3268-49-3 Usage
Description
3-(Methylthio)propionaldehyde is a synthetic flavoring agent that is a colorless to light yellow liquid with an intense meat odor. It polymerizes with age and is stable in a 50% alcohol solution. It should be stored in glass containers.
Uses
Used in Food Industry:
3-(Methylthio)propionaldehyde is used as a food flavor for making baked food, spices, soft drinks, and candy. It is used at low concentrations for meat and broth flavors for applications in meats and condiments at 3 ppm and in baked goods and beverages at 0.5 ppm.
Used in Organic Synthesis:
3-(Methylthio)propionaldehyde is also used as an intermediate in organic synthesis as solvents as well as reagents. It has wide applications in the synthesis of specific compound classes, including agricultural chemicals, property-enhancing additives, pharmacological drugs, chemical-resistant polymers, detergents, and rubber antioxidants.
Taste and Aroma Characteristics:
3-(Methylthio)propionaldehyde has taste characteristics at 5 ppb to 5 ppm, including potato, musty, tomato, mold-ripened cheeses, onion, beefy brothy, egg, seafood, and vegetative nuances. Its aroma characteristics at 0.1% include vegetable oil, creamy tomato, potato skin and French fry, yeasty, bready, and Limburger cheese with a savory meaty brothy nuance.
Occurrence:
3-(Methylthio)propionaldehyde is reported to be found in various natural sources such as potato, potato chips, asparagus, tomato, tomato paste, wheat and rye bread, many cheeses, boiled egg, meats, hop oil, beer, malt whiskey, cocoa, coffee, roasted filberts and peanuts, popcorn, baked potato, cooked chicken, oatmeal, passion fruit, beans, mushroom, macadamia nut, tamarind, parsnip root, jackfruit, pumpkin, sweet corn, dried bonito, krill, shrimps, crayfish, and scallops.
General Description:
3-(Methylthio)propionaldehyde is a colorless to amber liquid with an extremely foul and persistent odor. It is slightly soluble in water and denser than water. Contact may slightly irritate skin, eyes, and mucous membranes. It is moderately toxic and used as a food additive.
Preparation
By transamination and decarboxylation of various amino acids; by oxidation of the alcohol
Synthesis Reference(s)
Journal of the American Chemical Society, 70, p. 1450, 1948 DOI: 10.1021/ja01184a044
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Organosulfides, such as 3-(Methylthio)propionaldehyde, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.
Health Hazard
Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
Taste at 0.5-1ppm
Safety Profile
Moderately toxic by
ingestion. When heated to decomposition it
emits toxic vapors of SOx.
Check Digit Verification of cas no
The CAS Registry Mumber 3268-49-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,6 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3268-49:
(6*3)+(5*2)+(4*6)+(3*8)+(2*4)+(1*9)=93
93 % 10 = 3
So 3268-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H8OS/c1-4(3-5)6-2/h3-4H,1-2H3
3268-49-3Relevant articles and documents
Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model
Cui, Heping,Deng, Shibin,Hayat, Khizar,Ho, Chi-Tang,Zhai, Yun,Zhang, Qiang,Zhang, Xiaoming
, (2022/03/07)
The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.
Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis
Wei, Zheyu,Ru, Shi,Zhao, Qixin,Yu, Han,Zhang, Gang,Wei, Yongge
supporting information, p. 4069 - 4075 (2019/08/07)
The oxidation of alcohols to aldehydes or ketones is a highly relevant conversion for the pharmaceutical and fine-chemical industries, and for biomass conversion, and is commonly performed using stoichiometric amounts of highly hazardous oxidants. The aerobic oxidation of alcohols with transition metal complex catalysts previously required complicated organic ligands and/or nitroxyl radicals as co-catalysts. Herein, we report an efficient and eco-friendly method to promote the aerobic oxidation of alcohols using an inorganic-ligand supported copper catalyst 1, (NH4)4[CuMo6O18(OH)6], with O2 (1 atm) as the sole oxidant. Catalyst 1 is synthesized directly from cheap and commonly available (NH4)6Mo7O24·4H2O and CuSO4, which consists of a pure inorganic framework built from a central CuII core supported by six MoVIO6 inorganic scaffolds. The copper catalyst 1 exhibits excellent selectivity and activity towards a wide range of substrates in the catalytic oxidation of alcohols, and can avoid the use of toxic oxidants, nitroxyl radicals, and potentially air/moisture sensitive and complicated organic ligands that are not commercially available. Owing to its robust inorganic framework, catalyst 1 shows good stability and reusability, and the catalytic oxidation of alcohols with catalyst 1 could be readily scaled up to gram scale with little loss of catalytic activity, demonstrating great potential of the inorganic-ligand supported Cu catalysts in catalytic chemical transformations.
Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst
Zhang, Mengqi,Zhai, Yongyan,Ru, Shi,Zang, Dejin,Han, Sheng,Yu, Han,Wei, Yongge
supporting information, p. 10164 - 10167 (2018/09/13)
Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.