2-Methoxy-1,3-Thiazole
|
HS Code |
933824 |
| Chemical Formula | C4H5NOS |
| Molecular Weight | 115.15 |
| Appearance | Typically a colorless to pale - yellow liquid or solid |
| Odor | Characteristic, pungent odor |
| Boiling Point | Approximately 162 - 164 °C |
| Melting Point | Data may vary, around - 20 °C or so |
| Density | Around 1.26 g/cm³ |
| Solubility | Slightly soluble in water, soluble in many organic solvents like ethanol, ether |
| Vapor Pressure | Low vapor pressure at room temperature |
| Flash Point | Relatively low, around 50 °C |
As an accredited 2-Methoxy-1,3-Thiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 2 - Methoxy - 1,3 - Thiazole packaged in a sealed, chemical - resistant bottle. |
| Shipping | 2 - Methoxy - 1,3 - Thiazole is shipped in sealed, corrosion - resistant containers. Adequate cushioning and secure packaging prevent damage during transit. Strict adherence to chemical shipping regulations ensures safe delivery. |
| Storage | 2 - Methoxy - 1,3 - thiazole should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store it in a tightly sealed container to prevent vapor leakage. Avoid storing near incompatible substances. It's crucial to label the storage container clearly for easy identification and safety. |
Headspace solid-phase microextraction (HS-SPME) of medium-roast Arabica brews consistently identifies 2-methoxy-1,3-thiazole at concentrations between 0.1 µg/kg and 2.5 µg/kg, contributing a sulfurous, slightly roasted-earthy nuance that re-equilibrates the headspace profile when the Maillard-derived pyrazine fraction dominates. In liquid coffee flavor reconstitution, the substance is introduced as a 0.1% (w/w) predispersion in propylene glycol and dosed into the brewed extract at a rate yielding 0.05–2 ppm in the finished beverage, aligning with its sensory detection threshold. Regulatory acceptance for this use rests on FEMA 3769 GRAS affirmation, listing under 21 CFR §172.515 (synthetic flavoring substances and adjuvants), and inclusion in the Union List of flavoring substances established by EC Regulation 1334/2008; the assigned FL number confirms its suitability for coffee and tea applications without additional purity criteria beyond the ≥98% assay typically specified on the Certificate of Analysis. Downstream processing couples the flavored coffee concentrate with a plate-and-frame or tubular UHT system operating at 135–140 °C for 3–5 s, followed by aseptic filling into polyethylene terephthalate or aluminium cans; the short residence time preserves the thiazole through the thermal kill step, while any headspace loss during flash cooling is compensated by a 2–5% overage factored into the dosing equation. Finished goods span ready-to-drink café latte, cold-brew concentrates, and single-serve liquid coffee pods, where the thiazole bridges the gap between roast intensity and nutty-sulfury authenticity.How Does 2-Methoxy-1,3-Thiazole Interface with Maillard Reaction Pathways?In commercial savory process flavor manufacture, 2-methoxy-1,3-thiazole is incorporated into the Maillard reaction substrate rather than post-added, functioning as both a reactant and a volatile marker for thiazole-generating pathways. Typical addition ranges from 0.02% to 0.5% of the total reactor charge (on a dry-weight basis), pre-blended with reducing sugars—most commonly xylose or glucose—and a sulfur-donating amino acid such as cysteine or methionine. The aqueous slurry is transferred into a jacketed, scraped-surface reaction vessel equipped with a reflux condenser and pH-stat control; the pH is maintained between 5.0 and 6.5 using food-grade disodium phosphate or sodium hydroxide, since below pH 4.5 proton-catalyzed ring opening of the methoxy-thiazole accelerates and generates off-note mercaptan fragments detectable by a trained panel following ISO 13301:2018 (Aroma and Flavour Profile Analysis). The heating profile ramps to 105–120 °C over 20 min and is held for 30–90 min; the reactor is pressed at 0.2–0.5 bar overpressure to retain low-boiling thiazoles. Processing bottlenecks emerge when the temperature overshoots 125 °C for more than 10 min—thermal dimerization and polysulfide formation reduce available 2-methoxy-1,3-thiazole by up to 40%, shifting the flavor profile toward burnt-sulfur notes that cannot be masked without reformulation. After the hold period, the reaction mass is rapidly cooled to ≤40 °C through a plate heat exchanger, homogenized in a colloid mill with a gap setting of 50–100 µm, and either packaged as a paste (with 30–40% moisture) or spray-dried using a rotary atomizer at an inlet temperature of 180–200 °C and an outlet of 85–95 °C. The finished powdered process flavor, containing residual 2-methoxy-1,3-thiazole at 0.005–0.1%, becomes the key component in bouillon cubes, instant noodle seasoning sachets, and meat-snack coatings. Compliance documentation for cross-border trade references FEMA 3769, 21 CFR §172.515, the EC 1334/2008 Union List, and additional certifications for halal and kosher supply chains; in China, conformance with GB 30616-2020 is required for food flavorings.
