Thienyl analogues of acyclic monoterpene alcohols and their biological activity

Bonikowski, Radosław; Sikora, Magdalena; Kula, Józef; Kunicka, A.

doi:10.1002/jsfa.3696

Cited by 11 publications

(17 citation statements)

References 26 publications

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“…According to the protocol described earlier, six experienced panelists evaluated the scents of the new compounds and participated in their odour threshold determination. Odour tenacity was discerned in a manner described elsewhere …”

Section: Methodsmentioning

confidence: 99%

“…Weyerstahl synthesized a number of thiophene derivatives: analogues of rose furan and perillene, which are the essential components of rose oil . A series of analogues of acyclic monoterpene alcohols in which the isobutenyl moiety was replaced by a thiophene or methylthiophene group was also synthesized and olfactorily characterized . Turin patented a few thiophene derivatives, termed cyclamenaldehyde analogues, in which the benzene ring was replaced by the thiophene core .…”

Section: Introductionmentioning

confidence: 99%

“…In general, the odour of the thiophenes is comparable with that of the corresponding furans, and the smell of thienyl analogues of acyclic monoterpenes are reminiscent of the parent terpenes. The tenacity of the odour of sulfur derivatives is many times longer, however, mainly as a result of lower vapour pressure . It is worth adding that thiophene compounds exhibit many other biological activities: e.g.…”

Section: Introductionmentioning

confidence: 99%

“…During the commercial production of 3‐methyl‐5‐(3‐methylthiophen‐2‐yl)pent‐1‐en‐3‐ol, a large quantity of 4‐[3‐methyl‐5‐(3‐oxobutyl)thiophen‐2‐yl]butan‐2‐one ( 1 ) is produced as a by‐product during the 3‐methylthiophene alkylation with methylvinylketone . This inspired us to continue our further research on the synthesis of volatile thiophene derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of thiophene derivatives with long‐lasting citrusy type odour

Kost

Matysiak

Kula

et al. 2018

Flavour & Fragrance J

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Starting from 3‐methylthiophene, 11 new sensory‐active thiophene derivatives were synthesized. Among them, 3‐(5‐butyl‐3‐methylthiophen‐2‐yl)‐1‐methylpropyl acetate (3), 2,5‐dibutyl‐3‐methylthiophene, and 1‐methyl‐3‐(3‐methylthiophen‐2‐yl)propyl acetate (12) were characterized by long‐lasting citrus scents. The individual enantiomers of esters 3 and 12, which have been characterized in terms of fragrance, were also obtained.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of thiophene derivatives with long‐lasting citrusy type odour

Kost

Matysiak

Kula

et al. 2018

Flavour & Fragrance J

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“…In our previous studies [15][16][17], we described the synthesis and mainly the odour activity of the analogues of acyclic terpenoids where isobutenyl moiety was replaced by a furan or thiophene ring.…”

Section: Figurementioning

confidence: 99%

Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity

et al. 2015

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By implementing a common and industrially used method, 30 compounds which are structurally related to geranyl acetone, nerolidol, farnesal, farnesol and farnesyl acetate were obtained. Their antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, Escherichia coli, Klebsiella pneumoniae and Acinetobacter baumannii bacteria was investigated. Pharmacophore models were proposed based on the obtained results and 3D QSAR modelling. Cytotoxic effects against mainly human immortalised and normal cell lines of different origin (malignant melanoma MeWo, colorectal adenocarcinoma HT29, promyelocytic leukemia HL60, gingival fibroblasts HFIG, skin keratinocytes HaCaT and rat small intestine epithelium IEC6) were examined. The odour descriptions of newly synthesised compounds are given.

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Synthesis of (R)‐ and (S)‐Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity

Matysiak

Zabielska

Kula

et al. 2018

J Americ Oil Chem Soc

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A series of fatty acid amides derived from (R)‐ and (S)‐ricinoleic acid and 4 cyclic and acyclic amines were synthesized in a proecological solvent‐free process with yields ranging from 43 to 88%. All S‐configured compounds and both enantiomers of amide with 2‐amino‐2‐methyl‐1‐propanol were obtained and studied in terms of biological activity for the first time. The evaluation of antimicrobial activity of (R)‐ and (S)‐ricinoleic acid derivatives against 13 different microorganisms representing Gram‐negative and Gram‐positive bacteria, yeast, and molds showed significant inhibitory activity against Gram‐positive bacteria, especially Micrococcus luteus and Bacillus subtilis, and against selected molds. Ethanolamine‐ and pyrrolidine‐derived amides showed the most promising antibacterial and antimold potential. Derivatives from ricinoleic acid and pyrrolidine were the most active against both selected molds, Aspergillus brasiliensis and Penicillium expansum. Moreover, the R‐configured analog was the most potent against B. subtilis. The amides of ricinoleic acid with ethanolamine exhibited significant potential to Staphylococcus aureus, which distinguished them from the rest of tested derivatives to which this bacterium was very resistant.

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Thienyl analogues of acyclic monoterpene alcohols and their biological activity

Abstract: BACKGROUND: Thienyl analogues of linalool, geraniol, nerol and citronellol were synthesised and their sensory and antimicrobial activities were investigated.

Cited by 11 publications

References 26 publications

Synthesis of thiophene derivatives with long‐lasting citrusy type odour

Synthesis of thiophene derivatives with long‐lasting citrusy type odour

Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity

Synthesis of (R)‐ and (S)‐Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity

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