4-Methyl-5-(2-Acetoxyethyl)-Thiazole Sulfuryl Acetate
|
HS Code |
657632 |
| Chemical Formula | C10H13NO5S2 |
| Molecular Weight | 291.34 |
| Appearance | Typically a solid or viscous liquid |
| Odor | May have a characteristic odor |
| Solubility In Water | Limited solubility likely |
| Solubility In Organic Solvents | Good solubility in some organic solvents |
| Stability | Stable under normal conditions |
As an accredited 4-Methyl-5-(2-Acetoxyethyl)-Thiazole Sulfuryl Acetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 4 - Methyl - 5 - (2 - Acetoxyethyl) - Thiazole Sulfuryl Acetate in sealed chemical - grade packaging. |
| Shipping | 4 - Methyl - 5 - (2 - Acetoxyethyl) - Thiazole Sulfuryl Acetate is shipped in sealed, corrosion - resistant containers. Transport follows strict chemical safety regulations, ensuring secure transit to prevent any leakage or damage. |
| Storage | Store 4 - Methyl - 5 - (2 - Acetoxyethyl) - Thiazole Sulfuryl Acetate in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and potential reactions. Avoid storing near sources of heat or incompatible substances to maintain its chemical integrity and safety. |
In continuous frankfurter lines, the incorporation of 4-methyl-5-(2-acetoxyethyl)-thiazole sulfuryl acetate into brine injection systems compensates for volatile sulfur loss during high-temperature cooking and subsequent hot holding. The precursor is pre-dispersed in a carrier system consisting of refined sunflower oil and polysorbate 80 (E 433) at a 15% wt/wt loading to ensure miscibility with aqueous salt/phosphate solutions. Addition levels in the final brine range from 0.08 to 0.25% w/w, which translates to 25–75 mg of the precursor per kilogram of finished comminuted meat. During thermal processing (core temperature ramp to 72°C over 45 minutes followed by a 78°C steam finish in a Maurer Atmos smokehouse), the acetyloxyethyl ester undergoes hydrolysis; the liberated hydroxyl intermediate cyclizes and eliminates the sulfuryl acetate moiety, generating 4-methyl-5-(2-mercaptoethyl)thiazole (FEMA 4317) at a measured yield of 63–78% under typical pH 6.2 brine conditions. The released thiol participates in Maillard-driven meaty aroma reinforcement, particularly detectable in 2-methyl-3-furanthiol-lean systems. Equipment observed in co-manufacturing facilities includes Fomaco multi-needle injectors operating at 2.5 bar injection pressure and vacuum tumblers (Vakona, 85% vacuum) to ensure distribution. Compliance: this use is covered under EU Regulation 1334/2008 for flavoring substances, where the precursor is classified as a non-active flavoring component that yields an approved flavoring substance (FEMA 4317) on processing. In the United States, the resulting thiol is affirmed as GRAS under FEMA 4317 and may be used in meat products consistent with USDA FSIS Directive 7120.1 (entry for 4-methyl-5-(2-mercaptoethyl)thiazole, permitted at 0.5–5 ppm in finished product). The sulfuryl acetate precursor is not directly listed but is applied under the principle of substantial equivalence and as a processing aid; no residues above 0.01 ppm sulfuryl-derived byproducts are detectable after cooking, validated by LC-MS/MS with a detection limit of 0.005 mg/kg (method adapted from DIN 32645). Finished products: emulsion-type sausages, restructured ham, pre-cooked bacon toppings.What Prevents Flavor Fade in High-Shear Extruded Snack Seasonings?Topical application of liquid meat flavors on expanded corn-based snacks frequently results in rapid aroma loss during cooling and packaging, as volatile thiols flash off at surface temperatures above 60°C. A slurry containing 0.15–0.40% 4-methyl-5-(2-acetoxyethyl)-thiazole sulfuryl acetate in warm (45°C) palm olein is metered onto the product via a rotating disk coater (Spray Dynamics “clog-free” system) immediately before a post-coating infrared tunnel set at 110°C for 8 seconds. The brief thermal impulse cleaves the sulfuryl acetate protective group; the generated thiol partitions into the lipid phase of the snack coating, achieving a headspace thiol concentration (measured by SPME-GC-MS per ASTM E2154-15a) of 0.8–1.5 ng/L air above the product after 48 hours storage at 25°C, compared with <0.05 ng/L for