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

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

IUPAC name (1S,3R,4S,5R)-1-Hydroxy-3,4,5-tris((3,4,5-trihydroxybenzoyl)oxy)cyclohexanecarboxylic acid
Other names TGQA (3R,5R)-1-Hydroxy-3,4,5-tris(3,4,5-trihydroxyphenylcarbonyloxy)cyclohexanecarboxylic acid
Identifiers
CAS Number	99745-62-7^N
ChEMBL	ChEMBL310527^Y
ChemSpider	23171208^Y
Jmol interactive 3D	Image Image
PubChem	127406
InChI 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^Y Key: PEOHIPMSHPWYAQ-LGFATHPOSA-N^Y 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
SMILES 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
Chemical formula	C₂₈H₂₄O₁₈
Molar mass	648.48 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).
N verify (what is ^YN ?)
Infobox references

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 2 3,4,5-tri-O-galloylquinic acid on home.ncifcrf.gov
↑ 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. doi:10.1076/phbi.36.1.63.4624.
↑ 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.
↑ CID 127406 from PubChem

Types of gallotannins

Aglycones

Galloyl glucoses

1-Galloyl glucose Glucogallin

Digalloyl glucoses:	1,6-Digalloyl glucose 2,6-Digalloyl glucose 3,6-digalloyl glucose

Trigalloyl glucoses:	1,2,3-Trigalloyl glucose 1,2,3-tri-O-galloyl-β-D-glucose 1,2,6-Trigalloyl glucose / 1,3,6-Trigalloyl glucose

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:	1,2,3,4,6-Pentagalloyl-glucose 6-digalloyl-1,2,3-trigalloyl-glucose

other	Hexagalloyl glucose Heptagalloyl glucose Octagalloyl glucose Nonagalloyl glucose Decagalloyl glucose

Galloyl quinic acids

Galloyl quinic acids:	3-O-Galloylquinic acid theogallin 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:	1,3,4-Tri-O-galloylquinic acid 3,4,5-Tri-O-galloylquinic acid

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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