2212. Chondrocurine

Nomenclature

CAS number: 477-58-7
6,6′-Dimethoxy-2,2′-dimethyltubocuraran-7′,12′-diol; d-chondocurine; d-tubocurine.
C36H38N2O6; mol wt 594.70.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.

Description and references

Isoln from Chondodendron tomentosum Ruiz & Pav., Menispermaceae: Wintersteiner, Dutcher, Science 97, 467 (1943); King, J. Chem. Soc. 1948, 1945; Bick, Clezy, ibid. 1960, 2402; Boissier et al., Lloydia 28, 191 (1965), C.A. 64, 948b (1966). Structure: Dutcher, J. Am. Chem. Soc. 68, 419 (1946); Hultin, Acta Chem. Scand. 15, 1130 (1961). Configuration: Bick, Clezy, J. Chem. Soc. 1953, 3893; Hultin, Acta Chem. Scand. 17, 753 (1963). Revised structure: Everett et al., Chem. Commun. 1970, 1020. 13C-NMR: L. Koike et al., J. Org. Chem. 46, 2385 (1981).

Chemical structure

Properties

Slender needles from methanol, mp 232-234°; also reported as mp 218-220° (Boissier). [α]D24 +200° (c = 0.5 in 0.1N HCl). [α]D24 +105° (c = 0.9 in pyridine).

Derivative

Sulfate tetrahydrate.
C36H38N2O6.H2SO4.4H2O; mol wt 764.84.
C 56.53%, H 6.33%, N 3.66%, O 29.29%, S 4.19%.

Properties

Rectangular plates from water. Contains 9.43% H2O. After drying, mp 263-265° (dec). [α]D24 +184° (c = 0.375 in methanol).

Derivative

Methiodide.

Properties

mp 270-275°.

Derivative

Dimethiodide.
C38H44I2N2O6; mol wt 878.57.
C 51.95%, H 5.05%, I 28.89%, N 3.19%, O 10.93%.

Properties

Pale amorphous precipitate, mp 275° (dec). [α]D24 +184° (c = 0.375 in methanol). uv max (water): 225, 280 nm (ε 62000, 7030).

Use

Methiodides have curarizing power.