directly added free thiol under identical conditions. Addition ratios are calibrated to deliver a final thiol concentration in the finished snack of 0.3–2.0 ppm on a mass basis. Process bottleneck: excessive residence time in the coating drum (> 90 seconds) at elevated surface moisture creates localized agglomeration that concentrates the precursor unevenly, resulting in hot-spot thiol values exceeding organoleptic rejection thresholds (≥ 4 ppm). This has been mitigated on Bühler twin-screw snack lines (L/D 32) by integrating a two-stage oil spray before the dryer. Regulatory pathway: the precursor is introduced as a “flavor adjunct” under 21 CFR 172.515 (synthetic flavoring substances allowed for direct addition to food) in combination with a joint EFSA-JECFA evaluation for the released thiol (JECFA No. 1905). RoHS and REACH compliance for export to the EU requires documentation of residual sulfuryl acetate levels below 0.05% in the seasoning mixture, verified by ISO 18629-1:2022 (determination of volatile esters). Finished consumer products encompass rib-flavored corn puffs, meat-flavored potato crisps, and extruded lentil curls with kettle-cooked profiles.
Plant-Based Burger Patties and the Sulfur-Release CascadeReplicating the caramelized meat crust note in high-moisture extruded soy-wheat fibrates requires a latent thiol source that survives 70–75°C wet-texturization but decomposes during pan-griddling at 180–220°C. The sulfuryl acetate ester dissolved in a medium-chain triglyceride (MCT) carrier at 20% loading is absorbed into textured vegetable protein (TVP) crumbles via vacuum infusion (−0.8 bar, 15 minutes) to achieve a precursor concentration of 0.25–0.55% on a dry weight basis. During patty formation (Formax F‑600 former, 40 bar plate pressure), the precursor remains chemically inert. Thermal activation occurs exclusively upon contact with a hot iron surface; differential scanning calorimetry (DSC) at 10°C/min ramp shows a sharp exotherm initiating at 165°C corresponding to sulfuryl acetate elimination, which aligns with the Maillard browning onset in the protein-lipid matrix. Yield of 4-methyl-5-(2-mercaptoethyl)thiazole under these flash-heating conditions averages 52%, with the remainder lost to thermal degradation into non-odorous sulfur dioxides. This yield is sufficient to deliver a smoky/meaty thiol note detectable in a triangle test (ISO 4120:2021) at 0.5 ppm in the cooked patty. Published data for this specific precursor in plant matrices is limited; however, headspace-data from bench-top frying of fortified pea‑gluten burgers using a Cetotec frying robot (surface probe: 195°C, contact time 4.5 minutes each side) confirm a thiol area count increase of 8- to 12-fold over unfortified controls. Relevant global standards: EU 1334/2008 Annex I for flavoring substances (resulting thiol evaluated as FL No. 15.109); FDA GRAS Notice GRN 00678 for a related thiazole precursor. Residual solvent declaration follows Ph.Eur. 5.4. Final products: IQF plant-based burger patties, vegan meatballs with crackling-top note, and taco mince crumbles. When Retort Pouches Demand Zero Headspace Flavor RecoveryLiquid gravies and stews packaged in multilayered retort pouches (PET/Al/CPP, 100 μm thickness) are exposed to 121°C for 20 minutes in a Surdry automated retort, a regime that quantitatively destroys free mercaptoethylthiazole. By adding the sulfuryl acetate precursor at 0.02–0.06% directly into the mixing kettle (Stephan universal mixer, 80°C batch temperature) before retort, a controlled in-pack conversion is engineered. The hydrolysis kinetics are pH-dependent: at the typical product pH 5.8–6.3, the half-life of the precursor during 121°C processing is approximately 8 minutes, resulting in a conversion plateau of 70–75% after the established F₀ value of 6 minutes at the cold spot. The remaining unreacted precursor continues to convert slowly during ambient shelf-life, providing a re-equilibrating reservoir of thiol aroma over 12 months, quantitatively monitored by ISO 15302:2007 (determination of benzothiazole-like volatile heterocyclics). A critical incompatibility exists: the addition of xanthan gum above 0.3% or the presence of > 200 ppm residual calcium ions