Luteic acid

Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid.^[1] It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.^[2]

Luteic acid

Names
Preferred IUPAC name 3,4,8,9,10-Pentahydroxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylic acid
Other names Luteolic acid
Identifiers
CAS Number	476-67-5
3D model (JSmol)	Interactive image
ChemSpider	4477499
PubChem CID	5319108
UNII	B54CJS6VNV Y
CompTox Dashboard (EPA)	DTXSID90197216
InChI InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21) Key: FLZGFQFYDGHWLR-UHFFFAOYSA-N InChI=1/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21) Key: FLZGFQFYDGHWLR-UHFFFAOYAI
SMILES C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)O)O)O)OC2=O
Properties
Chemical formula	C14H8O9
Molar mass	320.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. Nierenstein, M.; Potter, J. (1945). "The distribution of myrobalanitannin". The Biochemical Journal. 39 (5): 390–392. doi:10.1042/bj0390390. PMC 1258254. PMID 16747927.
2. Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, INIST 19467830 (abstract)