Hexahydroxydiphenic acid

{{Short description|Oxidatively coupled derivative of gallic acid}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 441140894

| Name = Hexahydroxydiphenic acid

| ImageFile = hexahydroxydiphenic acid.svg

| ImageName = Chemical structure of hexahydroxydiphenic acid

| ImageAlt = Chemical structure of hexahydroxydiphenic acid

| PIN = 4,4′,5,5′,6,6′-Hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylic acid

| OtherNames = HHDP
3,4,5,3′,4′,5′-Hexahydroxydiphenate
3,4,5,3′,4′,5′-Hexahydroxydiphenic acid

|Section1={{Chembox Identifiers

| CASNo = 128785-08-0

| CASNo_Ref = {{cite web |title=MetaCyc hexahydroxydiphenic acid |url=https://biocyc.org/compound?orgid=META&id=CPD-17774 |website=biocyc.org}}

| PubChem = 10315050

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8490515

| SMILES = O=C(O)c2cc(O)c(O)c(O)c2c1c(O)c(O)c(O)cc1C(=O)O

| 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)

| InChIKey = MFTSECOLKFLUSD-UHFFFAOYAZ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MFTSECOLKFLUSD-UHFFFAOYSA-N

| MeSHName =

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|Section2={{Chembox Properties

| C=14 | H=10 | O=10

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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{{Cite journal | last1 = Haslam | first1 = E. | last2 = Cai | first2 = Y. | doi = 10.1039/NP9941100041 | title = Plant polyphenols (vegetable tannins): Gallic acid metabolism | journal = Natural Product Reports | volume = 11 | issue = 1 | pages = 41–66 | year = 1994 | pmid = 15206456}} It is a white solid, although samples are typically brown owing to oxidation.

Occurrence

file:Ellagic acid.svg.]]

Luteic acid and ellagic acid are the mono- and dilactone of hexahydroxydiphenic acid, respectively. Hexahydroxydiphenic acid is a component of some ellagitannins,{{cite journal | doi = 10.1021/jo034495x| pmid = 12968897| title = Ellagitannin Chemistry. Studies on the Stability and Reactivity of 2,4-HHDP-Containing Glucopyranose Systems| journal = The Journal of Organic Chemistry| volume = 68| issue = 19| pages = 7433–7438| year = 2003| last1 = Feldman| first1 = Ken S.| last2 = Iyer| first2 = Malliga R.| last3 = Liu| first3 = Yanze}} such as casuarictin.

See also

References

{{reflist}}

{{Ellagitannin}}

{{DEFAULTSORT:Hexahydroxydiphenic Acid}}

Category:Ellagitannins

Category:Pyrogallols

Category:Biphenyls

Category:Trihydroxybenzoic acids

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