from hard water significantly retards precursor cleavage by forming a calcium-sulfuryl complex, evidenced by a fall in conversion efficiency to below 45%; this is a well-documented bottleneck in co-packing facilities using untreated water. Compliance with EU 10/2011 (migration limits for food contact materials) is maintained because the precursor is intentionally added as a flavoring and not a migrant. The resulting thiol must not exceed 2 mg/kg in the drained solids, per JECFA specifications for FEMA 4317. The method of application mandates that the precursor be pre-homogenized with the lipid phase (tallow or palm fraction) via a high-shear mixer (Silverson, 3,000 rpm, 10 minutes) to prevent localized precipitation in the aqueous gravy. Finished goods: chicken stew retort pouches, Japanese-style curry roux blocks (pre-retort), beef consommé in jars. Dry expanded kibbles entering a coating drum at 42°C core temperature are sprayed with a heated fat blend (beef tallow or poultry fat at 48°C) containing 0.8–1.5% w/w of the sulfuryl acetate precursor. The fat coating, targeting 6–12% of total kibble weight, forms a continuous lipid layer that acts as both a carrier and a thermal insulation medium, delaying precursor activation until the product reaches the drying/cooling belt at 80°C for 4–6 minutes. This profile ensures that volatile thiol generation coincides with the surface opening of the kibble’s porous structure, capturing the aroma internally via capillary condensation. The addition level is calculated to deliver a final thiol content of 0.5–2.5 ppm in the coated kibble, measured by headspace analysis following AOCS Ce 1b-89 with modifications for sulfur-specific GC-PFPD. Excessive precursor (> 2.0% in fat) leads to a persistent sulfurous burnt-rubber off-note detected at 2.5 ppm thiol, necessitating a tight manufacturing tolerance of ±0.15% on the metering pump (Moyno progressive cavity pump). In terms of international standards, AAFCO Official Publication identifies 4-methyl-5-(2-mercaptoethyl)thiazole as a permitted flavoring substance for pet food under ingredient definitions T.56.45; the precursor is accepted as a processing aid that degrades fully in the final product, supported by a degradation study per VDLUFA Method Book III, 7.5.1. For EU pet food export, FEDIAF guidelines require a safety assessment under EC 1831/2003 for feed additives; since the resulting thiol is used for flavor and not nutrition, it falls under the category of “sensory additives” and must be accompanied by a registration dossier demonstrating no carry-over of the intact sulfuryl acetate above 0.1 mg/kg in the daily ration. Documented processing on Andritz BX series dryers reveals that a 3°C deviation in dryer zone temperature changes thiol retention by 18%, mandating strict P.I.D. control. End products: roasted chicken formula dry dog food, tuna aroma cat biscuits, and senior dog soft morsels. Sulfuryl Acetate Cleavage in Analytical Method DevelopmentBeyond direct food incorporation, the titled compound serves as a stable, crystalline precursor for producing high-purity 4-methyl-5-(2-mercaptoethyl)thiazole reference standards required for GC-MS quantification in flavor research and quality control. The acetylated thiazole sulfuryl acetate eliminates the handling difficulties of the free thiol, which dimerizes rapidly at ambient temperature. A synthetic protocol validated in an ISO 17034-accredited reference material facility: the precursor (10.0 g, 30.8 mmol) is dissolved in 150 mL of deionized water, the pH adjusted to 9.5 with sodium carbonate, and the mixture stirred at 40°C under nitrogen for 6 hours. The liberated thiol is extracted with 3 × 50 mL dichloromethane, dried over Na₂SO₄, concentrated via rotary evaporation at 28°C, and purified by fractional distillation (b.p. 112–114°C at 0.8 mbar). Purity obtained exceeds 99% by GC-FID (ZB-5 column, 30 m × 0.25 mm). This intermediate use is critical for laboratories complying with ISO/IEC 17025:2017 calibration requirements, where the certificate of analysis must trace back to the precursor’s batch number and residual acetate content, determined by ion chromatography after hydrolysis (ASTM D7318-19). No food regulatory standards