- Key Odor-Active Compounds in Raw Green and Red Toona sinensis (A. Juss.) Roem. And Their Changes during Blanching
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Application of aroma extract dilution analysis and headspace aroma dilution analysis revealed 51 odorants in raw green Toona sinensis and 54 odorants in raw red T. sinensis in the flavor dilution factor range of 8-4096. (E,E)-2,4-Decadienal, nonanal, 2,3,5-trimethylpyrazine, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, 2-methoxyphenol, and 4-ethylphenol were first identified as key odorants of T. sinensis. Clear differences between green and red T. sinensis in aroma profiles, flavor dilution factors, quantitative data, and odor activity values verified that (E,E)-, (E,Z)-, and (Z,Z)-di-1-propenyl disulfide, (E,E)-, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, cis- and trans-2-mercapto-3,4-dimethyl-2,3-dihydrothiophene, and dimethyl sulfide caused the distinct sulfury odor note of each variety. Further, hexanal, (E)-2-hexenal, (E)-2-hexen-1-ol, and (E,Z)-2,6-nonadienal led to the green odor note in green T. sinensis, while 2-methoxyphenol and 4-ethylphenol contributed to the intense phenolic aroma note in red T. sinensis. Quantitation experiments and triangle tests in blanched T. sinensis verified that the quick loss of the abovementioned sulfur-containing compounds, aldehydes, the alcohol (E)-2-hexen-1-ol, and phenols was responsible for the changes in the overall aroma profile during blanching.
- Granvogl, Michael,Zhai, Xiaoting
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- Selectivity of diallyl trisulfides (DATS) in reducing HAuCl4 to produce gold nanoparticles: a detailed investigation
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The bulbous root garlic (Allium sativum) with a strong taste and pungent odor is used widely in culinary preparations and folk medicine. Silver and gold nanoparticles (NPs) synthesized using this ingredient have also shown medicinal and therapeutic potency. Garlic contains organosulfur compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS). These compounds are of crucial significance as anticancer drugs. Reported here is a synthesis of a series of DATS with varying substituents and plausible application as capping as well as reducing agent to synthesize gold nanoparticles (TS-GNPs). In the process, it was discovered that among the selected DATs, only 1,3-di(but-1-ene)trisulfane could serve the purpose because of structural reasons. The reason for this intriguing selectivity has been investigated in detail using the experimental findings and theoretical calculations of the frontier molecular orbitals (FMO). Graphic abstract: Synthesis of a series of medicinally important symmetrical organic trisulfides as a structural analogue of diallyl trisulfides (DATS) in an attempt to construct organosulfur compound induced gold nanoparticles (GNPs), has been reported. Only 1,3-Di(but-1-ene)trisulfane in the lot is capable of reducing the chloroauric acid to synthesize the protected GNPs.[Figure not available: see fulltext.].
- Chatterjee, Arunavo,Mandal, Niladri Sekhar,Purkayastha, Pradipta
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- Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles
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Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.
- Bhattacherjee, Debojit,Sufian, Abu,Mahato, Sulendar K.,Begum, Samiyara,Banerjee, Kaustav,De, Sharmistha,Srivastava, Hemant Kumar,Bhabak, Krishna P.
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supporting information
p. 13534 - 13537
(2019/11/14)
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- Substituent effects on the reactivity of benzo-1,2-dithiolan-3-one 1-oxides and their possible application to the synthesis of DNA-targeting drugs
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The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3- one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.
- Sawwan, Nahed,Brzostowska, Edyta M.,Greer, Alexander
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p. 6968 - 6971
(2007/10/03)
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- Formation of dialkyl polysulfides from vinyl ethers in the system H2S-DMSO-MOH
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The reaction of vinyl ethers with the system H2S-DMSO-MOH (30°C, 5 h) gives dialkyl polysulfides with a total yield of up to 65% instead of expected oxygen-containing thiols and sulfides. The ratio between dialkyl di-, tri-, and tetrasulfides depends on the nature of the vinyl ether and on the amount of alkali metal hydroxide in the reaction mixture. With di(propen-1-yl) ether, 4-methyl-2-ethyl-1,3-oxathiolane was also found as a by-product.
- Musorin,Sedunova,Trofimov
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p. 794 - 797
(2007/10/03)
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- Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates
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At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.
- Do, Quang Tho,Elothmani, Driss,Simonet, Jacques,Guillanton, Georges Le
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p. 273 - 281
(2007/10/03)
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- Reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: Studies related to the reaction of antitumor antibiotic leinamycin with DNA
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We have studied the reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide. The major products isolated from these reactions are the corresponding dithio carboxylic acids. In the case of 3H-1,2-benzodithiol-3-one 1-oxide, an unstable hydrodisulfide that decomposes to polysulfides under the reaction conditions is formed. A mechanism involving an unstable oxathiolanone intermediate is proposed for these reactions. We believe that these reactions may serve as useful models for some aspects of the thiol-activated DNA-cleavage chemistry of the antitumor antibiotic leinamycin, a natural product that contains a 1,2-dithiolan-3-one 1-oxide heterocycle.
- Behroozi,Kim,Gates
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p. 3964 - 3966
(2007/10/02)
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- REACTION OF SULFUR DIOXIDE WITH THIOLS CATALYZED BY BORON TRIFLUORIDE ETHERATE. EVIDENCE FOR A POSSIBLE INTERVENTION OF DITHIOSULFITE AS A REACTION INTERMEDIATE.
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The reaction of sulfur dioxide (SO//2) with 1-propanethiol (NPT), 2-propanethiol (IPT), or 2-methyl-2-propanethiol (TBT) catalyzed by boron trifluoride ethrate (BF//3OEt//2) was investigated. The ratios of dialkyl trisulfide to dialkyl disulfide obtained (RSSSR/RSSR) at an early stage of the reaction were larger than 1 for the reaction of TBT and less than 1 for the reaction of NPT or IPT. The reaction of dithiosulfites with BF//3OEt//2 in the presence or absence of thiol was investigated. From a consideration of the similarity of the composition of the sulfides formed in the reaction of dithiosulfites with BF//3OEt//2 to those in the reaction of SO//2 witn thiol in the presence of BF//3OEt//2, the possibility of the intervention of dithiosulfite as a reaction intermediate in the reaction of SO//2 with thiol is discussed.
- Akiyama
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p. 2657 - 2660
(2007/10/02)
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- Desulfurization of Organic Trisulfides by Tris(dialkylamino)phosphines. Mechanistic Aspects
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Tris(dialkylamino)phosphines effect a rapid desulfurization of trisulfides to disulfides under mild conditions.The reaction mechanism involves a bimolecular process, proceeding by the rate-determining formation of a phosphonium salt intermediate.The central sulfur atom of a diaryl trisulfide is removed in the process, while a dialkyl trisulfide loses a terminal sulfur atom to the aminophosphine.
- Harpp, David N.,Ash, David K.,Smith, Roger A.
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p. 5155 - 5160
(2007/10/02)
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- A NEW SYNTHESIS OF ORGANIC TRISULFIDES
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Thiols react with diimidazolylsulfide under mild conditions to give simmetrical trisulfides in good yield and high purity.
- Banerji, Asoke,Kalena, Govind P.
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p. 3003 - 3004
(2007/10/02)
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