1970
DOI: 10.1002/cber.19701031204
|View full text |Cite
|
Sign up to set email alerts
|

Über die Inhaltsstoffe des schwarzen Pfeffers

Abstract: Aus Piper niRrlrrn wcrden drei neue Nebenalkaloide isoliert. Das ,,Chavicin", das bisher als Geschmackstragcr dcs Pfeffers angegeben wurde, ist kein cixcis-Piperin, sondern ein Gemisch aus Piperin und vcrschiedenen Nebenalkaloiden; cis.ci,s-Piperin kann im Pfeffer nicht nachgewiesen werdcn. Samtliche cis-trans-isomeren Piperinsawen und ihre Piperidide werden synthetisiert. lhre Eigenschaften beweisen ebenfalls, da8 das ,,Chavicin" der alteren Literatur kein lsomercs des Piperins gewesen sein kann. I>er scharfe… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

2
23
1
2

Year Published

1971
1971
2013
2013

Publication Types

Select...
6
2

Relationship

0
8

Authors

Journals

citations
Cited by 65 publications
(28 citation statements)
references
References 15 publications
2
23
1
2
Order By: Relevance
“…It was presumed from the UV data as shown in Table I that a 2E,4E configuration in a diene system would be present in compound 4 (piperine, ~max 340 nm), a 2Z,4Z configuration in I (chavicine, Imax 3 18 nm), a 2E,4Z or 2Z,4E configuration in 2 and 3 (isochavicine or isopiperine, Imax 329 and 335 nm). The UV data were in agreement with those of synthesized piperine isomers reported in the literature (Grewe et al, 1970;Yamamoto et al, 1974;De Cleyn & Verzele, 1975a,b). The detailed structural elucidation for 1, 2, 3 and 4 was determined on the basis of NMR experiments.…”
Section: Methodssupporting
confidence: 90%
See 1 more Smart Citation
“…It was presumed from the UV data as shown in Table I that a 2E,4E configuration in a diene system would be present in compound 4 (piperine, ~max 340 nm), a 2Z,4Z configuration in I (chavicine, Imax 3 18 nm), a 2E,4Z or 2Z,4E configuration in 2 and 3 (isochavicine or isopiperine, Imax 329 and 335 nm). The UV data were in agreement with those of synthesized piperine isomers reported in the literature (Grewe et al, 1970;Yamamoto et al, 1974;De Cleyn & Verzele, 1975a,b). The detailed structural elucidation for 1, 2, 3 and 4 was determined on the basis of NMR experiments.…”
Section: Methodssupporting
confidence: 90%
“…The detailed structural elucidation for 1, 2, 3 and 4 was determined on the basis of NMR experiments. IH-lH NOE and C/H COSY were measured, in order to recognize the reported IH assignments (Grewe et al, 1970;Wenkert et al, 1971;Yamamoto et al, 1974;De Cleyn & Verzele, 1975a, b;Tsuboi et al, 1984) and to assign the 13C signals in the spectra 125. 2, 3 and 4.…”
Section: Methodsmentioning
confidence: 99%
“…The 2,4-dienoate was prepared by condensation of the aldehyde with the phosphonate in the presence of sodium methoxide, whose configurations were predominantly trans at C-2 and exclusively trans at C-4. The protecting group of the 2,4-dienoate was removed by p-toluenesulfonic acid or tosic acid (p-TsOH) in MeOH to give (2E,4E)-methyl 10-hydroxy-2,4-decadienoate, which was oxidized with pyridinium chlorochromate to (2E,4E)-methyl 10-oxo-2,4-decadienoate.The piperonyl moiety, piperonyl alcohol, was brominated with phosphorus tribromide (PBr 3 ) to give piperonyl bromide in quantitative yield, which was converted to 3,4-methylenedioxybenzyl-triphenylphosphonium bromide(93% yield) with triphenylphosphine according to the method of Grewe et al (1970). The phosphonium bromide in benzene was converted with an equimolar amount of n-butyllithium (n-BuLi) in n-hexane solution to the Wittig reagent, which was coupled in situ with an equimolar amount of (2E,4E)-methyl 10-oxo-2,4-decadienoate to give the condensation product in 70% yield.…”
Section: Total Synthesis Of Pipercidementioning
confidence: 99%
“…Treatment of this product with oxalyl chloride and acylation of 1,2-methylenedioxybenzene in the presence of stannic chloride gave the Friedel-Crafts acylation product, methyl ω-piperonoyloctanoate. NaBH 4 reduction of the keto-ester, followed by dehydration and hydrolysis gave piperolein B acid which was known (Grewe et al, 1970). LiAlH 4 reduction of the acid followed by CrO 3 /Py oxidation gave the corresponding aldehyde which was subjected to Wittig reaction with γ-triphenylphosphorane methyl crotononate to give 20% all-trans methyl guineensate.…”
Section: Total Synthesis Of Guineensinementioning
confidence: 99%
“…On the other hand, synthesis of guineensine 5 (piperamide-B13:3(2E,4E,12E)) from P. guineense (1 1) or piperolein B (piperamide-A9: l(8E)) from P. nigr~lrn (12) dictates an aldol condensation -fragmentation involving cyclooctanone and piperonal.…”
Section: Introductionmentioning
confidence: 99%