3387. Djenkolic Acid
Nomenclature
CAS number: 498-59-9
S,S′-Methylenebis-l-cysteine; 3,3′-(methylenedithio)dialanine; 3,3′-methylenedithiobis(2-aminopropanoic acid); l-cysteine thioacetal of formaldehyde. C7H14N2O4S2; mol wt 254.33.
C 33.06%, H 5.55%, N 11.01%, O 25.16%, S 25.22%.
Description and references
An amino acid isolated from the djenkol bean (Pithecolobium lobatum Benth., Leguminosae): van Veen, Hyman, Rec. Trav. Chim. 54, 493 (1935). Synthesis from 1 mol formaldehyde and 2 mols l-cysteine in strong HCl solution: Armstrong, du Vigneaud, J. Biol. Chem. 168, 373 (1947); cf. du Vigneaud, Patterson, ibid. 114, 633 (1936); Middlebrook, Phillips, Biochem. J. 41, 218 (1947). Synthesis of homologs: Frankel, Gertner, J. Chem. Soc. 1960, 898.
Properties
Rosettes of needles of various lengths. Gradually dec between 300 and 350°. [α]D20.5 -65.0° (1.0N HCl); [α]D25 -47.5° (c = 2 in 1.0N HCl). Very sparingly sol in cold water. Soly in boiling water about 1 in 200. Readily sol in aq solns of alkalies or acids.Derivative
Monohydrochloride.Nomenclature
CAS number: 4508-48-9
C7H14N2O4S2.HCl; mol wt 290.79.
C 28.91%, H 5.20%, N 9.63%, O 22.01%, S 22.05%, Cl 12.19%.
Properties
Slender prisms, dec 250-300°. Sol in water.Derivative
Dibenzoyldjenkolic acid.C21H22N2O6S2; mol wt 462.54.
C 54.53%, H 4.79%, N 6.06%, O 20.75%, S 13.86%.