6270. Morindin

Nomenclature

CAS number: 60450-21-7
1,5-Dihydroxy-2-methyl-6-[(6-O-β-d-xylopyranosyl-β-d-glucopyranosyl)oxy]-9,10-anthracenedione; 2-[[6-O-(6-deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-1,5-dihydroxy-6-methyl-9,10-anthracenedione.
C27H30O14; mol wt 578.52.
C 56.05%, H 5.23%, O 38.72%.

Description and references

From bark of Coprosma australis Forst. (C. grandifolia Hook.), Rubiaceae: Briggs, Dacre, J. Chem. Soc. 1948, 564. Structure: Briggs, Le Quesne, ibid. 1963, 3471. On acid hydrolysis yields the aglucone morindone. Synthesis and structure proof: B. Vermes et al., Phytochemistry 19, 119 (1980).

Chemical structure

Properties

Yellow needles from glacial acetic acid, mp 169-171°. [α]D20 -90.0° (c = 0.054 in dioxane). Absorption max (ethanol): 230, 261, 448 nm (log ε 4.15, 3.93, 3.57). Sol in cold water but on boiling forms a water insol form, β-morindin. Sol in dioxane, pyridine, acetone, methanol; slightly sol in ethanol, glacial acetic acid. Practically insol in ether, chloroform, benzene, petr ether.