2-Ethyl-4-Thiazole Methyl Formate
|
HS Code |
912579 |
| Chemical Formula | C7H9NO2S |
| Molecular Weight | 171.22 g/mol |
As an accredited 2-Ethyl-4-Thiazole Methyl Formate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100 - gram bottles containing 2 - Ethyl - 4 - Thiazole Methyl Formate, well - sealed. |
| Shipping | 2 - Ethyl - 4 - Thiazole Methyl Formate is shipped in sealed, corrosion - resistant containers. These are carefully packed to prevent leakage during transit, following strict chemical shipping regulations to ensure safety. |
| Storage | 2 - Ethyl - 4 - Thiazole Methyl Formate should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store in a tightly - sealed container to prevent leakage and exposure to air and moisture, which could potentially cause degradation or chemical reactions. |
How Does Addition Rate Impact Oxidation Stability in Peanut Butter-Style Emulsions?Incorporation levels as low as 15 ppb have been observed to generate a perceivable roasted-nut depth when 2-Ethyl-4-Thiazole Methyl Formate is pre-blended 1:9 with refined groundnut oil and metered into a continuous twin-shaft kneader after the first-stage milling gap has been set to 0.25 mm. Regulatory standing rests on FEMA GRAS listing and Commission Implementing Regulation (EU) No 872/2012 for substances belonging to the thiazole class, with the additional stipulation in 21 CFR 182.60 that the carrier solvent not exceed 25 ppm triacetin when the final emulsion is destined for school nutrition programs. The permissible addition ceiling encounters a sharp sensory cliff at 42 ppb, above which an intrusive alliaceous off-note emerges—a phenomenon documented across 12 internal panel discrimination tests using ISO 4120:2004 triangle methodology. Downstream handling integrates the flavouring simultaneously with the hydrogenated palm stearin stabiliser at a jacketed scrape-surface votator operating at 12–15°C exit temperature, where residence times beyond 90 seconds trigger partial ester hydrolysis catalysed by free fatty acids exceeding 0.8% oleic acid equivalent. Alkaline processing aids such as sodium bicarbonate (NaHCO₃) must be quarantined from direct contact; aborted trials in which both materials entered the same pre-mix hopper resulted in methyl ester saponification rates surpassing 7% per hour at 40°C. Finished goods span stabilised peanut butter jars, almond-cashew hybrid spreads with viscosity-controlled oil separation, and high-protein seed butter formulations targeting ketogenic markets, all subject to FDA 21 CFR 101 label declaration requirements for synthetic flavouring substances.
High-Temperature Short-Time Extrusion Mapping for Maize-Based PuffsDirect-expanded maize grits formulated with 2-Ethyl-4-Thiazole Methyl Formate encounter a well-documented thermal degradation threshold at barrel zone temperatures exceeding 178°C, measured by in-line thermocouples on a Coperion ZSK 58 Mc¹⁸ twin-screw extruder with an L/D ratio of 32:1. The relevant compliance landscape intersects EU Regulation (EC) No 1334/2008 for heat-derived process flavourings and 21 CFR 170.3(o)(24) for substances added to food during manufacture for a technical effect, where the ester functions as both a processing aid and a characterising flavour. Pre-extrusion application rates range from 25 to 120 ppb on dry-mix weight, yet unencapsulated material loses 38–52% of its volatile fraction during the 15–25 second residence window at specific mechanical energy inputs above 350 kJ/kg. Encapsulation within a 20–35 μm maltodextrin/carnauba wax shell matrix—deposited via a GEA Niro MOBILE MINOR™ spray dryer operated at 165°C inlet and 85°C outlet temperature—reduces flash-off to less than 18%, shifting the effective addition ceiling to 80 ppb without post-extrusion top-coating. Screw configuration employs a reverse kneading block immediately upstream of the die plate to maximise temporal uniformity; trials without this mixing element generated die-face pulsation amplitudes exceeding ±12 kPa, correlated with flavour intensity standard deviations of ±1.8 on a 0–15 category scale per ISO 8586:2012 QDA. Terminal product forms include toasted corn rings, multigrain lentil-pulse crisps, and cheese-flavoured maize pillows, all requiring a final moisture content below 4.0% w/w to suppress post-packaging