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
  • 128785-08-0 [1]
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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Infobox references

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.

Ellagic acid. Ellagic acid.svg
Ellagic acid.

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

See also

Related Research Articles

Gallic acid 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".

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Ellagic acid Natural phenol antioxidant

Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables. Ellagic acid is the dilactone of hexahydroxydiphenic acid. There is no scientific evidence that consuming ellagic acid has any beneficial effect on human health or prevents diseases.

2-Iodoxybenzoic acid Chemical compound

2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is prepared from 2-iodobenzoic acid, potassium bromate, and sulfuric acid. Frigerio and co-workers have also demonstrated, in 1999 that potassium bromate may be replaced by commercially available Oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. In the past, it was believed that IBX was shock sensitive, but it was later proposed that samples of IBX were shock sensitive due to the residual potassium bromate left from its preparation. Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid.

Electrosynthesis in chemistry is the synthesis of chemical compounds in an electrochemical cell. Compared to ordinary redox reaction, electrosynthesis sometimes offers improved selectivity and yields. Electrosynthesis is actively studied as a science and also has industrial applications. Electro-oxidation has potential for wastewater treatment as well.

Chebulagic acid Chemical compound

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

Ethyl gallate 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.

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.

Casuarictin Chemical compound

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

Roburin A Chemical compound

Roburin A is a tannin found in oak wood or oak cork.

Punigluconin 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.

Sanguiin H-6 Chemical compound

Sanguiin H-6 is an ellagitannin.

Alnusiin Chemical compound

Alnusiin is an ellagitannin found in Alnus sieboldiana.

Geraniin 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).

Sanguisorbic acid 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.

Methyl gallate Chemical compound

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

Urolithin A 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, and walnuts. Since the 2000s, urolithin A has been the subject of preliminary studies regarding its possible biological effects.

Dehydrohexahydroxydiphenic acid 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.

Tellimagrandin I Chemical compound

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

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.