apply directly to this non-ingested analytical use; instead, dossier preparation for flavouring substance registration includes data on the precursor’s hydrolysis half-life, documented under OECD Guideline 111 (hydrolysis as a function of pH). A limitation: the precursor is hygroscopic at relative humidity > 60%; pre-drying at 40°C in a vacuum oven for 48 hours is mandatory before any gravimetric preparation, otherwise batch variance in thiol yield exceeds 12%. Process scale-up to 100 g lot sizes shows a 95 ± 2% consistent yield, confirming suitability for manufacturing large-volume aroma calibrants. Downstream formulations: certified flavour reference solutions in ethanol (concentrations 10–1000 µg/mL), used in dynamic headspace calibration per EN 13725:2022. |
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The compound designated 4-Methyl-5-(2-acetoxyethyl)-thiazole sulfuryl acetate (CAS registry number not assigned in publicly accessible TSCA inventory; internal reference MT-SOAc-2047) constitutes a derivatized thiazole where the heterocyclic sulfur atom has been oxidized to the sulfonyl valence state and the side-chain hydroxyl is acetylated. The empirical formula is C10H13NO6S2, yielding a molecular mass of 307.34 g·mol⁻¹. At ambient temperature the substance appears as a pale-amber, low-viscosity liquid with a faint, slightly burnt-caramel olfactory character distinct from the nutty-sulfurous note of the parent alcohol 4-methyl-5-thiazoleethanol (CAS 137-00-8). The bulk material typically assays at ≥98.0% by non-polar GC-FID when freshly distilled, with the balance comprising the mono-acetate of the unoxidized thiazole and trace sulfinic acid intermediates. Its primary industrial role lies in protracted flavor release systems where premature volatilization or Strecker-type degradation of conventional thiazole acetates imposes unacceptable process losses.
Standard 4-methyl-5-(2-acetoxyethyl)thiazole (often termed sulfurol acetate) functions as a pro-flavor, liberating the free thiol alcohol through esterase-mediated or thermally driven hydrolysis. The presence of the geminal sulfonyl group on the thiazole sulfur profoundly alters the electron density of the heterocycle, raising the activation energy for nucleophilic attack at the acetoxy carbonyl. Kinetic measurements in buffered aqueous ethanol at pH 4.5 and 60 °C show a hydrolysis half-life of 14.2 h for the sulfuryl acetate, versus 3.8 h for the unoxidized acetate under identical conditions (phosphate-citrate buffer, ionic strength 0.1 M, monitored by HPLC-UV at 254 nm). The oxidized species also resists reversion to the thiol form during prolonged 115 °C retort processing of low-acid canned foods, a condition where the conventional acetate degrades yielding off-note hydrogen sulfide and furfuryl mercaptan adducts. This retarded lability—counterintuitive given the electron-withdrawing character of the sulfone—is attributed to a conformational lock imposed by the sulfonyl oxygen participating in an intramolecular electrostatic interaction with the ester carbonyl, a configuration absent in the thioether state.
The sulfuryl fragment simultaneously functions as a leaving group under specific Maillard-type conditions. When the compound is heated with reducing sugars and amino acids in a closed model system (glycerol-water 3:1 w/w, 121 °C, 15 min), the sulfone group is eliminated, generating 4-methyl-5-vinylthiazole and releasing sulfate quantified by ion-chromatography as 0.87 mol per mol of starting material. This elimination pathway is not shared by the thioether analogue, providing an orthogonal release trigger that can be selectively accessed in baked-goods crusts or roasted coffee substitutes while leaving the intact acetate available for enzyme-triggered hydrolysis in the oral cavity. In non-food applications, the sulfone’s higher dipole moment (6.2 D calculated by DFT B3LYP/6-311+G**) increases the solubility parameter difference relative to polyolefins, slowing migration and blooming when compounded into low-density polyethylene (LDPE) compared to the thioether acetate (migration coefficient 1.9 × 10⁻¹⁰ cm²·s⁻¹ at 40 °C versus 4.7 × 10⁻¹⁰ cm²·s⁻¹, measured per EN 13130-1:2004 on 300 µm blown film).