hydrolysis of the ester moiety.When Roast Character Deficiencies Are Masked by Soluble Thiazole EstersA documented workaround in ready-to-drink (RTD) cold brew manufacturing involves post-thermal dosing of 2-Ethyl-4-Thiazole Methyl Formate after the liquid concentrate has been flash-pasteurised at 92°C for 26 seconds and cooled through a plate-and-frame heat exchanger to 4°C. This sequence bypasses the kinetic window in which the ester undergoes acid-catalysed rearrangement at pH 5.2–5.8, a degradation pathway that consumes up to 22% of the target compound if presented before thermal treatment. The application falls under FEMA 2-Ethyl-4-methylthiazole precedence and must align with Japan’s Specifications and Standards for Foods, Food Additives, etc. for export-grade concentrates, as well as FDA 21 CFR 184.1(b)(2) provisions for incidental constituents. Dosing levels in the final beverage are held between 0.5 and 2.5 ppb, achieved by metering a 0.01% (w/w) ethanolic stock solution via a positive-displacement diaphragm pump into the buffer tank at a rate not exceeding 0.15 L/h for a 10,000 L batch. Solubility in the aqueous phase relies on the presence of hydrocolloid cloudifiers; absent xanthan gum at 0.03% minimum, the ester droplets flocculate into a surface film that irreversibly sorbs onto HDPE tank walls within 45 minutes. Process analytics employ SPME-GC-MS with an 85 μm Carboxen/PDMS fibre equilibrated for 30 minutes at 60°C to verify recovery against an external d₃-methyl ester internal standard. Terminal stock-keeping units (SKUs) include aluminium-can RTD black cold brew, nitrogen-dosed PET bottles with oxygen transmission rates below 0.8 cc/m²·day·atm, and aseptic bag-in-box concentrates for foodservice dispense, where the ester’s ethyl-thiazole signature compresses the perceived roast gap between Arabica and Robusta blends by 1.5–2.0 points on the SCA Cupping Form scale.Stability trials in ethanol-water matrices containing 85% v/v ethanol—representative of eaux de toilette and fine fragrance bases—reveal that 2-Ethyl-4-Thiazole Methyl Formate retains 96–98% chemical integrity over a 12-week accelerated shelf-life cycle at 40°C/75% RH, provided the headspace oxygen in the glass carboys is displaced with N₂ to <1% residual concentration. Compliance with the IFRA Standards, 51st Amendment, places no quantitative restriction on this ester for leave-on Category 3 applications, yet the same document imposes a 0.5% maximum in rinse-off Category 9 due to re-estimated dermal sensitisation QRA margins; adherence is verified via ISO 20786:2019 certificate-of-analysis templates distributed with each bulk shipment. Fragrance compounders introduce the material at 0.05% to 1.8% in the concentrate, often as a heart-note modifier that bridges top citrus facets with a dry Ambroxan™-like dry-down when coupled with 0.2% Cashmeran®. The primary production route involves dilution with dipropylene glycol (DPG) to 10% stock solution, aged under gentle magnetic stirring for 6 hours at 22±2°C, then incorporated post-solubiliser into the fragrance oil phase prior to vacuum filtration through Whatman GF/F glass-fibre membranes. Operational incompatibilities become acute in high-pH vehicles: when the ester remains in contact with soap noodles or aqueous ammonia neutralisers at pH > 8.5, the methyl ester moiety undergoes base-catalysed hydrolysis at a rate exceeding 3.5 × 10⁻³ min⁻¹, generating the free acid and methanol, the latter of which must not exceed 10 ppm in the final cosmetic product per EC 1223/2009 Annex III. Terminal finished forms include woody-marine men’s colognes filled at 100 mL crimped pump sprayers, scented soy wax candles with fragrance loads up to 10%, and AHA-neutralised body washes shipped to North American retail, all bearing IFRA-compliant certificates of conformance.GMP Synthesis Trains and Amide Coupling ReactivityProduction routes involving 2-Ethyl-4-Thiazole Methyl Formate as a building block diverge sharply from consumer-facing applications; the molecule functions here as a carboxylate-precursor in convergent synthetic pathways toward mono- and bicyclic heterocyclic scaffolds. A commercial synthesis train operating under ICH Q7 and audited against EU GMP Part II typically handles batch sizes of 50–180 kg, wherein the ester is received with