Studies on analogs of DAMASCENOLIDETM: Part 4. Synthesis and odor evaluation of sulfur-containing analogs of DAMASCENOLIDETM

2021 ◽  
Author(s):  
Yamato Miyazawa ◽  
Kenji Kawaguchi ◽  
Ryo Katsuta ◽  
Tomoo Nukada ◽  
Ken Ishigami
Keyword(s):  
Sulfur Atom ◽  
Development Project ◽  
Aroma Compounds ◽  
Odor Intensity ◽  
Aroma Compound ◽  
Odor Evaluation ◽  
Damask Rose ◽  
Sulfur Containing ◽  
Sulfur Containing Compounds

ABSTRACT DAMASCENOLIDETM [1, 4-(4-methylpent-3-en-1-yl)furan-2(5H)-one], which is isolated from damask rose, is a useful aroma compound with a citrus-like odor. We have previously reported on the synthesis and odor properties of 34 analogs of 1 as part of our new aroma compound development project. In order to develop better aroma compounds and to gather more information on structure-odor relationships, six novel sulfur-containing analogs of 1 were synthesized. Odor evaluation revealed that their odors differed significantly from those of the corresponding sulfur-free compounds. The introduction of a sulfur atom does not necessarily result in a sulfur-like odor. In particular, the 2(5H)-thiophenone analogs gave waxy, oily and lactone-like odors that are uncharacteristic of sulfur-containing compounds. In many synthesized analogs, the introduction of a sulfur atom led to an increase in odor intensity, as expected.

Synthesis of cyclopentane analogs of (2′- and 3′-deoxy-erythro-pentofuranosyl and ribofuranosyl)-2-thiouracil nucleosides

1986 ◽  
Vol 64 (8) ◽  
pp. 1620-1629 ◽  
Author(s):  
Lucjan J.J. Hronowski ◽  
Walter A. Szarek
Keyword(s):  
Sulfur Atom ◽  
Nmr Spectra ◽  
Aqueous Ammonia ◽  
Synthetic Route ◽  
Nmr Spectrum ◽  
H Nmr ◽  
Synthetic Intermediates ◽  
Derivatives Of ◽  
Sulfur Containing ◽  
Sulfur Containing Compounds

Three new carbocyclic analogs of nucleosides having the 2-thiouracil base have been synthesized. The cyclopentyl groups in these nucleosides are (±)-{(1β,3α,4β)-3-hydroxy-4-(hydroxyrnethyl)cyclopentyl} (see 31), (±)-{(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl} (see 32), and (±)-{(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl} (see 33). The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides. In addition a modified and shortened synthetic route is described for the synthesis of (±)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19). The 1H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed. It is shown that each nucleoside has a characteristically unique 1H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower fields than those in the corresponding oxygen-containing compounds. The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.

Molecular Reconstruction of Hydrocarbons and Sulfur-Containing Compounds in Atmospheric and Vacuum Gas Oils

2021 ◽  
Author(s):  
Aleksandar Bojkovic ◽  
Thomas Dijkmans ◽  
Hang Dao Thi ◽  
Marko Djokic ◽  
Kevin M. Van Geem
Keyword(s):  
Sulfur Containing ◽  
Sulfur Containing Compounds

scholarly journals Salt and Aroma Compound Distributions Influence Flavour Release and Temporal Perception While Eating Hot-Served Flans

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1300
Author(s):  
Marion Emorine ◽  
Chantal Septier ◽  
Christophe Martin ◽  
Sylvie Cordelle ◽  
Etienne Sémon ◽  
...  
Keyword(s):  
Salt Content ◽  
Optimal Solution ◽  
Proton Transfer Reaction ◽  
Aroma Compounds ◽  
Aroma Compound ◽  
Taste Intensity ◽  
Heterogeneous Distribution ◽  
Flavour Compounds ◽  
Flight Mass Spectrometry

To counteract the negative effect of salt overconsumption on health, strategies have been developed to reduce the salt content in food products. Among them, two promising strategies based on odour-induced saltiness enhancement and the heterogeneous distribution of flavour compounds were combined and assessed in four-layer cream-based snacks. To investigate the relationship between saltiness enhancement, temporal release and perception of flavour compounds in hot snacks with heterogeneous distribution of salt and aroma compounds, complementary techniques were used: nose space PTR-Tof-MS (Proton Transfer Reaction-Time of Flight–Mass Spectrometry) to assess the release of aroma compounds in vivo, and ATI (Alternate Time-Intensity) and TDS Temporal Dominance of Sensations) to evaluate perception as a function of time. The obtained results confirmed that the strategy of concentrating salt in the outer layer of a multilayer product was the optimal solution with respect to taste intensity. Heterogeneous salt distribution decreased aroma compound release and consequently aroma intensity but in different ways according to both salt and added aroma distribution in the food matrix. The salty taste enhancement could be due to the initial strong dominance of the salty sensation at the very beginning of the eating process. The involved mechanisms rely on a combination of physico-chemical and perceptual effects which are not clear yet.

scholarly journals Effect of WC/Ni–Cr additive on changes in the composition of an atmospheric residue in the course of cracking

2019 ◽  
Vol 17 (2) ◽  
pp. 499-508 ◽  
Author(s):  
Galina S. Pevneva ◽  
Natalya G. Voronetskaya ◽  
Nikita N. Sviridenko ◽  
Anatoly K. Golovko
Keyword(s):  
Molecular Weight ◽  
Tungsten Carbide ◽  
Aromatic Hydrocarbons ◽  
Aromatic Compounds ◽  
Low Molecular Weight ◽  
Nickel Chromium ◽  
Atmospheric Residue ◽  
Sulfur Containing ◽  
Catalytic Additive ◽  
Sulfur Containing Compounds

AbstractThe paper presents the results of investigation of changes in the composition of hydrocarbons and sulfur-containing compounds of an atmospheric residue in the course of cracking in the presence of a tungsten carbide–nickel–chromium (WC/Ni–Cr) catalytic additive and without it. The cracking is carried out in an autoclave at 500 °C for 30 min. The addition of the WC/Ni–Cr additive promotes the deepening of reactions of destruction not only of resins and asphaltenes, but also high molecular weight naphthene-aromatic compounds of the atmospheric residue. It is shown that the content of low molecular weight C9–C17 n-alkanes and C9–C10 alkylbenzenes rose sharply in the products of cracking with addition of WC/Ni–Cr in comparison with those produced without the additive. Alkyl- and naphthene-substituted aromatic hydrocarbons of benzene, naphthalene, phenanthrene series, polyarenes, benzo- and dibenzothiophenes are identified.

Effect of sulfur-containing compounds on viscose ripening

1980 ◽  
Vol 11 (3) ◽  
pp. 208-210
Author(s):  
E. P. Ovchinnikova ◽  
L. S. Abramova ◽  
Z. A. Rogovin
Keyword(s):  
Sulfur Containing ◽  
Sulfur Containing Compounds

Control of the Nephrotoxicity of Cisplatin by Clinically Used Sulfur-Containing Compounds

1992 ◽  
Vol 18 (2) ◽  
pp. 181-188
Author(s):  
MARK M. JONES ◽  
MARK A. BASINGER ◽  
MYRON A. HOLSCHER
Keyword(s):  
Sulfur Containing ◽  
Sulfur Containing Compounds
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