3,4,5-Tri-O-galloylquinic acid

3,4,5-Tri-O-galloylquinic acid
Chemical structure of 3,4,5-tri-O-galloylquinic acid
Chemical structure of 3,4,5-tri-O-galloylquinic acid
Names
Preferred IUPAC name
(1S,3R,4S,5R)-1-Hydroxy-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]cyclohexane-1-carboxylic acid
Other names
TGQA
(3R,5R)-1-Hydroxy-3,4,5-tris(3,4,5-trihydroxyphenylcarbonyloxy)cyclohexanecarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C28H24O18/c29-12-1-9(2-13(30)20(12)35)24(38)44-18-7-28(43,27(41)42)8-19(45-25(39)10-3-14(31)21(36)15(32)4-10)23(18)46-26(40)11-5-16(33)22(37)17(34)6-11/h1-6,18-19,23,29-37,43H,7-8H2,(H,41,42)/t18-,19-,23-,28+/m1/s1 checkY
    Key: PEOHIPMSHPWYAQ-LGFATHPOSA-N checkY
  • InChI=1S/C28H24O18/c29-12-1-9(2-13(30)20(12)35)24(38)44-18-7-28(43,27(41)42)8-19(45-25(39)10-3-14(31)21(36)15(32)4-10)23(18)46-26(40)11-5-16(33)22(37)17(34)6-11/h1-6,18-19,23,29-37,43H,7-8H2,(H,41,42)/t18-,19-,23-,28+/m1/s1
    Key: PEOHIPMSHPWYAQ-LGFATHPOBS
  • Key: PEOHIPMSHPWYAQ-LGFATHPOSA-N
  • O[C@]1(C(O)=O)C[C@@H](OC(C2=CC(O)=C(O)C(O)=C2)=O)[C@H](OC(C3=CC(O)=C(O)C(O)=C3)=O)[C@H](OC(C4=CC(O)=C(O)C(O)=C4)=O)C1
  • c1c(c(c(cc1C(=O)O[C@H]2[C@@H]([C@@H](C[C@@](C2)(O)C(=O)O)OC(=O)c3cc(c(c(c3)O)O)O)OC(=O)c4cc(c(c(c4)O)O)O)O)O)O
Properties
C28H24O18
Molar mass 648.482 g·mol−1
Density 1.98g/cm3
Boiling point 1,114.4 °C (2,037.9 °F; 1,387.6 K) at 760mmHg
Hazards
Flash point 364.6 °C (688.3 °F; 637.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3,4,5-Tri-O-galloylquinic acid is a hydrolysable tannin found in Lepidobotrys staudtii,[1] in Guiera senegalensis[2] or in the resurrection plant (Myrothamnus flabellifolius).[3]

It is classified as a natural product with anti-HIV activity[1] and a DNA polymerase inhibitor.[4]

References

  1. ^ a b "3,4,5-tri-O-galloylquinic acid on home.ncifcrf.gov". Archived from the original on 2011-07-16. Retrieved 2010-07-05.
  2. ^ Bouchet, N.; Levesque, J. L.; Bodo, B.; Pousset, J. L. (1998). "3,4,5-Tri-O-Galloylquinic Acid Ethyl Ester from Guiera senegalensis". Pharmaceutical Biology. 36: 63–65. doi:10.1076/phbi.36.1.63.4624.
  3. ^ Westall, K. L.; Moore, J. P.; Ravenscroft, N.; Farrant, J. M.; Lindsey, G. G.; Brandt, W. F. (2005). "The predominant polyphenol in the leaves of the resurrection plant Myrothamnus flabellifolius, 3,4,5 tri-O-galloylquinic acid, protects membranes against desiccation and free radical-induced oxidation". Biochemical Journal. 385 (Pt 1): 301–308. doi:10.1042/BJ20040499. PMC 1134698. PMID 15355309.
  4. ^ CID 127406 from PubChem