases myogenic differentiation. EGCG inhibits fatty acid synthase and glutamate dehydrogenase activity.

Anticancer Research

EGCG and EGC are the active polyphenol compounds found in green tea, found toinhibit p-glycoprotein transport activities in Chinese hamster ovary (p-gp+) cells.EGCG facilitates the retraction of MDR phenotype by reducing cellular drug effluxwhen given in combination with vinblastine or doxorubicin. Hesperetin, quercetin,daidzein, silymarin, naringenin, and resveratrol also inhibit the MRP1, MRP4, andMRP5 (Kawasaki et al. 2008). Curcumin increases the cellular accumulation ofanticancer agents like cisplatin, tamoxifen, daunorubicin, vincristine, anddoxorubicin and thereby effectively sensitizes the drug-resistant cancer cells. Areduction in MDR1B expression in L1210/Adr cells (mouse leukemic MDR cells)by curcumin is mediated by PI3K, Akt, and NF-κB pathways. It also inhibits theABCG2 transporter activity. In addition curcumin facilitates the accumulation ofmitoxantrone and doxorubicin in ABCG2-expressing HEK cells and hence reversesMDR (Kawasaki et al. 2008; Dandawate et al. 2013).

Anticancer Research

EGCG is an ester of gallic acid and epigallocatechin and is a catechin compound(Murakami et al. 1996). It is found most abundantly in green tea. It can be used to treat brain, prostate, cervical, and bladder cancers (Wang et al. 2012). It suppressesthe ornithine decarboxylase action, an enzyme that leads to rapid proliferation andfurthermore circumvents apoptosis (Singh et al. 2016a). It suppresses nuclear factor(NF-κB) activation and expression of Bcl-2 (B-cell lymphoma 2) as well as COX-2(cyclooxygenase-2) in prostate cancer cells and causes induction of apoptosis. Ithamper the matrix metallopeptidase-9 (MMP-9) activation in bladder and lungcancer cells and suppresses the synthesis of VGEF (vascular endothelial growthfactor) in head and neck cancers. It prevents ERK (extracellular signal-regulatedkinase) phosphorylation and MMP-2 and MMP-9 activation and suppresses ERK,c-Jun N-terminal kinase (JNK), and MMP-9 expressions in gastric carcinoma cells(Singh et al. 2016a). It is binding and inhibits the antiapoptotic protein Bcl-xL,interferes with EGFR (epidermal growth factor receptor) signaling, and inhibitshepatocyte growth factor-induced cell proliferation and MAPK (mitogen-activatedprotein kinase), CDK (cyclin-dependent kinase), and cell signaling linked to growthfactors (Wang et al. 2012; Du et al. 2012).
Green tea constitutes the rich amount of EGCG which aids in cancer chemoprevention(Fujiki et al. 1998). EGCG improved the impacts of ginseng compoundin the restraint of colon tumor cell development, showing that green tea could bea successful synergist with an anticancer agent for malignancy chemoprevention.It obstructs the PDGF-initiated proliferation and migration of rodent pancreaticstellate cells (Masamune et al. 2005). The soluble and plasma membrane-integratedEGCG straightforwardly communicates with PDGF-BB and in this wayputs off precise receptor binding promoting the inhibitory impacts of EGCG onplatelet-derivedgrowth factor-incited cell signaling and mitogens (Weber et al.2004).

storage

Store at -20°C

(-)-Epigallocatechin gallate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (-)-Epigallocatechin gallate manufacturers

Changsha Staherb Natural Ingredients Co., Ltd.
Product
Green Tea Extract; (-)-Epigallocatechin gallate EGCG 989-51-5
Price
US $0.00/kg
Min. Order
1kg
Purity
98% HPLC
Supply Ability
1000KG
Release date
2022-09-27
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Epigallocatechin Gallate/ EGCG Powder 989-51-5
Price
US $180.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-23
Baoji Guokang Bio-Technology Co., Ltd.
Product
(-)-Epigallocatechin gallate 989-51-5
Price
US $400.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1-1000kg
Release date
2021-06-07

