164524-93-0

Basic information

• Product Name: Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- (9CI)
• Synonyms: Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- (9CI);ethanone,1-(3,4-dihydro-2H-1,4-thiazin-5-yl)-;1-(3,4-Dihydro-2H-1,4-thiazin-5-yl)ethanone;5- acetyl-2,3-dihydro-1,4-thiazine
• CAS NO: 164524-93-0
• Molecular Formula: C6H9NOS
• Molecular Weight: 143.20676
• Product Categories: ACETYLGROUP
• Mol File: 164524-93-0.mol

Chemical Properties

• Boiling Point: 289℃
• Flash Point: 129℃
• Appearance: /
• Density: 1.150
• Vapor Pressure: 0.0022mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: 2-8°C
• PKA: 3.29±0.40(Predicted)
• CAS DataBase Reference: Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- (9CI)(164524-93-0)
• EPA Substance Registry System: Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- (9CI)(164524-93-0)

Safety Data

• Hazardous Substances Data: 164524-93-0(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in various food categories for its nutty, cooked, brown, and roasted aroma. It is used within specific usage levels (ppm) to enhance the taste and aroma of different food products.
Used in Seasonings and Flavors:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavor enhancer in seasonings and flavors, with a usage range of 50 to 1000 ppm, to provide a rich and complex aroma to the final product.
Used in Alcoholic Beverages:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in alcoholic beverages, with a usual usage level of 2 ppm and a maximum level of 10 ppm, to add depth and complexity to the taste profile.
Used in Baked Goods:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in baked goods, with a usual usage level of 5 ppm and a maximum level of 20 ppm, to impart a unique aroma and taste to the final product.
Used in Breakfast Cereal:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in breakfast cereal, with a usual usage level of 5 ppm and a maximum level of 20 ppm, to enhance the taste and aroma of the cereal.
Used in Cheese:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in cheese, with a usual usage level of 1 ppm and a maximum level of 5 ppm, to add a distinct flavor note to the cheese.
Used in Confections and Frostings:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in confections and frostings, with a usual usage level of 2 ppm and a maximum level of 10 ppm, to provide a unique aroma and taste to the sweet treats.
Used in Frozen Dairy:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in frozen dairy products, with a usual usage level of 1 ppm and a maximum level of 5 ppm, to enhance the taste and aroma of the frozen desserts.
Used in Hard Candy:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in hard candy, with a usual usage level of 2 ppm and a maximum level of 10 ppm, to add a distinctive flavor to the candy.
Used in Imitation Dairy:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in imitation dairy products, with a usual usage level of 2 ppm and a maximum level of 10 ppm, to provide a creamy and rich taste to the product.
Used in Instant Coffee and Tea:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in instant coffee and tea, with a usual usage level of 2 ppm and a maximum level of 10 ppm, to enhance the aroma and taste of the instant beverages.
Used in Meat Products:
Ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)(9CI) is used as a flavoring agent in meat products, with a usual usage level of 1 ppm and a maximum level of 5 ppm,

Identification

▼▲ CAS.No.:? 101417-25-8 164524-93-0? FL.No.:? 15.114 FEMA.No.:? 4296 NAS.No.:? n/a? CoE.No.:? n/a? EINECS.No.? n/a? JECFA.No.:? 1766

Regulatory Status

CoE: n/a FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2007).

Natural occurrence

Reported found in popcorn.

InChI:InChI=1/C6H9NOS/c1-5(8)6-4-9-3-2-7-6/h4,7H,2-3H2,1H3

Upstream product

• 69924-69-2 1-bromo-3,3-dimethoxy-butan-2-one 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 431-03-8 dimethylglyoxal 
• 60-23-1 Cysteamine 
• 207795-30-0 [2-(3,3-Dimethoxy-2-oxo-butylsulfanyl)-ethyl]-carbamic acid tert-butyl ester 
• 52-90-4 L-Cysteine 

Relevant articles and documents

Mechanistic Studies on the Formation of Thiazolidine and Structurally Related Thiazines in a Cysteamine/2,3-Butanedione Model System

