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

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

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=
PubChem	127406
ChemSpider	23171208^Y
ChEMBL	CHEMBL310527^Y
Jmol-3D images	Image 1 Image 2
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
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
Properties
Molecular formula	C₂₈H₂₄O₁₈
Molar mass	648.48 g mol⁻¹
Exact mass	648.096264 u
Density	1.98g/cm³
Boiling point	1114.4 °C @ 760mmHg
Hazards
Flash point	364.6
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

^ ^a ^b 3,4,5-tri-O-galloylquinic acid on home.ncifcrf.gov
^ Bouchet N., Levesque J., Bodo B. and Pousset J-L. (1998). "3,4,5-tri-O-galloylquinic acid ethyl ester from Guiera senegalensis". Pharmaceutical Biology 36 (1): 63–65. http://cat.inist.fr/?aModele=afficheN&cpsidt=2444951.
^ 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. John P. Moore, Kim L. Westall, Neil Ravenscroft, Jill M. Farrant, George G. Lindsey and Wolf F. Brandt, Biochem J. 2005 January 1; 385(Pt 1), pp. 301–308, doi:10.1042/BJ20040499, PMC PMC1134698
^ PubChem 127406

Types of gallotannins

Aglycones	Digallic acid \| Gallic acid \| Vanillic acid

Examples	Burkinabin A \| B \| C \| Galloyl glucose \| Digalloyl glucose \| Trigalloyl glucose: 1,2,6-Trigalloyl glucose / 1,3,6,-Trigalloyl glucose (Corilagin) \| Tetragalloyl glucose: 1,2,3,6-tetragalloylglucose \| Pentagalloyl glucose: 1,2,3,4,6-pentagalloyl-glucose and 6-digalloyl-1,2,3-trigalloyl-glucose \| Hexagalloyl glucose \| Heptagalloyl glucose \| Octagalloyl glucose \| Nonagalloyl glucose \| Decagalloyl glucose \| 1,3,4-Tri-O-galloylquinic acid \| 3,4,5-Tri-O-galloylquinic acid \| 3,5-di-O-galloyl-shikimic acid \| 3,4,5-tri-O-galloylshikimic acid \| 1,2,6-trigalloyl alloside \| 1,3,6-trigalloyl alloside \| 1,2,3,6-tetragalloyl alloside