Mallojaponin

Mallojaponin
Names

IUPAC name 3,4,5-Trihydroxy-2-({(1'R,3R,3aS,4'R,5'S,6S,6aR,23'R,25'S,26'R,35'R,36'R,37'R)-3a,6,11',12',15',16',17',31',32',36',37'-undecahydroxy-2,2',7',20',28',41'-hexaoxo-25'-[(3,4,5-trihydroxybenzoyl)oxy]-3a, 5,6,6a-tetrahydrospiro[furo[3,2-b]furan-3,39'-[3,6,21,24,27,38,42]heptaoxanonacyclo[35.2.2.133,36.01,35.04,23.05,26.08,13.014,19.029,34]dotetraconta[8,10,12,14,16,18,29,31,33]nonaen]-10' -yl}oxy)benzoic acid
Other names 1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	10276716
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@@H]9O[C@@H]%13COC(=O)c2cc(O)c(O)c(O)c2c4c(O)c(O)c(Oc3c(cc(O)c(O)c3O)C(O)=O)cc4C(=O)O[C@H]%10[C@@H]%13OC(=O)[C@@]7%11CC(=O)[C@@](O)(O[C@]75C(=O)O[C@@H]6[C@@H](O)CO[C@]56O)[C@]%12(O)Oc8c(c(cc(O)c8O)C(=O)O[C@@H]9%10)[C@H]%11%12
Properties
Chemical formula	C₅₄H₃₈O₃₇
Molar mass	1278.86 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus.^[1] This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group (dehydrohexahydroxydiphenic acid or DHHDP) which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

References

↑ Saijo, R; Nonaka, G; Nishioka, I (1989). "Tannins and related compounds. LXXXIV. Isolation and characterization of five new hydrolyzable tannins from the bark of Mallotus japonicus". Chemical & pharmaceutical bulletin. 37 (8): 2063–70. doi:10.1248/cpb.37.2063. PMID 2598308.

Moieties

Lactones

Monomers

C-glycosidic ellagitannins

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

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, B, C and D; Sanguiin H-6

Other

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