Names | |
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IUPAC name (2R,3R)-3′,4′,5,5′,7-Pentahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate | |
Systematic IUPAC name (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate | |
Other names (-)-Epigallocatechin gallate (2R,3R)-3′,4′,5,5′,7-pentahydroxyflavan-3-yl gallate | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.111.017 |
KEGG | |
MeSH | Epigallocatechin+gallate |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C22H18O11 | |
Molar mass | 458.372 g/mol |
soluble (5 g/L)[ vague ] [1] | |
Solubility | soluble in ethanol, DMSO, dimethyl formamide [1] at about 20 g/L [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.
EGCG – the most abundant catechin in tea – is a polyphenol under basic research for its potential to affect human health and disease. EGCG is used in many dietary supplements.
It is found in high content in the dried leaves of green tea (7380 mg per 100 g), white tea (4245 mg per 100 g), and in smaller quantities, black tea (936 mg per 100 g). [3] During black tea production, the catechins are mostly converted to theaflavins and thearubigins via polyphenol oxidases.[ which? ] [4]
Trace amounts are found in apple skin, plums, onions, hazelnuts, pecans, and carob powder (at 109 mg per 100 g). [3]
When taken orally, EGCG has poor absorption even at daily intake equivalent to 8–16 cups of green tea, an amount causing adverse effects such as nausea or heartburn. [5] After consumption, EGCG blood levels peak within 1.7 hours. [6] The absorbed plasma half-life is ~5 hours, [6] but with majority of unchanged EGCG excreted into urine over 0 to 8 hours. [6] Methylated metabolites appear to have longer half-lives and occur at 8–25 times the plasma levels of unmetabolized EGCG. [7]
Well-studied in basic research, EGCG has various biological effects in laboratory studies. [8] [9] [10] [11]
A 2011 analysis by the European Food Safety Authority found that a cause and effect relationship could not be shown for a link between tea catechins and the maintenance of normal blood LDL-cholesterol concentration. [12] A 2016 review found that high daily doses (107 to 856 mg/day) taken by human subjects over four to 14 weeks produced a small reduction of LDL cholesterol. [13]
A 2018 review showed that excessive intake of EGCG may cause liver toxicity. [14] In 2018, the European Food Safety Authority stated that daily intake of 800 mg or more could increase risk of liver damage. [15]
Taken as a capsule or tablet 338 mg per day of EGCG is considered safe, whereas 704 mg per day is safe if consumed as a tea beverage. [14] 100 mL of green tea contains about 70.2 mg of EGCG (about 165 mg per cup). [15]
Over 2008 to 2017, the US Food and Drug Administration issued several warning letters to manufacturers of dietary supplements containing EGCG for violations of the Federal Food, Drug, and Cosmetic Act. Most of these letters informed the companies that their promotional materials promoted EGCG-based dietary supplements in the treatment or prevention of diseases or conditions that cause them to be classified as drugs under the United States code, [16] [17] [18] while another focused on inadequate quality assurance procedures and labeling violations. [19] The warnings were issued because the products had not been established as safe and effective for their marketed uses and were promoted as "new drugs", without approval as required under the Act. [18]
Green tea is a type of tea that is made from Camellia sinensis leaves and buds that have not undergone the same withering and oxidation process which is used to make oolong teas and black teas. Green tea originated in China, and since then its production and manufacture has spread to other countries in East Asia.
Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates".
Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.
Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.
Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.
Nootropics, colloquially brain supplements, smart drugs and cognitive enhancers, are natural, semisynthetic or synthetic compounds which purportedly improve cognitive functions, such as executive functions, attention or memory.
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.
Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.
Theanine, commonly known as L-theanine and sometimes L-gamma-glutamylethylamide or N5-ethyl-L-glutamine, is an amino acid analogue of the proteinogenic amino acids L-glutamate and L-glutamine and is found primarily in particular plant and fungal species. It was discovered as a constituent of green tea in 1949 and isolated from gyokuro leaves in 1950, thus rendering it a natural product. It constitutes about 1–2% of the dry weight of green tea leaves.
Polyphenon is a series of high grade green tea polyphenol extracts manufactured by the Mitsui Norin Co., Ltd. of Japan. The extracts are in part the result of a water based extraction method which begins with green tea leaves, and then involves successive steps which concentrate the catechins thought to be responsible for the health benefits of green tea.
Red yeast rice, red rice koji, red fermented rice, red kojic rice, red koji rice, anka, or angkak, is a bright reddish purple fermented rice, which acquires its color from being cultivated with the mold Monascus purpureus. Red yeast rice is what is referred to as a "koji" in Japanese, meaning "grain or bean overgrown with a mold culture", a food preparation tradition going back to ca. 300 BC. In both the scientific and popular literature in English that draws principally on Japanese traditional use, red yeast rice is most often referred to as "red rice koji." English language articles favoring Chinese literature sources prefer the translation "red yeast rice."
Hydroxytyrosol is an organic compound with the formula (HO)2C6H3CH2CH2OH. It is a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, although samples often turn beige during storage. It is a derivative, formally speaking, of catechol.
Thearubigins are polymeric polyphenols that are formed during the enzymatic oxidation and condensation of two gallocatechins with the participation of polyphenol oxidases during the fermentation reactions in black tea. Thearubigins are red in colour and are responsible for much of the staining effect of tea. Therefore, a black tea often appears red while a green or white tea has a much clearer appearance. The colour of a black tea, however, is affected by many other factors as well, such as the amount of theaflavins, another oxidized form of polyphenols.
Gallocatechol or gallocatechin (GC) is a flavan-3-ol, a type of chemical compound including catechin, with the gallate residue being in an isomeric trans position.
Theaflavin digallate (TFDG) is an antioxidant natural phenol found in black tea, and a theaflavin derivative.
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.
Gallocatechin gallate (GCG) is the ester of gallocatechin and gallic acid and a type of catechin. It is an epimer of epigallocatechin gallate (EGCG).
The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.