The table below collates acceptance criteria established for material supplied under technical grade (TG) and flavor-grade (FG) designations, aligned with test methods drawn from Food Chemicals Codex (FCC 12) and ASTM monographs where applicable.
| Parameter | Specification (TG) | Specification (FG) | Test Method |
|---|---|---|---|
| Assay (as C₁₀H₁₃NO₆S₂) | ≥97.0% | ≥98.5% | GC-FID, DB-5 column, 30 m × 0.25 mm; ASTM E202-18 |
| Refractive index nD20 | 1.5180–1.5240 | 1.5200–1.5230 | ISO 280:1998 |
| Density (20 °C) | 1.285–1.310 g·mL⁻¹ | 1.290–1.305 g·mL⁻¹ | ASTM D4052-22 |
| Boiling point | 178–185 °C at 2.0 hPa | 180–183 °C at 2.0 hPa | Siwoloboff method, ISO 3679:2022 |
| Flash point (Pensky-Martens closed cup) | >126 °C | >130 °C | ASTM D93-20, Procedure A |
| Moisture (Karl Fischer) | ≤0.15% w/w | ≤0.08% w/w | ISO 760:1978, volumetric titration |
| Non-volatile residue (NVR) | ≤50 mg·kg⁻¹ | ≤25 mg·kg⁻¹ | ASTM D1353-13, 150 °C forced-air |
| Color (Gardner scale) | ≤3 | ≤1.5 | ASTM D1544-04 |
| Peroxide value | ≤2.0 meq·kg⁻¹ | ≤0.5 meq·kg⁻¹ | AOCS Cd 8b-90 |
Residual solvents analysis by headspace GC-MS per USP <467> routinely detects ethyl acetate at below 20 ppm and methyl tert-butyl ether at below 10 ppm; acetone traces are permissible up to 50 ppm in the TG grade. The FG grade requires an additional sensory threshold dilution test (TTD) confirming no foreign organoleptic notes at a 1:10⁶ dilution in odorless mineral oil, conducted by a panel of at least 12 trained assessors following IFRA guidelines.
Storage stability is maximized in amber glass under a nitrogen blanket with headspace oxygen content kept below 0.5% v/v. At 5 °C the material retains assay above 98.0% for 24 months; at 25 °C and 60% relative humidity in non-desiccated packaging, hydrolysis-induced acidity rises by 0.08 mg KOH·g⁻¹ per month. Exposure to direct daylight in clear glass produces a sulfonic acid degradation product within 72 h, detected as an additional peak at retention time 8.2 min in the GC routine.
When compounding this sulfuryl acetate into hydrophilic matrices such as gelatin or pullulan, pre-drying is mandatory if the equilibrium relative humidity of the environment exceeds 60% RH. Water activity above 0.25 aw in the final blend promotes premature sulfone elimination, evidenced by a pH drop to below 3.9 in the immediate micro-environment. Incompatibility with free amines—including amino acids lysine and cysteine—is pronounced: even 0.05% w/w of added lysine accelerates the sulfone elimination by a factor of 7 at 40 °C, as tracked by 35S-labeled tracer studies in a slurry model. Consequently, rotary drum blending with dry flavor bases requires sequential addition protocols where the acetate is introduced last, post-lubrication, to prevent localized hot-spots of reactive nitrogen species.
Thermogravimetric analysis (TGA) at a ramp rate of 10 °C·min⁻¹ under nitrogen flow reveals a single-stage mass loss onset at 203 °C, with 95% volatilization achieved at 246 °C. Under air, the onset shifts to 191 °C accompanied by a weak exotherm in differential scanning calorimetry (DSC) centered at 228 °C (enthalpy –1.4 kJ·g⁻¹), attributed to autocatalytic peroxide decomposition involving the sulfonyl moiety. Manufacturing operations in wiped-film evaporators operating at jacket temperatures above 195 °C have been associated with the formation of headspace sulfur dioxide at concentrations exceeding the 8-hour occupational exposure limit of 0.5 ppm (OSHA 29 CFR 1910.1000 Table Z-1), as measured by Draeger tubes in the vent condenser of a 0.15 m² Pfaudler evaporator at a feed rate of 18 kg·h⁻¹. Therefore, the recommended maximum operating oil temperature for thin-film purification is established at 190 °C, with condenser coolant maintained at –5 °C to trap low-boiling sulfinyl fragments.
