Flavogallonic acid dilactone

Flavogallonic acid dilactone
Names

Preferred IUPAC name 3,4,5-Trihydroxy-2-(1,6,7-trihydroxy-4,9-dioxo-4,9-dihydro[1]benzopyrano[5,4,3-cde][1]benzopyran-2-yl)benzoic acid
Identifiers
CAS Number	103744-88-3^Y
3D model (JSmol)	Interactive image
PubChem CID	71308199
CompTox Dashboard (EPA)	DTXSID70745436
InChI InChI=1S/C21H10O12/c22-8-2-5(19(28)29)10(16(27)14(8)25)4-1-6-11-12-7(21(31)32-17(11)13(4)24)3-9(23)15(26)18(12)33-20(6)30/h1-3,22-27H,(H,28,29) Key: ICEBGCDIMFYRLU-UHFFFAOYSA-N
SMILES O=c4oc3c1c(c(c2O)oc(=O)c1cc(O)c3O)c4cc2-c(c(O)c5O)c(C(O)=O)cc5O
Properties
Chemical formula	C₂₁H₁₀O₁₂
Molar mass	454.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Flavogallonic acid dilactone is a hydrolysable tannin that can be found in Rhynchosia volubilis seeds,^[1] in Shorea laevifolia,^[2] in Anogeissus leiocarpus and Terminalia avicennoides.^[3]

References

^ Antiproliferative constituents in the plant 8. Seeds of Rhynchosia volubilis. Kinjo Junei, Nagao Tsuneatsu, Tanaka Takashi, Nonaka Gen-Ichiro and Okabe Hikaru, Biological & pharmaceutical bulletin, 2001, vol. 24, no12, pp. 1443-1445, INIST 13400364, doi:10.1248/bpb.24.1443
^ 5A-Reductase inhibitory tannin-related compounds isolated from Shorea laevifolia. Yoshio Hirano, Ryuichiro Kondo and Kokki Sakai, Journal of wood science, Volume 49, Number 4, pp. 339-343, doi:10.1007/s10086-002-0481-y
^ The use of microfluorometric method for activity-guided isolation of antiplasmodial compound from plant extracts. M. N. Shuaibu, P. A. Wuyep, T. Yanagi, K. Hirayama, T. Tanaka and I. Kouno, Parasitol Res (2008) 102, pp. 1119–1127, doi:10.1007/s00436-008-0879-6

Types of hydrolysable tannins

Carbohydrates

Glucose
Quinic acid
Shikimic acid

Phenolic

gallic acid | Ellagic acid | Vanillic acid

Types

unclassified

1,2-di-O-galloyl-3-O-digalloyl-4,6-O-(S)-hexa- hydroxydiphenoy-β-D-glucose
2,3-(S)-Hexahydroxydiphenoyl-D-glucose
Alienanin B
Alunusnin A
Aromatinin A
Balanophotannin D, E, F and G
Burkinabin A, B and C
Castavaloninic acid
Cinchotannic acid
Cocciferin D2
Emblicanins (Emblicanin A and Emblicanin B)
Euprostin A
Flavogallonic acid
Flavogallonic acid dilactone
Heterophylliin D
Helioscopin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(R)-elaeocarpusinoyl-3-O-galloyl-β-D-glucose)
Helioscopin B (1,3,6-tri-O-galloyl-2,4-(R)-elaeocarpusinoyl-β-D-glucose)
Helioscopinin A (1,6-(S)-hexahydroxydiphenoyl-2,4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose)
Helioscopinin B (1,6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose)
Hipophaenin D
Isostrictinin
Kinotannic acid
Platycaryanin A
Rugosin C, D and F
Squarrosanin A
Strictinin
Syzyginin A
Tannic acid
Tellimagrandin I
Tercatin
Tergallagin
Vescalin
Vescavaloneic acid/Castavaloneic acid