trans-4-Methoxy-2,3-methylenedioxycinnamaldehyde:A new aromatic aldehyde from Apium petroselinum seedsN K Anand, (Miss) S Bhanumati & S R Gupta,
Indian Journal of Chemistry Vol. 29B, 187 (1990)Summarytrans-4-Methoxy-2,3-methylenedioxycinnamaldehyde has been isolated from Apium petroselinum seeds besides isoimperatorin, umbelliferone and 4-hydroxycinnamic acid.
In a broad programme in our laboratory on the chemical constituents of
Apium petroselinum1-8, we report herein the isolation and characterization of a new natural product,
trans-4-methoxy-2,3-methylenedioxycinnamaldehyde. In addition 5-O-prenylpsoralin, umbelliferone and 4-hydroxycinnamic acid were also isolated. The structure of the new aldehyde was finally settled by its oxidation
9 with neutral KMnO
4 in the cold acetone to 4-methoxy-2,3-methylenedioxybenzaldehyde
10, mp 78-79°C.
Experimental
Isolation of compounds
The petrol defatted seeds (5 kg) of A. petroselinum were thoroughly extracted with benzene. The benzene extract was concentrated and the residue subjected to column chromatography over silica gel. Successive elution with petrol-benzene (1:1), petrol-benzene (1:3), benzene and benzene-ethyl acetate (19:1) gave trans-4-methoxymethylenedioxycinnamaldehyde, isoimperatorin, umbelliferone and 4-hydroxycinnamic acid respectively as identified from their spectral data and by comparison with authentic samples.
Identification of the new aldehyde
It was obtained as yellowish brown needles (25 mg), mp 138-139°C; Rf 0.56 (acetone-benzene; 1:24). It gave a positive 2,4-DNP test and also a positive sulphuric acid-gallic acid test.
Permanganate oxidation of the new aldehyde
A solution of the aldehyde (5 mg) in dry acetone (1 ml) was treated with neutral KMnO4 (50 mg) in dry acetone (15 ml). The reaction mixture was left at room temperature for 24 hr, manganese dioxide was filtered off and the solvent removed. The residue was dissolved in ether and washed carefully with 20% aq. NaHCO3. The ether solution on standing gave crystals of 4-methoxy-2,3-methylenedioxybenzaldehyde (2 mg), mp and mixed mp 78-79°C.References[1] Garg SK, Gupta S R & Sharma N D, Phytochemistry, 17 (1978)2135.
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[8] Anand N K, Sharma N D & Gupta S R, Nat. Acad. Sci. Lett, 4, 249 (1981)
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Post 247833 (missing)
(Rhodium: "Carpacin isolation & Physical Data", Chemistry Discourse)[10] Campbell K N, Hopper P F & Campbell B K,
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https://www.thevespiary.org/rhodium/Rhodium/pdf/methylenedioxymethoxybenzaldehydes.pdf)