Gallocatechol

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Gallocatechol
(+)-Gallocatechin.svg
Gallocatechol 3D BS.png
Names
Other names
(+)-gallocatechin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Gallocatechol
PubChem CID
UNII
  • 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+/m0/s1 X mark.svgN
    Key: XMOCLSLCDHWDHP-SWLSCSKDSA-N X mark.svgN
  • InChI=1/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+/m0/s1
    Key: XMOCLSLCDHWDHP-SWLSCSKDBQ
  • C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
Properties
C15H14O7
Molar mass 306.270 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Contents

This compound possesses two epimers. The most common, (+)-gallocatechin (GC), CAS number 970-73-0, is found notably in green tea. The other enantiomer is called (-)-gallocatechin or ent-gallocatechin. It was first isolated from green tea by Michiyo Tsujimura in 1934. [1]

Epigallocatechin is another type of catechin, with the gallate residue being in an isomeric cis position. It can be found in St John's wort. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Green tea</span> Unoxidized tea

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.

<span class="mw-page-title-main">Gallic acid</span> 3,4,5-Trihydroxybenzoic acid

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".

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Flavan-3-ol</span> Category of polyphenol compound

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.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

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.

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.

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.

<span class="mw-page-title-main">Epigallocatechin gallate</span> Catechin (polyphenol) in tea

Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

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.

<span class="mw-page-title-main">Prodelphinidin</span>

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.

The molecular formula C22H18O11 (molar mass: 458.37 g/mol, exact mass: 458.084911) may refer to:

<span class="mw-page-title-main">Tricetinidin</span> Chemical compound

Tricetinidin is an intense red-colored chemical compound belonging to the 3-deoxyanthocyanidins. It can be found in black tea infusions. Tricetinidin, in tea, would be a product of the oxidative degallation of epigallocatechin gallate (EGCG).

<span class="mw-page-title-main">Epicatechin gallate</span> Chemical compound

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape.

Prorobinetidins are a type of condensed tannins formed from robinetinidol. They form robinetinidin when depolymerized under oxidative conditions.

<span class="mw-page-title-main">Gallocatechin gallate</span> Chemical compound

Gallocatechin gallate (GCG) is the ester of gallocatechin and gallic acid and a type of catechin. It is an epimer of epigallocatechin gallate (EGCG).

<span class="mw-page-title-main">Phenolic content in tea</span> Natural plant compounds

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.

<span class="mw-page-title-main">Sinecatechins</span>

Sinecatechins is a specific water extract of green tea leaves from Camellia sinensis that is the active ingredient in an ointment approved by the FDA in 2006 as a botanical drug to treat genital warts. Sinecatechins are mostly catechins, 55% of which is epigallocatechin gallate. It was the first botanical drug approved by the US FDA.

<span class="mw-page-title-main">Michiyo Tsujimura</span> Japanese agricultural and biochemist (1888–1969)

Michiyo Tsujimura was a Japanese agricultural scientist and biochemist whose research focused on the components of green tea. She was the first woman in Japan to receive a doctoral degree in agriculture.

<span class="mw-page-title-main">Theasinensin A</span> Chemical compound

Theasinensin A is polyphenol flavonoid from black tea created during fermentation, by oxidation of epigallocatechin gallate.

References

  1. "Michiyo Tsujimura (1888–1969)". Ochanomizu University. Archived from the original on 21 November 2015. Retrieved 10 November 2015.
  2. Wei, Yun; Xie, Qianqian; Dong, Wanting; Ito, Yoichiro (2009). "Separation of epigallocatechin and flavonoids from Hypericum perforatum L. By high-speed counter-current chromatography and preparative high-performance liquid chromatography". Journal of Chromatography A. 1216 (19): 4313–4318. doi:10.1016/j.chroma.2008.12.056. PMC   2777726 . PMID   19150073.