Digallic acid - Misplaced Pages

Digallic acid
Names

Preferred IUPAC name 3,4-Dihydroxy-5-benzoic acid
Other names Digallate 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate m-digallic acid Digalloyl ester
Identifiers
CAS Number	536-08-3
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL366356
ChemSpider	334
ECHA InfoCard	100.007.842
PubChem CID	341
UNII	404KO0584X
CompTox Dashboard (EPA)	DTXSID50871747
InChI InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)Key: COVFEVWNJUOYRL-UHFFFAOYSA-N InChI=1/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)Key: COVFEVWNJUOYRL-UHFFFAOYAG
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O) O=C(O)c2cc(O)c(O)c(OC(=O)c1cc(O)c(O)c(O)c1)c2
Properties
Chemical formula	C₁₄H₁₀O₉
Molar mass	322.225 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Digallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve either -meta, or -para depside bonds.

Tannase is an enzyme that uses digallate to produce gallic acid. This enzyme can also be used to produce digallic acid from gallotannins.

References

Bhouri, W.; Derbel, S.; Skandrani, I.; Boubaker, J.; Bouhlel, I.; Sghaier, M. B.; Kilani, S.; Mariotte, A. M.; Dijoux-Franca, M. G.; Ghedira, K.; Chekir-Ghedira, L. (2010). "Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits". Toxicology in Vitro. 24 (2): 509–515. doi:10.1016/j.tiv.2009.06.024. PMID 19563883.
Delahaye, P.; Verzele, M. (1983). "Analysis of gallic, digallic and trigallic acids in tannic acids by high-performance liquid chromatography". Journal of Chromatography A. 265: 363–367. doi:10.1016/S0021-9673(01)96734-2.
Ann E. Hagerman. "The Tannin Handbook". Miami University.
Nierenstein, M. (1932). "A biological synthesis of m-digallic acid". The Biochemical Journal. 26 (4): 1093–1094. doi:10.1042/bj0261093. PMC 1261008. PMID 16744910.

Types of gallotannins

Aglycones

Galloylglucoses

Monogalloylglucoses:	1-Galloylglucose Glucogallin
Digalloylglucoses:	1,6-Digalloylglucose 2,6-Digalloylglucose 3,6-Digalloylglucose
Trigalloylglucoses:	1,2,3-Trigalloylglucose 1,2,3-Tri-O-galloyl-β-D-glucose 1,2,6-Trigalloylglucose 1,3,6-Trigalloylglucose
Tetragalloylglucoses:	1,2,3,6-Tetragalloylglucose 1,2,3,6-Tetrakis-O-galloyl-β-D-glucose 1,2,4,6-Tetragalloylglucose 1,2,4,6-Tetrakis-O-galloyl-β-D-glucose
Pentagalloylglucoses:	1,2,3,4,6-Pentagalloylglucose 6-Digalloyl-1,2,3-trigalloylglucose
other	Hexagalloylglucose Heptagalloylglucose Octagalloylglucose Nonagalloylglucose Decagalloylglucose

Galloylquinic acids:

Monogalloylquinic acids:	3-O-Galloylquinic acid Theogallin 4-O-Galloylquinic acid 5-O-Galloylquinic acid
Digalloylquinic acids:	1,4-Di-O-galloylquinic acid 3,4-Di-O-Galloylquinic acid 3,5-Di-O-Galloylquinic acid 4,5-Di-O-Galloylquinic acid
Trigalloylquinic acids:	1,3,4-Tri-O-galloylquinic acid 3,4,5-Tri-O-galloylquinic acid

Galloylshikimic acids:

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