6674. Nomilin

Nomenclature

CAS number: 1063-77-0
1-(Acetyloxy)-1,2-dihydroobacunoic acid ε-lactone; 1-(3-furyl)decahydro-11-hydroxy-4b,7,7-11a,13a-pentamethyloxireno(4,4a)-2-benzopyrano[6,5-g](2)benzoxepin-3,5,9(3aH,4bH,6H)-trione acetate.
C28H34O9; mol wt 514.56.
C 65.36%, H 6.66%, O 27.98%.

Description and references

Bitter principle from citrus juice, seeds. Isoln: O. H. Emerson, J. Am. Chem. Soc. 70, 545 (1948). Structure elucidation: D. L. Dreyer, Tetrahedron 21, 75 (1965); idem, ibid. 24, 3273 (1968). Distribution in citrus seeds: S. Hasegawa et al., J. Agric. Food Chem. 28, 922 (1980); R. L. Rouseff, S. Nagy, Phytochemistry 21, 85 (1982). Identification in grapefruit juice: R. L. Rouseff, J. Agric. Food Chem. 30, 504 (1982). Reduction of nomilin bitterness by Arthrobacter globiformis cells: S. Hasegawa, V. A. Pelton, ibid. 31, 178 (1983); by Cornebacterium fascians: S. Hasegawa et al., ibid. 32, 457 (1984); eidem, J. Food Sci. 50, 330 (1985). Antifeedant effect against Spodoptera frugiperda: M. A. Altieri et al., Prot. Ecol. 6, 91 (1984). Biosynthetic pathways: S. Hasegawa et al., Phytochemistry 23, 1601 (1984).

Chemical structure

Properties

Needles from methanol, mp 278-279°. Slightly sol in 2-propanol, ethyl acetate. [α]D23 -95.7°.