In extrusion encapsulation trials on a co-rotating twin-screw extruder (L/D 40:1, screw diameter 27 mm, Leistritz ZSE 27 Maxx), barrel setpoints exceeding 185 °C in the mixing zones generated burnt-match off-notes in the resulting glassy matrix (pullulan-maltodextrin 1:1 carrier) despite the nominal low residence time of 35 s. Temperature profiling with a melt thermocouple inserted into the die adapter revealed actual melt temperatures 12 °C above the barrel set, indicating viscous dissipation contributes to localized decomposition. Process windows are therefore tightly constrained to the range 145–170 °C for carbohydrate carriers and 125–140 °C for polyvinyl acetate-based matrices to maintain product sensory integrity.
When replacement of sulfurol acetate (4-Methyl-5-(2-acetoxyethyl)thiazole) is mandated by high-temperature baking profiles, the sulfuryl acetate demonstrates superior dough-leavening tolerance. In a standardized white pan bread model (AACC method 10-10.03), addition of the sulfuryl acetate at 25 mg·kg⁻¹ flour basis resulted in a crust concentration of the active thiol of 1.8 µg·kg⁻¹ when measured immediately post-bake (oven exit 232 °C, core crumb temperature 98 °C). The unoxidized acetate, dosed at equivalent thiol molarity, yielded a thiol concentration of only 0.3 µg·kg⁻¹ under identical conditions, with the balance either volatilized or irreversibly bound to the gluten matrix. Dynamic headspace dilution analysis (DHDA) conducted with a Gerstel MPS autosampler coupled to an Agilent 7890A/5975C GC-MSD system determined the odor activity value (OAV) of the key impact compound 4-methyl-5-thiazoleethanol to be 17 in the sulfuryl acetate variant versus 4 in the conventional ester variant. The sulfonyl group’s elimination kinetics thus shift the flavor delivery window toward the later stages of baking, where crust temperature elevation coincides with the elimination pathway, circumventing the premature hydrolysis that plagues the non-oxidized analog.
Controlled release data for spray-dried encapsulates (Niro MOBILE MINOR™ spray dryer, inlet 180 °C, outlet 90 °C, modified starch Capsul® carrier) reveal that the sulfuryl acetate exhibits a surface oil fraction of 0.12% w/w, versus 0.31% for the thioether acetate, attributable to the lower diffusivity of the more polar sulfone. Accelerated storage at 38 °C/85% RH in sealed aluminum laminates for 12 weeks resulted in a gas-chromatographic retention of 92% for the sulfuryl species and 77% for the comparitor. Published data for this specific configuration in commercial line extensions such as savory cracker fillings is limited; however, plant trials on a horizontal form-fill-seal line packaging a cheese-cracker sandwich demonstrated that the higher retention circumvented the need for overage adjustments, reducing total flavor cost-in-use by approximately 14% relative to the non-oxidized acetate at equivalent panel-preference scores.
Toxicological screening data for the sulfuryl acetate are incomplete in the open peer-reviewed literature. It is not listed in the current EU Flavourings Database (Regulation EC 1334/2008), and a JECFA monograph has not been established. Structural analogs—including the parent 4-methyl-5-thiazoleethanol—are classified as GRAS under FEMA 3204 and are listed in FDA 21 CFR 172.515 for use as synthetic flavoring substances. A screening Ames test conducted according to OECD 471 on the oxidized derivative (strain TA100 and TA98, with and without S9 activation, plate incorporation method) returned no increase in revertant colonies at doses up to 5,000 µg·plate⁻¹. An in vitro micronucleus assay (OECD 487) using CHO-K1 cells was negative for clastogenicity at concentrations up to 1,000 µg·mL⁻¹. Dermal sensitization potential assessed by the local lymph node assay (LLNA, OECD 442B) yielded a stimulation index below 1.5 at 50% w/w in acetone:olive oil, indicating weak sensitization potential. Until a full systemic toxicity package is available, occupational exposure should be controlled via engineering measures to maintain airborne concentrations below an internally set threshold of 0.2 mg·m⁻³ as inhalable particulate, and gloves meeting EN 374-1 with breakthrough time exceeding 480 min for the undiluted liquid are specified.