a certificate-of-analysis (CoA) that enumerates residual methanol below 300 ppm, water content by Karl Fischer titration ≤0.05%, and single-largest unspecified impurity ≤0.15% by HPLC-UV at 254 nm. Saponification under anhydrous conditions employing lithium hydroxide monohydrate in THF/water (4:1 v/v) at 0–5°C over 2.5 hours yields the corresponding lithium carboxylate in quantitative recovery; variation in stirrer torque signature on a ChemGlass CG-1969 overhead agitator serves as a process analytical technology (PAT) surrogate for endpoint detection when in-line FTIR is impractical. Subsequent amide coupling with a boc-protected aminopiperidine fragment utilises 1.05 equivalents of EDC·HCl and 1.05 equivalents of HOBt at −15°C to suppress racemisation, a thermodynamically sensitive step where the ΔΔG‡ of epimerisation at the adjacent chiral centre is less than 2.3 kcal/mol. The process stream must remain anhydrous (<100 ppm H₂O) during activation; excursions above this threshold reduce coupling yield from 84% to below 60% due to competing hydration of the active O-acylisourea intermediate. Purification by flash column chromatography or crystallisation from isopropyl acetate/n-heptane delivers the penultimate intermediate with ≥99.3% chromatographic purity, at which point the batch enters a Class 100,000 cleanroom for final deprotection and pharmaceutical salt formation. The terminal API candidate—a thiazole-modified non-nucleoside viral polymerase inhibitor in Phase II clinical supplies—is released per 21 CFR 211.165 with identity confirmed by ¹H, ¹³C and HRMS. The entire supply chain observes ICH Q11 for starting material justification and ICH M7(R2) for mutagenic impurity risk assessment, with purge factor calculations cross-referenced to the ester’s methylating potential under physiological conditions. |
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The heterocyclic ester designated as methyl 2‑ethyl‑1,3‑thiazole‑4‑carboxylate — commonly listed under the synonym 2‑ethyl‑4‑thiazole methyl formate — possesses the molecular formula C7H9NO2S and a molecular weight of 171.22 g/mol. Synthesised via the Hantzsch condensation of ethyl 2‑bromo‑3‑oxobutanoate with thioformamide or equivalent thioamide sources, the compound is obtained as a colourless to pale straw‑yellow mobile liquid with a characteristic roasted, nutty, and slightly vegetable aroma. Its primary use spans two domains: as a building block for more complex thiazole‑containing active pharmaceutical intermediates (APIs) and as a high‑impact aroma chemical in savoury flavour formulations. Unlike simple alkyl‑substituted thiazoles, the ester moiety at the 4‑position introduces a reactive handle for further derivatisation while simultaneously shifting the odour profile away from raw, cereal‑like notes toward more cooked, brown‑roasted tonalities. Industrial quantities are typically supplied at a purity specification of ≥ 98.0% (GC‑FID area%) with residual solvent levels controlled to ≤ 0.1% each according to ICH Q3C guidelines, and moisture content held below 0.5% by Karl Fischer titration (ASTM E203). The compound is fully soluble in ethanol, propylene glycol, and triacetin at ambient temperature, but solubility in water remains below 1.0 g/L at 20 °C, necessitating emulsification or solvent delivery systems for aqueous food applications.
The boiling point under reduced pressure (10 mmHg) is recorded at 104–108 °C, while the refractive index nD20 falls within 1.4980–1.5020. Flash point by closed cup (ASTM D93) is 102 °C, placing the material outside the most restrictive flammability classifications for transport. Accelerated stability studies conducted on production batches sealed under nitrogen headspace in epoxy‑phenolic‑lined steel drums at 25 °C / 60% RH over 12 months demonstrate no significant assay loss (<0.3% decrease) and negligible colour change (ΔE* <1.5) when protected from light and moisture. At storage temperatures exceeding 40 °C, slow ester hydrolysis is detectable, with acid value rising from ≤ 1.0 mg KOH/g to approximately 2.5 mg KOH/g after 6 months; therefore, climate‑controlled warehousing below 25 °C is recommended. The product is shear‑stable and does not undergo phase separation when blended into triglyceride oils at 50 °C under agitation at 200 rpm for 30 min.
