Enantiomeric 3-hydroxypent-4-enethionamides from thioglucosides of Crambe and Brassica seeds by action of ferrous salts

1968 ◽  
Vol 46 (9) ◽  
pp. 1507-1512 ◽  
Author(s):  
F. L. Austin ◽  
C. A. Gent ◽  
I. A. Wolff
Keyword(s):  
Brassica Napus ◽  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Seed Meal ◽  
Optical Rotatory ◽  
Crambe Abyssinica ◽  
Magnetic Resonance Studies ◽  
Derivatives Of

epi-Progoitrin, the major thioglucoside of Crambe abyssinica seed, is cleaved by ferrous salts to yield (S)-1-cyano-2-hydroxy-3-butene and (S)-3-hydroxypent-4-enethionamide. The products are the same whether obtained from the purified thioglucoside or from the seed meal. Identical behavior was observed for seed meal of Brassica napus, which gave corresponding derivatives of the opposite configuration. Optical rotatory dispersion and proton magnetic resonance studies suggest the existence of solvent-dependent differences in rotamer composition for the 3-hydroxypent-4-enethionamides.

Rapeseed meal autolysis. Formation of diastereomeric (2R)-1-cyano-2-hydroxy-3,4-epithiobutanes from progoitrin

1967 ◽  
Vol 45 (17) ◽  
pp. 1971-1974 ◽  
Author(s):  
M. E. Daxenbichler ◽  
C. H. VanEtten ◽  
W. H. Tallent ◽  
I. A. Wolff
Keyword(s):  
Brassica Napus ◽  
Rapeseed Meal ◽  
Chiral Center ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Seed Meal ◽  
Optical Rotatory ◽  
Brassica Napus L ◽  
Crambe Abyssinica ◽  
Dispersion Data

When defatted seed from Brassica napus L. var. Regina II (a rapeseed) was autolyzed, its major thioglucoside (progoitrin) underwent degradation analogous to that for epiprogoitrin in Crambe abyssinica seed meal. Depending on the conditions, (R)-1-cyano-2-hydroxy-3-butene and the diastereomeric forms of (2R)-1-cyano-2-hydroxy-3,4-epithiobutane were formed in autolyzed B. napus meal instead of (S)-goitrin. The configuration at the chiral center containing the hydroxyl is assigned on the basis of known data. The configuration at carbon 3 of the episulfides is predicted on the basis of the optical rotatory dispersion data.

Lignans and related phenols. Part IX. Observations on the spectroscopic characterization and conformational analysis of apo-compounds of the arylnaphthalene class

1969 ◽  
Vol 47 (11) ◽  
pp. 2075-2080 ◽  
Author(s):  
D. C. Ayres
Keyword(s):  
Magnetic Resonance ◽  
Conformational Analysis ◽  
Proton Magnetic Resonance ◽  
Spectroscopic Characterization ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory

The need for further spectroscopic characterization of apo-compounds of type 1 is discussed and details of proton magnetic resonance (p.m.r.) and optical rotatory dispersion (o.r.d.) spectra are given. Analysis of these spectra is relevant to the assignment of structure to the recently isolated thomasic acid and also reveals unusual conformational features in compounds of this group.

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