989-51-5, (-)-Epigallocatechin gallateRelated Search:

L-Epicatechin Propyl gallate Pyrogallol Gallic acid monohydrate Methyl gallate Dihydromyrcenol Gallic acid (-)-Gallocatechin gallate Crospovidone (-)-Epigallocatechin (-)-EGCG-3'-O-ME (-)-EGCG-4'-O-ME (-)-EGCG-3''-O-ME (-)-EPIGALLOCATECHIN 3-(4''-O-METHYL)GALLATE (-)-Epigallocatechin gallate OCTANICOTINOYL EPIGALLOCATECHIN GALLATE,OCTANICOTINOYL EPIGALLOCATECHIN GALLATE Epigallocatechin gallate solution,Epigallocatechin gallate solution GREEN TEA EXTRACT/ POLYPHENOL/ EPIGALLOCATECHIN GALLATE,GREEN TEA EXTRACT/ POLYPHENOL/ EPIGALLOCATECHIN GALLATE

  • TEA CATECHIN
  • (-)-Epigallocatechin-3-O-gallate (20 mg)
  • EGCG, (-)-Epigallocatechin gallate/Green Tea EGCG90
  • EGCG, (-)-Epigallocatechin gallate/Green Tea Extract
  • (-)-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
  • Epigallocatechin-3-Monogallate
  • L-Epigallocatechin Gallate
  • (-)-Epigallocatechin Gallate-d6
  • 3-O-Galloyl-(-)-epigallocatechin-d6
  • EGCG-d6
  • epi-Gallocatechin 3-O-Gallate-d6
  • epi-Gallocatechin Gallate-d6
  • Epigallocatechin-3-Monogallate-d6
  • L-Epigallocatechin Gallate-d6
  • (-)-cis-3,4-Dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2H)-benzopyran-3-yl Gallate EGCG
  • Teatannin II
  • EGCG, (-)-Epigallocatechin gallate/Green Tea EGCG95
  • 3-(3,4,5-TRIHYDROXYBENZOATE)
  • Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
  • cis-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoatehydrate
  • (-)-epigallocatechin-3-o-gallate
  • (-)-epigallocatecholgallate
  • 3-gallate,(-)-epigallocatecho
  • epigallocatechin3-gallate
  • Epigallocathecinfromgreentea
  • EGCG (epigallocatechin gallate)
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 50% BY HPLC
  • TEAVIGO(TM)
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 95% BY HPLC
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 30% BY HPLC
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 98% BY HPLC
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 70% BY HPLC
  • EPIGALLOCATECHIN GALLATE, (EGCG) FROM GREEN TEA 90% BY HPLC
  • EGCG: E-5187(-)-EPIGALLOCATECHIN GALLATE
  • Egcg90%
  • EpigallocatechinGallate(Egcg)
  • (-)-cis-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2h)-benzopyran-3-yl gallate
  • (-)-epigallocatechin gallate from green tea
  • EPIGALLOCATCCHINGALLATE
  • [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
  • EPIGALLOCATECHIN GALLATE, (-)- SNAPN 0.1mg/mL(SH)
  • EPIGALLOCATECHIN GALLATE, (-)-(P)
  • EPIGALLOCATECHIN GALLATE, (-)-(SH)
  • (-)-EPIGALLOCATECHIN GALLATE hplc
  • (-)EPIGALLOCATECHIN GALLATE WITH HPLC
  • Green tea extract/EGCG
  • Benzoicacid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-
  • dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-ylester,(2R-cis)-
  • EGCG, (-)-cis-3,3μ,4μ,5,5μ,7-Hexahydroxy-flavane-3-gallate, (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate
  • (-)-Epigallocatechin gallate ,98%
  • 3,4,5-Trihydroxybenzoic acid [(2R,3R)-3,4-dihydro-5,7-dihydroxy-2α-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3α-yl] ester
  • (-)-Epigallocatehin gallate
  • EGCG(Green Tea Extract)
  • [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
  • 3,4,5-trihydroxybenzoic acid [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] ester
  • epigallocathequin gallate
  • ()-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(
  • ()-Epigallocatechin gallate,()-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