Phosphate was found to dramatically enhance the formation of 2-methyl-2-acetylthiazolidine from a cysteamine/2,3-butanedione model system. In addition to the major component, 2-methyl-2-acetylthiazolidine, significant amounts of two structurally closely related compounds, 2-acetyl-2,3,5,6-tetrahydro-1,4-thiazine and 5-acetyl-2,3-dihydro-1,4-thiazine, were characterized by using GC/MS (CI and EI). There was an oxidative transformation of 2-acetyl-2,3,5,6-tetrahydro-1,4-thiazine to 5-acetyl-2,3-dihydro-1,4-thiazine in the presence of azodicarbonamide. A formation mechanism for 2-methyl-2-acetylthiazolidine and structurally related 2-acetyl-2,3,5,6-tetrahydro-1,4-thiazine and 5-acetyl-2,3-dihydro-1,4-thiazine is proposed.

Evaluation of the Key Odorants in a Thermally Treated Solution of Ribose and Cysteine by Aroma Extract Dilution Techniques

Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 deg C; 20 min) of cysteine/ribose led to the identification of 2-furfurylthiol, 3-mercapto-2-pentanone, 2-methyl-3-furanthiol, 5-acetyl-2,3-dihydro-1,4-thiazine, 3-mercapto-2-butanone, and bis(2-methyl-3-furyl) disulfide showing the highest flavor dilution factors among the 29 odor-active volatiles.HRGC/olfactometry of decreasing headspace volumes established especially 2-furfurylthiol and 2-methyl-3-furanthiol as important odorants and revealed 2-thenyl mercaptan and ethyl mercaptan as further key contributors to the overall roasty, meatlike, sulfury odor of the model mixture. 5-acetyl-2,3-dihydro-1,4-thiazine, identified for the first time among the volatiles of Maillard model reactions or foods, exhibited an intense roasty, popcorn-like odor at the low odor threshold of 0.06 ng/L of air, which was of the same order of magnitude as those reported in the literature for the roasty-smelling odorants 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline.Keywords: Aroma extract dilution analysis; nonenzymatic browning; Maillard reaction; ribose; cysteine; flavor; 5-acetyl-2,3-dihydro-1,4-thiazine

Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant

Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2-mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.

New short and general synthesis of three key Maillard flavour compounds: 2-Acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine

A new general synthetic route towards three key Maillard flavour compounds, namely 2-acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine, was developed. The key step in the process is the methylenation reaction of azaheterocyclic carboxylic esters by means of dimethyltitanocene, giving rise to intermediate vinyl ethers which can be considered as excellent and stable precursors for the title compounds, as a simple acidic treatment of these precursors suffices to release the characteristic Maillard flavours.

New short and general synthesis of three key Maillard flavour compounds: 2-Acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine

A new general synthetic route towards three key Maillard flavour compounds, namely 2-acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine, was developed. The key step in the process is the methylenation reaction of azaheterocyclic carboxylic esters by means of dimethyltitanocene, giving rise to intermediate vinyl ethers which can be considered as excellent and stable precursors for the title compounds, as a simple acidic treatment of these precursors suffices to release the characteristic Maillard flavours.

Determination of the Chemical Structure of the Intense Roasty, Popcorn-like Odorant 5-Acetyl-2,3-dihydro-1,4-thiazine

The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments.Thus, the odorant was identified as 5-acetyl-2,3-dihydro-1,4-thiazine (ADT).A sensory study including 5-propionyl-(PDT) and 5-butanoyl-2,3-dihydro-1,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcorn-like odors.However, the odor threshold of the BDT was by a factor of 50 000 higher than those ADT and PDT (0.06 and 0.1 ng/L of air, respectively).Keywords: 5-Acetyl-2,3-dihydro-1,4-thiazine; 5-propionyl-2,3-dihydro-1,4-thiazine; 5-butanoyl-2,3-dihydro-1,4-thiazine; odor threshold; synthesis; cysteamine; 2,3-butanedione