Digallic acid

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
CAS Number
  • 536-08-3 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL366356 ☒N
ChemSpider
  • 334 ☒N
ECHA InfoCard 100.007.842 Edit this at Wikidata
PubChem CID
  • 341
UNII
  • 404KO0584X checkY
CompTox Dashboard (EPA)
  • DTXSID50871747 Edit this at Wikidata
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) ☒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
Chemical formula
 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
Chemical compound

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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Types of gallotannins
Aglycones
Galloyl glucoses
Digalloyl glucoses:
Trigalloyl glucoses:
Tetragalloyl glucoses:
  • 1,2,3,6-tetragalloylglucose
    • 1,2,3,6-tetra-O-galloyl-β-D-glucose
  • 1,2,4,6-Tetragalloyl glucose
    • 1,2,4,6-tetra-O-galloyl-β-D-glucose
Pentagalloyl glucose:
other
  • Hexagalloyl glucose
  • Heptagalloyl glucose
  • Octagalloyl glucose
  • Nonagalloyl glucose
  • Decagalloyl glucose
Galloyl quinic acids
Galloyl quinic acids:
  • 3-O-Galloylquinic acid
  • 4-O-Galloylquinic acid
  • 5-O-Galloylquinic acid
Digalloyl quinic 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
Trigalloyl quinic acids:
Galloyl shikimic acids
  • 4-O-Galloyl shikimic acid
  • 5-O-Galloyl shikimic acid
  • 3,5-di-O-galloyl-shikimic acid
  • 3,4,5-tri-O-galloylshikimic acid
others
  • 1,2,6-trigalloyl alloside
  • 1,3,6-trigalloyl alloside
  • 1,2,3,6-tetragalloyl alloside
  • 1-O-galloyl proto-quercitol
  • 1,4-di-O-galloyl proto-quercitol


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