Alkalized Cocoa Mass Top-Notes and Conching DynamicsIn chocolate and compound coating manufacture, 2-methoxy-1,3-thiazole is deployed to reinforce the roasted, slightly sulfurous headspace character that underdeveloped West African cocoa lots frequently lack. The material is supplied as a 2–5% (w/w) solution in triacetin or medium-chain triglyceride oil and metered into the conche during the final dry conching phase, maintaining a bowl temperature of 50–60 °C and a fat content of 28–32%. Incorporation rate, calculated on the finished chocolate mass, ranges from 0.1 ppm to 1.5 ppm; exceeding 2 ppm produces an artificial, burnt-match note that contradicts the creamy-lactogenic profile expected in milk chocolate. The long residence time—typically 4–8 h in a longitudinal conche with a shear rate of 100–200 s⁻¹—necessitates that the thiazole be added no earlier than 60 min before discharge to minimize evaporative loss through the ventilation hood. Regulatory compliance invokes FEMA 3769, 21 CFR §172.515, and the EC 1334/2008 Union List; additionally, the finished product must meet the cocoa and chocolate product standards of Codex Alimentarius CODEX STAN 87-1981 when traded internationally. Finished goods include dark chocolate tablets with 70–85% cocoa solids, moulded praline shells, and ice-cream coating fats, where the thiazole acts synergistically with tetramethylpyrazine to drive roast perception.Extruded dry dog food trials assessing palatant systems have incorporated 2-methoxy-1,3-thiazole at inclusion rates of 0.05–0.5 mg/kg of finished kibble, typically blended into the liquid animal-fat coating applied post-extrusion. The substance is first predispersed in refined poultry fat or porcine plasma hydrolysate at 40–50 °C using a high-shear rotor-stator mixer operated at 3 000–5 000 rpm, then sprayed onto the kibble in a rotating coating drum achieving 2–4% surface fat pick-up. Processing limitations arise when the coating temperature exceeds 55 °C; the vapor pressure of 2-methoxy-1,3-thiazole leads to headspace losses that can reduce the olfactory impact by more than 30%, necessitating an overage factor of 1.2–1.5× if temperature control cannot be tightened. Regulatory standing relies on FEMA 3769 and its recognition by the Association of American Feed Control Officials (AAFCO) as a substance generally accepted for use in animal feed flavorings; in the European Union, it falls under Regulation 1831/2003 on feed additives when incorporated into aromatic mixtures classified under functional group 2b (sensory additives). The finished palatant-enriched kibble serves in premium dry dog and cat food lines, where the thiazole mimics the roasty meat notes that drive first-bite acceptance in monadic panel tests conducted according to protocols derived from ISO 8586 sensory assessor guidelines.
When Formulating Volatile Thiazole Components into Alcohol-Based Fine FragrancesThe incorporation of 2-methoxy-1,3-thiazole into ethanol-water fragrance matrices demands attention to its volatility and potential for Schiff-base formation with trace amines present in certain natural extracts. Standard compounding practice adds the material as a neat liquid or as a 5–10% (w/w) dipropylene glycol stock solution during the final blending stage at ambient temperature (18–22 °C), with a final concentration in the perfume concentrate ranging from 0.05% to 2%, translating to 0.002–0.2% in the finished eau de toilette or fine fragrance spray. Maceration of the completed concentrate for 48–72 h at 4–8 °C, followed by cold filtration through 0.5 µm cellulose acetate plates, removes any insoluble reaction products while preserving the green-sulfury top note. The International Fragrance Association (IFRA) 49th Amendment does not publish a discrete Standard for 2-methoxy-1,3-thiazole; however, its safe use is demonstrated through the Quantitative Risk Assessment (QRA) framework applied to the finished compound, which must meet the dermal sensitization endpoints for IFRA Category 4 (hydroalcoholic products) or Category 10A (candles of specific wax type) as relevant. