Chondrocurine

Title: Chondrocurine
CAS Registry Number: 477-58-7
CAS Name: 6,6¢-Dimethoxy-2,2¢-dimethyltubocuraran-7¢,12¢-diol
Additional Names: d-chondocurine; d-tubocurine
Molecular Formula: C36H38N2O6
Molecular Weight: 594.70
Percent Composition: C 72.71%, H 6.44%, N 4.71%, O 16.14%
Literature 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).
Properties: Slender needles from methanol, mp 232-234°; also reported as mp 218-220° (Boissier). [a]D24 +200° (c = 0.5 in 0.1N HCl). [a]D24 +105° (c = 0.9 in pyridine).
Melting point: mp 232-234°; mp 218-220° (Boissier)
Optical Rotation: [a]D24 +200° (c = 0.5 in 0.1N HCl); [a]D24 +105° (c = 0.9 in pyridine)
Derivative Type: Sulfate tetrahydrate
Molecular Formula: C36H38N2O6.H2SO4.4H2O
Molecular Weight: 764.84
Percent Composition: 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). [a]D24 +184° (c = 0.375 in methanol).
Melting point: mp 263-265° (dec)
Optical Rotation: [a]D24 +184° (c = 0.375 in methanol)
Derivative Type: Methiodide
Properties: mp 270-275°.
Melting point: mp 270-275°
Derivative Type: Dimethiodide
Molecular Formula: C38H44I2N2O6
Molecular Weight: 878.57
Percent Composition: C 51.95%, H 5.05%, I 28.89%, N 3.19%, O 10.93%
Properties: Pale amorphous precipitate, mp 275° (dec). [a]D24 +184° (c = 0.375 in methanol). uv max (water): 225, 280 nm (e 62000, 7030).
Melting point: mp 275° (dec)
Optical Rotation: [a]D24 +184° (c = 0.375 in methanol)
Absorption maximum: uv max (water): 225, 280 nm (e 62000, 7030)
Use: Methiodides have curarizing power.
Chondrofoline Chondroitin Sulfate Chondrosine Chonemorphine Chorionic Gonadotropin