3,4-Methylenedioxycinnamic acid

Methylenedioxycinnamic acid [2373-80-0] M 192.2, m 243-244°(dec). Crystd from glacial acetic acid. 

Methyl -propyl ketone, 340 Methyl pyridines, purification of, 177-179 N-Methylpyrrole, 837, 838 Methyl red, 621, 625 sodium salt of, 626 Methyl salicylate, 780,782 Methyl sulphite, 304 2-Methylthiophene, 836 Methyl p-toluenesulphonate, 825 Methylurea, 968, 969 Methylene bromide, 300 Methylene chloride, purification of, 176 3 4-Methylenedioxycinnamic acid, 711, 719... 

Synthesis of podophyllotoxin (3.86) in cell culture of Linum album results in yields comparable to those of the most efficient tissue cultures of Podophyllum hexandrum. In order to further improve L. album cultures, Seidel et al. (2002) investigated the biosynthesis of podophyllotoxin (3.86). They fed a number of labeled compounds that to L. album cell cultures to identify which of these compounds could be used as precursors to podophyllotoxin. They determined that the substitution pattern on the benzene ring is critical. The substitution has to be either 3-methoxy, 4-hydroxy, as in ferulic acid (3.33), or, alternatively, 3,4-methylenedioxycinnamic acid (3.90) can serve as precursor. The precursor of podophyllotoxin in L. album appears to be deoxypodophyllotoxin (3.83), based on the higher level of isotope incorporation in the latter compound. This means that 7-hydroxymatairesinol, the precursors of 5-methoxypodophyllotoxin in L. flavum (Xia et al., 2000), is not a precursor of podophyllotoxin in L. album. 

A-Methyl-3,4-dihydroxyphenylalanine has been prepared by methylation of a-acetamino-3,4-methylenedioxycinnamic acid, followed by reduction and hydrolysis of the product 2 and by a method similar to that outlined above. ... 

Dichloro-substituted, methylenedioxy-substituted, or sulfur-containing planar aromatic molecules often crystallize in 3 structures. These effects were utilized to design [2-1-2] photoreactive molecular complexes [30]. Cocrystallization from EtOH of 6-chloro-3,4-methylenedioxycinnamic acid with 2,4-dichlorocin-namic acid and with 3,4-dichlorocinnamic acid (all three cinnamic acids are 13-type [2-1-2] photoreactive crystals) gave the 2 1 and 1 1 complexes, respectively. Irradiation of these complexes yielded mixtures of three P-truxinic dimers in a statistical ratio (Scheme 9). This result, together with the crystal structures of the component acids, indicates that each sheet that is stabilized by an interstack... 

Another study (84JHC1183) was prompted by the value of ester derivatives as storable but ready sources of 5,6-dihydroxyindole 1 for biological studies (67NAT190) (67JPS1019), and focused on the synthesis of the cyclic carbonate derivative 19 (Scheme 8). This procedure starts from 3,4-methylenedioxycinnamic acid and utilizes thermal decomposition of an azide intermediate, produced from a... 

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