Luteic acid

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Luteic acid

IUPAC name 3,4,8,9,10-pentahydroxy-6-oxobenzo[c]chromene-1-carboxylic acid
Other names Luteolic acid
Identifiers
CAS number	476-67-5
PubChem	5319108
	Jmol-3D images	Image 1
SMILES C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)O)O)O)OC2=O
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
Properties
Molecular formula	C₁₄H₈O₉
Molar mass	320.21 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]

References

↑ Nierenstein, M.; Potter, J. (1945). "The distribution of myrobalanitannin". The Biochemical journal 39 (5): 390–392. PMID 21020785.
↑ 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)

External links

Types of ellagitannins

Aglycones

Lactones

Ellagic acid
Gallagic acid
Gallagic acid dilactone
Luteic acid
Sanguisorbic acid dilactone
Tergallic acid dilactone
Valoneic acid dilactone

Monomers

Acetonyl geraniin
Alnusiin
Bicornin
carlesiin
Castalagin (Vescalagin)
Castalin
Casuarictin
Casuariin
Casuarinin
Emblicanin A and B
Euscaphinin
Grandinin
Helioscopinin B
Jolkinin
Lagerstannin A, B and C
Macranganin
Myrobalanitannin
Nupharin A, B, C, D, E and F
Pedunculagin
Galloyl pedunculagin
Phyllanemblinin A, B, C, D, E and F
Punicalin
Roburin B, C, D and E
Rugosin E
Sanguiin H-5
Stenophyllanin A, B and C
Strictinin
Tellimagrandin I and II
Teracatain
Terchebulin
Terflavin A and B

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Alnicortin
Euphorbin A
Euphorscopin
Excoecarianin
Geraniin
Granatin A and B
Helioscopinin A
Mallotusinic acid
Supinanin
Terchebin

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic acid

molecules with Elaeocarpusinic acid	Elaeocarpusin Helioscopin B Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)

Oligomers

Dimers: Agrimoniin; Cornusiin E (dimer of tellimagrandin II); Lambertianin A and B; Nobotanin B; Roburin A; Sanguiin H-6

Trimers: Lambertianin C; Raspberry ellagitannin

Tetramers: Lambertianin D; Nobotanin S

Pentamer: Melastoflorin A

Other

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