Zusammenfassende �bersichtsberichte �ber Hydroxy-zimts�uren und ihre Bedeutung in Lebensmitteln

Herrmann, Karl

doi:10.1007/bf01460618

Cited by 26 publications

(1 citation statement)

References 116 publications

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“…Experiments with thin-layer chromatography (Henkel, 1965) and column chromatography on aluminum oxide with dilute acetic acid as eluent did not give sufficient separation. Herrmann (1967) found p-cumaric acid, ferulic acid, sinapic acid, and caffeic acid in straw. These substances could be expected to pass through the extraction procedures and through the chromatographic procedures like TBA.…”

Section: Resultsmentioning

confidence: 93%

Determination of 2,3,6-trichlorobenzoic acid residues in grain and straw with electron-capture gas chromatography

Mattsson¹,

Kirsten²

1968

J. Agric. Food Chem.

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Section: Resultsmentioning

confidence: 93%

Determination of 2,3,6-trichlorobenzoic acid residues in grain and straw with electron-capture gas chromatography

Mattsson¹,

Kirsten²

1968

J. Agric. Food Chem.

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N‐acylamino acids and peptides I. The synthesis of N‐feruloylamino acids

Pooter

Ali

Sumere

1973

Bulletin des Soc Chimique

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Procedures f o r t h e p r e p a r a t i o n of N-feruloylglycine (11) , -DL-alanine ( X X ) , -DL-valine (XXII) and -G l e u c i n e ( X X I V ) by c l a s s i c a l methods a r e proposed and compared. The s p e c t r a l c h a r a c t e r i s t i c s and Rf-values of t h e s u b s t a n c e s a r e i n c l u d e d . The compounds were s y n t h e s i z e d because N-feruloylamino a c i d s were r e q u i r e d as t e s t s u b s t a m e s d u r i n g a n i n v e s t i g a t i o n i n connection w i t h t h e expected presence of N -f e r u l o y l p r o t e i n s i n b a r l e y [l, 2,3] . Free f e r u l i c a c i d (4-hydroxy-3-methoxycinnamic a c i d ) ( I ) i s wide spread i n n a t u r e [4]. I n a d d i t i o n , t h e compoundo c c u r s a l s o i n bound form, and a b r i e f survey of t h e d i f f e r e n t t y p e s of l i n k a g e s i n which t h e component has s o f a r been i d e n t i f i e d , may be found i n a r e c e n t paper by V a n Sumere e t a1[3]. I n t h e same p u b l i c a t i o n , t h e i d e n t i f i c a t i o n of N-feruloylglycyl-L-phenylalanyl-R, as a n a t u r a l l y o c c u r r i n g sequence of b a r l e y p r o t e i n s , i s d e s c r i b e d . Because N-cinnamoyl-and N-(subs t i t u t e d cinnamoy1)-amino a c i d s and p e p t i d e s were needed as t e s t s u b s t a n c e s d u r i n g t h e i n v e s t i g a t i o n , t h e p r e p a r a t i o n of t h e s e compounds was s t u d i e d . Indeed, l i t t l e i n f o r m a t i o n on s u b s t a n c e s of t h i s group i s a v a i l a b l e i n t h e 1 i t e r a t u r e . B o o t h e t a1 [5] have s y n t h e s i z e d N-feruloylglycine (11) and N-m. coumaroylglycine (1111, while Armstrong e t a1 [6] and Acheson e t a1 [7] have i d e n t i f i e d I1 and N-p.coumaroylglycine ( I V ) i n u r i n e . pounds of t h i s group has n e v e r been d e s c r i b e d . I n t h i s first paper o f a s e r i e s , we t h e r e f o r e propose procedures f o r the s y n t h e s i s of N-feruloylglycine ( I T ) , -DL-alanine ( X X ) , -D G v a l i n e (XXII) and ->leucine ( X X I V ) .However, t o o u r knowledge, t h e p r e p a r a t i o n of o t h e r com--2 4 3 -

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Synthesis of 3‐0‐o.coumaryl‐, 4‐0‐o.coumaryl‐and 3‐0‐ferulyl‐d‐(‐)‐quinic acid. Improved synthesis of 3‐0‐sinapyl‐d‐(‐)‐quinic acid

Pooter¹,

Brucker²,

Sumere³

1976

Bulletin des Soc Chimique

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The title compounds were obtained by a reaction sequence starting from diphenylmethyl 4,5-0-isopropylidenequina$e. Suitably protected cinnamyl chlorides were condensed with this compound, followed by reaction of the intermediate esters with hydrazine hydrate, and then with acetic acid-formic acid-water. The total yields of 3-0-o. As already mentioned in the foregoing paper ( 5 ) . the synthesis of the title compounds by the method proposed by HASLAM et a2 for the synthesis of e.g. 3-O-p.coumaryl-D-(-)-quinicacid (1x)(6), gave rather disheartening results. In fact, the final removal of the protective functions from the easily prepared intermediates (e.g. V I ) required prolonged acidic treatment, entailing heavy losses of material. However, a s this requirement could be explained by the high stability of the employed 1-0-ethoxycarbonyl-protection (as in VI) in acidic medium, it seemed worthwhile to investigate a synthetic procedure based on the use of diphenylmethyl 4,5-0-isopropylidenequinate (II), a compound without any protection on the 1-hydroxyl-function. This approach looked promising, because in I1 a marked difference towards acid chlorides between the sterically hindered, axial tert. alcohol group on C-1 and the equatorial sec. alcohol group on C-3 may be expected (see e.g. ( 7 -1 0 ) ) .The results obtained confirm the validity of this supposition. The procedure, followed for the synthesis of the title compounds VIII, XI and XI1 is depicted in the scheme.-663 -

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Zusammenfassende �bersichtsberichte �ber Hydroxy-zimts�uren und ihre Bedeutung in Lebensmitteln

Cited by 26 publications

References 116 publications

Determination of 2,3,6-trichlorobenzoic acid residues in grain and straw with electron-capture gas chromatography

Determination of 2,3,6-trichlorobenzoic acid residues in grain and straw with electron-capture gas chromatography

N‐acylamino acids and peptides I. The synthesis of N‐feruloylamino acids

Synthesis of 3‐0‐o.coumaryl‐, 4‐0‐o.coumaryl‐and 3‐0‐ferulyl‐d‐(‐)‐quinic acid. Improved synthesis of 3‐0‐sinapyl‐d‐(‐)‐quinic acid

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