Digallic acid
Names
Preferred IUPAC name
3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoic acid
Other names
Digallate
3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate
m-digallic acid
Digalloyl ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.842
UNII
  • 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) ☒N
    Key: COVFEVWNJUOYRL-UHFFFAOYSA-N ☒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
  • C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)[O-]
  • O=C(O)c2cc(O)c(O)c(OC(=O)c1cc(O)c(O)c(O)c1)c2
Properties
C14H10O9
Molar mass 322.225 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

Digallic acid is a polyphenolic compound found in Pistacia lentiscus.[1] Digallic acid is also present in the molecule of tannic acid.[2] Digalloyl esters involve either -meta, or -para depside bonds.[3]

Tannase is an enzyme that uses digallate to produce gallic acid. This enzyme can also be used to produce digallic acid from gallotannins.[4]

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ Ann E. Hagerman. "The Tannin Handbook". Miami University.
  4. ↑ 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.


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