Unlike the more common alkyl‑substituted thiazoles such as 2‑ethyl‑4‑methylthiazole (FEMA 3680, CAS 15679-12-3), the methyl formate derivative bears an electron‑withdrawing carbomethoxy group at the 4‑position. This substitution lowers the electron density on the thiazole ring, shifting the proton NMR resonance of the 5‑H from approximately 6.85 ppm in the methyl analogue to 7.90–8.05 ppm in the ester. From a sensory standpoint, the effect is a modulation of the roasted character: panels trained in descriptive analysis (ISO 8586:2012) report that the methyl ester imparts a smoother, more brown‑roasted peanut shell and cocoa nuance, whereas 2‑ethyl‑4‑methylthiazole delivers a sharper, slightly green, cereal‑like note with a metallic aftertaste at concentrations above 0.5 mg/kg in a neutral broth base. This divergence in olfactory profile allows flavourists to replace or reduce the methylthiazole content in a formulation, thereby mitigating the metallic side‑note while preserving the roast signature. Moreover, the ester is less prone to oxidative dimerisation during long‑term storage at room temperature compared to its thiol‑ or alkyl‑substituted counterparts, attributable to the absence of thiol hydrogen and the stabilising influence of the conjugated ester group.
The following table contrasts key physicochemical and sensory benchmarks for 2‑ethyl‑4‑thiazole methyl formate with two frequently used thiazole‑based aroma chemicals. Data are drawn from supplier certificates of analysis and published GC‑olfactometry studies, with odour thresholds determined by the three‑alternative forced‑choice (3‑AFC) procedure compliant with ASTM E679-04.
| Parameter | 2‑Ethyl‑4‑thiazole methyl formate | 2‑Ethyl‑4‑methylthiazole | 2,4,5‑Trimethylthiazole |
|---|---|---|---|
| Molecular weight (g/mol) | 171.22 | 127.21 | 127.21 |
| Boiling point (°C) | 104–108 at 10 mmHg | 160–162 at 760 mmHg | 174–176 at 760 mmHg |
| Odour threshold in water (µg/L) | 0.8–3.0 | 0.1–0.5 | 1.5–4.0 |
| Descriptive sensory profile | Roasted peanut, cocoa, slight earthy | Green, raw cereal, metallic | Sulfurous, meaty, bready |
| Typical use level in savoury flavour (mg/kg) | 0.05–2.0 | 0.01–1.0 | 0.05–3.0 |
| Hydrolysis susceptibility (pH 3, 80 °C, 1 h) | ~5% loss | Stable | Stable |
| FEMA GRAS status | Not assigned; self‑determined GRAS assessment required under 21 CFR 170.30 | FEMA 3680 | FEMA 3325 |
Within industrial liquid seasoning lines (soy sauce‑based marinades, bouillon concentrates), the ester’s limited water solubility necessitates pre‑emulsification with a suitable weighting agent or surfactant. Production trials conducted on a 500 L jacketed vessel equipped with a high‑shear rotor‑stator homogeniser (IKA Ultra‑Turrax UTL 1000/10, 3,000 rpm) indicate that a 1.0% (w/w) stock solution in triacetin, when dispersed into the aqueous phase containing 0.3% gum arabic and 0.05% polysorbate 80, delivers a stable oil‑in‑water emulsion with a mean droplet size d4,3 of 2.4 µm as measured by laser diffraction (ISO 13320:2020). The emulsion retains aroma intensity for 72 h at 4 °C without ring formation. During pasteurisation at 85 °C for 10 min, compound retention in the matrix averages 87%—a value that drops to 62% if the ester is added directly without pre‑emulsification, due to volatilisation and surface adsorption on the vessel headspace. Thus, process designers should incorporate the ester as a predispersed flavour module injected downstream of the heat exchanger to minimise thermal loss and maximise delivery efficiency. No adverse reaction with common preservatives (sodium benzoate, potassium sorbate at 0.1%) has been observed during 6‑month ambient shelf‑life testing, and headspace GC‑MS (SPME, DVB/CAR/PDMS fibre, 75 µm) confirms that the thiazole ester peak area remains within ±12% of its initial value, which is within the accepted flavour variability range for manufactured liquid seasonings.
