Hexahydroxydiphenic acid

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Hexahydroxydiphenic acid
Hexahydroxydiphenic acid.svg
Names
Preferred IUPAC name
4,4′,5,5′,6,6′-Hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylic acid
Other names
HHDP
3,4,5,3′,4′,5′-Hexahydroxydiphenate
3,4,5,3′,4′,5′-Hexahydroxydiphenic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24) X mark.svgN
    Key: MFTSECOLKFLUSD-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24)
    Key: MFTSECOLKFLUSD-UHFFFAOYAZ
  • O=C(O)c2cc(O)c(O)c(O)c2c1c(O)c(O)c(O)cc1C(=O)O
Properties
C14H10O10
Molar mass 338.224 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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Hexahydroxydiphenic acid is an organic compound with the formula [(HO)3C6HCO2H]2. It is the oxidatively coupled derivative of gallic acid [2] It is a white solid, although samples are typically brown owing to oxidation.

Contents

Occurrence

Ellagic acid. Ellagic acid.svg
Ellagic acid.

Luteic acid and ellagic acid are the mono- and dilactone of hexahydroxydiphenic acid, respectively. Hexahydroxydiphenic acid is a component of some ellagitannins, [3] such as casuarictin.

See also

Related Research Articles

<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">Pyrogallol</span> Benzene-1,2,3-triol

Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols.

The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.

<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

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

Chebulagic acid is a benzopyran tannin and an antioxidant that has many potential uses in medicine.

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

Ethyl gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant.

1-<i>alpha</i>-<i>O</i>-Galloylpunicalagin Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate and in Combretum glutinosum.

<span class="mw-page-title-main">Ellagitannin</span> Diverse class of hydrolyzable tannins, a type of polyphenol

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

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

Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.

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

Punigluconin is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Emblica officinalis. It is a molecule having a hexahydroxydiphenic acid group and two gallic acids attached to a gluconic acid core.

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

Lambertianin C is an ellagitannin.

<span class="mw-page-title-main">Sanguiin H-6</span> Chemical compound

Sanguiin H-6 is an ellagitannin.

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

Alnusiin is an ellagitannin found in Alnus sieboldiana.

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

Geraniin is a dehydroellagitannin found in geraniums. It is found for instance in Geranium thunbergii, which is one of the most popular folk medicines and also an official antidiarrheic drug in Japan. It can also be found in the rind of Nephelium lappaceum (rambutan).

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

Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid.

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

Nupharin A is an ellagitannin found in Nuphar japonica. It is a molecule with three gallic acid units and one hexahydroxydiphenic acid unit attached to a glucose residue. It is an isomer of punicafolin and tellimagrandin II.

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

Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid.

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

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.

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

Dehydrohexahydroxydiphenic acid is a group found in dehydroellagitannins. It is formed from hexahydroxydiphenic acid (HHDP) through oxidation of the plant hydrolysable tannins. It is found in ellagitannins such as euphorbin A, geraniin or mallotusinic acid.

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

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus. This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

References

  1. ↑ "MetaCyc hexahydroxydiphenic acid". biocyc.org.
  2. ↑ Haslam, E.; Cai, Y. (1994). "Plant polyphenols (vegetable tannins): Gallic acid metabolism". Natural Product Reports. 11 (1): 41–66. doi:10.1039/NP9941100041. PMID   15206456.
  3. ↑ Feldman, Ken S.; Iyer, Malliga R.; Liu, Yanze (2003). "Ellagitannin Chemistry. Studies on the Stability and Reactivity of 2,4-HHDP-Containing Glucopyranose Systems". The Journal of Organic Chemistry. 68 (19): 7433–7438. doi:10.1021/jo034495x. PMID   12968897.
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