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Home > Encyclopedia > Epigallocatechin gallate

Epigallocatechin gallate

pharmaceutical raw materials
Epigallocatechin gallate structure

Epigallocatechin gallate 

structure
  • CAS No:

    989-51-5

  • Formula:

    C22H18O11

  • Chemical Name:

    Epigallocatechin gallate

  • Synonyms:

    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;Epigallocatechol,3-gallate,(-)-;Benzoic acid,3,4,5-trihydroxy-,3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester,(2R-cis)-;Epigallocatechol,3-gallate;Epigallocatechol,gallate;Gallic acid,3-ester with epigallocatechol,(-)-;(-)-Epigallocatechin gallate;(-)-Epigallocatechol gallate;(-)-Epigallocatechin 3-gallate;Epigallocatechin gallate;Epigallocatechin 3-gallate;3-O-Galloyl-(-)-epigallocatechin;(-)-Epigallocatechin 3-O-gallate;L-Epigallocatechin gallate;epi-Gallocatechin 3-O-gallate;(-)-epi-Gallocatechin 3-O-gallate;NVP-XAA 723;Epigallocatechin 3-O-gallate;Epigallocatechin-3-monogallate;Teavigo;PF-EGCg 90;EGCG;epi-Gallocatechin gallate;Theliokeep;Teafuran 90S;EGCg-OP;863-65-0;435276-52-1

  • Categories:

    Cosmetic Ingredient  >  Antioxidant Ingredient

Description

solid


Solid


(-)-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 derives from a (-)-epigallocatechin.|Epigallocatechin gallate has been investigated for the treatment of Hypertension and Diabetic Nephropathy.|Hydroxycut is the commercial name a variety of multi-ingredient nutritional supplements (MINS) marketed for weight loss, body building and “fat burning”. In 2004, Hydroxycut products containing ephedra were withdrawn from use in the United States because of cardiovascular risks and in 2009 because of hepatotoxicity. Nevertheless, Hydroxycut products with different ingredients are still commercially available and have continued to be implicated in cases of clinically apparent acute liver injury.|SLIMQUICK is a popular, proprietary line of multi-ingredient nutritional supplements (MINS) marketed as weight loss products and sold widely in pharmacies and grocery stores as well on the internet. The major ingredients in the products include green tea extract, caffeine and various herbal, fruit and vegetable extracts. There have been rare reports of clinically apparent liver injury in patients taking SLIMQUICK products, the majority of which had clinical features suggestive of green tea hepatotoxicity.|Epigallocatechin Gallate is a phenolic antioxidant found in a number of plants such as green and black tea. It inhibits cellular oxidation and prevents free radical damage to cells. It is under study as a potential cancer chemopreventive agent. (NCI)

Epigallocatechin gallate Basic Attributes

458.37

458.37

479-560-7

BQM438CTEL

DTXSID1029889|DTXSID6020567|DTXSID0031398

C1088

29339900

Characteristics

197

1.2

Solid

1.90±0.1 g/cm3(Predicted)

217 °C

909.1°C at 760 mmHg

320ºC

1.857

soluble in ethanol, dimethyl formamide, water.H2O: ≥5mg/mL, clear

2-8°C

LD50 oral in mouse: 2170mg/kg

D -185 ±2°(ethanol)

206.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

2

24/25

KB5200000

Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, P501

H302

|Warning|H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 7 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hydroxycut has been associated with at least 50 instances of clinically apparent acute liver injury, but the specific Hydroxycut product implicated in different cases has varied and the specific ingredients responsible for liver injury remain unclear. In reported cases, the onset of injury was generally within 2 to 12 weeks of starting regular use. The typical presenting symptoms were fatigue, nausea, and abdominal pain followed by dark urine and jaundice. The pattern of liver injury was hepatocellular with serum aminotransferase levels as high as several thousand U/L, while alkaline phosphatase levels tended to be normal or minimally elevated (less than 3 times ULN). Liver biopsies showed an acute hepatitis-like picture, and severe cases were associated with confluent, submassive or massive necrosis. Immunoallergic and features were not common although autoantibodies were detected in a proportion of cases. The mortality rate overall was approximately 10% among cases with jaundice. In nonfatal cases, symptoms resolved within 1 to 8 weeks and laboratory tests return to normal within two to three months. The phenotype associated with Hydroxycut products was clearly an acute, self-limited viral hepatitis-like syndrome. Nevertheless, rare instances of cholestatic or mixed hepatitis with prolonged jaundice have also been reported in patients taking Hydroxycut products.|The initial reports of liver injury attributed to SLIMQUICK were published in 2012, with subsequent reports in 2014 and 2016, all from the United States. At least two dozen cases attributed to SLIMQUICK products have been described in the literature. These publications described an acute hepatocellular injury arising within 3 to 12 weeks of starting a SLIMQUICK product that contained green tea extract and caffeine along with several botanical extracts, the concentrations of which were not provided. The injury was moderate in severity and resolved within 1 to 2 months of stopping the dietary supplement (Case 1). At least one case resulted in need for emergency liver transplantation. Immunoallergic features were not present, but several patients had autoantibodies. Liver histology suggested drug induced liver injury rather than autoimmune hepatitis. The injury resolved once the nutritional supplement was stopped, but in some cases corticosteroids were used. Chronic or recurrent injury without reexposure did not occur.

Drug Information

Hydroxycut is the commercial name a variety of multi-ingredient nutritional supplements (MINS) marketed for weight loss, body building and “fat burning”. In 2004, Hydroxycut products containing ephedra were withdrawn from use in the United States because of cardiovascular risks and in 2009 because of hepatotoxicity. Nevertheless, Hydroxycut products with different ingredients are still commercially available and have continued to be implicated in cases of clinically apparent acute liver injury.|SLIMQUICK is a popular, proprietary line of multi-ingredient nutritional supplements (MINS) marketed as weight loss products and sold widely in pharmacies and grocery stores as well on the internet. The major ingredients in the products include green tea extract, caffeine and various herbal, fruit and vegetable extracts. There have been rare reports of clinically apparent liver injury in patients taking SLIMQUICK products, the majority of which had clinical features suggestive of green tea hepatotoxicity.

Herbal and Dietary Supplements

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)|Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)|Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved. (See all compounds classified as Antimutagenic Agents.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

(-)-Epigallocatechin gallate has known human metabolites that include (-)-Epigallocatechin gallate, 3p-hydroxy-glucuronide and (-)-Epigallocatechin gallate, 4p-hydroxy-glucuronide.

EGCG cpd

Epigallocatechin gallate Use and Manufacturing

Uses

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

Polyketides [PK] -> Flavonoids [PK12] -> Proanthocyanidins [PK1203]

Computed Properties

Molecular Weight:458.4
XLogP3:1.2
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:4
Exact Mass:458.08491139
Monoisotopic Mass:458.08491139
Topological Polar Surface Area:197
Heavy Atom Count:33
Complexity:667
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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