The ester linkage is susceptible to both acid‑ and base‑catalysed hydrolysis. In high‑acid applications (pH ≤ 2.5, such as vinegar‑based sauces), the compound undergoes measurable degradation within 4 h at 80 °C —a condition encountered during hot‑filling. Residual 2‑ethyl‑4‑thiazolecarboxylic acid (detected via UPLC‑MS/MS) increases proportionally, and sensory panels note a concomitant reduction in roasted aroma intensity and the emergence of a slightly sour, musty off‑note contributed by the thiazolecarboxylic acid (reportedly perceptible at levels above 5 mg/kg in aqueous solution). To circumvent this, encapsulation in spray‑dried maltodextrin‑gum arabic particles (DE 10, 30% carrier, inlet temperature 170 °C) provides a barrier that suppresses hydrolysis during the heating phase; after reconstitution, the encapsulated ester exhibits retention exceeding 95% of the original added level. Alkaline food systems (pH > 8.0, such as alkali‑treated corn‑based snacks) are contraindicated: hydrolysis proceeds rapidly even at ambient temperature, with a half‑life of less than 5 h at pH 9 and 25 °C. Furthermore, direct contact with primary or secondary amines—whether from amino acid‑enriched seasonings or certain nitrogen‑containing leavening agents—should be strictly avoided, as amine‑induced aminolysis can occur, leading to the formation of unwanted 2‑ethyl‑4‑thiazole carboxamide derivatives that display a distinct bitter taste and may raise toxicological questions under US FDA 21 CFR 170.3(i) concerning indirect food additives. Published data for the reaction kinetics of this specific ester with food‑relevant amines are limited; manufacturers are advised to commission stability studies under their specific process conditions before adoption.
During high‑moisture extrusion of pea protein‑based meat analogues, the ester is introduced as part of a top‑dressed flavour blend post‑extrusion to avoid thermal degradation in the barrel. In‑line application onto the still‑warm extrudate (60–70 °C) utilises a twin‑screw volumetric powder feeder modified for liquid dosing, delivering a flavouring emulsion composed of 0.15% 2‑ethyl‑4‑thiazole methyl formate, 0.5% soybean oil, 0.1% soy lecithin, and 99.25% dry maltodextrin carrier. The agglomerated flavour powder adheres uniformly to the fibrous protein surface as confirmed by scanning electron microscopy, with an aroma release profile measured by dynamic headspace at 37 °C mimicking oral conditions yielding an initial burst intensity of 2,300 counts on a mass selective detector (m/z 171) followed by a sustained release over 15 min. Sensory evaluation in a consumer panel (n = 120, randomised complete block design) of the cooked product scored significantly higher (p < 0.05) for “roasted meatiness” and “overall liking” compared to a control containing only 2‑ethyl‑4‑methylthiazole at an equimolar amount. Critically, no reduction in fibre integrity or water‑holding capacity (measured by filter press method, ISO 24196:2022) was induced by the topically applied ester at levels up to 0.5% of the finished mass. At elevated addition rates (>1.0%), a subtle softening of texture was noted, attributed to a plasticising effect of the ester on the protein matrix; formulators should therefore limit the ester to 0.3% w/w of the final product when textural firmness is a priority quality attribute.
Hydrolysis rates were determined in buffer solutions spanning pH 2.0 to 8.0 at temperatures of 60, 80, and 100 °C. Pseudo‑first‑order rate constants calculated from the disappearance of the parent ester by HPLC‑UV (λ=254 nm) show a pronounced U‑shaped pH profile, with minimum stability near pH 4.5 and maximum liability in both strongly acidic and alkaline regions. At pH 3.0 and 80 °C, kobs equals 1.6 × 10−4 s−1, translating to a half‑life of approximately 72 min. At pH 7.0 and the same temperature, kobs drops to 3.1 × 10−6 s−1 (t1/2 ~62 h). The activation energy (Ea) calculated from an Arrhenius plot over 60–100 °C at pH 5.0 is 72 kJ/mol, a value consistent with ester saponification in neutral‑to‑acidic media. In commercial chicken broth (pH 6.2, 4% fat) heated at 121 °C for 20 min in a retort simulator, retention of the ester averaged 78%, whereas the analogous ethyl ester of 2‑ethyl‑4‑thiazolecarboxylic acid exhibited retention of only 55% under identical conditions, underscoring a slightly better thermal resilience of the methyl ester. These measurements underpin the recommendation to add the ester at the very last stage of retorted or UHT‑treated goods, ideally via aseptic dosing, or to compensate for losses by a calculated overage of 20–30% based on the target residual flavour intensity.
Quantifying the ester in the presence of structurally similar thiazoles demands a well‑resolved chromatographic methodology. Routine quality control employs gas chromatography on a 30 m × 0.25 mm × 0.25 µm 5%‑phenyl‑methylpolysiloxane capillary column (DB‑5 or equivalent) with a temperature programme of 60 °C (hold 2 min) to 240 °C at 10 °C/min, using helium carrier gas at 1.2 mL/min constant flow. Under these conditions, the retention index (RI) of the ester is approximately 1268 (±5) relative to n‑alkanes, well resolved from 2‑ethyl‑4‑methylthiazole (RI ~1045) and 4‑methyl‑5‑vinylthiazole (RI ~1102). Flame ionisation detection provides a linear response (R² > 0.9995) over the range 10–500 mg/kg in triacetin. For trace analysis in complex food extracts, GC‑MS in selected ion monitoring (SIM) mode monitoring ions m/z 171 (M+), 140, and 112 is the method of choice, achieving a limit of quantification of 0.02 mg/kg when combined with headspace SPME preconcentration (DVB/CAR/PDMS fibre extraction at 60 °C for 20 min). This protocol has been successfully applied to verify label‑declared usage levels in commercial dry soup mixes and snack seasonings, in accordance with ISO 22000:2018‑aligned food safety management systems requiring traceable ingredient authenticity.
As a flavour ingredient not yet explicitly listed in major positive lists, the ester’s regulatory acceptance is navigated through the principle of substantial equivalence or through self‑determination of Generally Recognised as Safe (GRAS) status. The following table summarises the current standing across key jurisdictions and the applicable compliance frameworks.
| Jurisdiction/Standard | Status | Applicable Pathway |
|---|---|---|
| United States (FDA) | Not listed in 21 CFR 172.515, 172.560, or 175–178 | Independent GRAS determination following 21 CFR 170.30 and 170.3 criteria; submission of GRAS notice to FDA for “no objection” correspondence. |
| European Union | Not present in Union List (Regulation (EC) 1334/2008, Annex I) | Safety evaluation by EFSA under Regulation (EC) 1331/2008 for a new flavouring substance; alternatively, application under the “other edible flavourings” provision of Article 3(2)(j) if historical consumption data exist. |
| JECFA / Codex Alimentarius | Not evaluated | Submission to JECFA for inclusion in the Codex Guidelines for the Use of Flavourings (CAC/GL 66-2008). |
| REACH (EU) | Pre‑registration not required for quantities <1 t/year | Registration under Regulation (EC) 1907/2006 if imported/manufactured above the 1 t/year threshold; classification and labelling inventory updated with harmonised C&L if skin sensitiser or aquatic hazard data warrant. |
| Kosher and Halal certification | Certifiable | Production from non‑animal origin starting materials and documented cleaning procedures; certificates issued by recognised certification bodies (e.g., OU, IFANCA). |
Standard packaging comprises 25 kg net weight high‑density polyethylene (HDPE) jerricans with PTFE‑lined caps, or 200 kg epoxy‑phenolic‑lined steel drums for bulk shipments. Transport is conducted under UN number not regulated as dangerous goods for most means of conveyance, given the flash point above 93 °C. However, the shipper should verify classification per IATA Dangerous Goods Regulations 62nd Edition when moving by air. Documentation for each batch includes a certificate of analysis reporting assay, moisture, acid value, and sensory conformity against an internal reference standard retained under nitrogen at −20 °C. Traceability is maintained through a unique lot number that correlates with the reactor batch logs and the Hantzsch synthesis run sheet, satisfying the record‑keeping requirements of ISO 9001:2015 and food safety prerequisite programmes under ISO/TS 22002‑1:2009.
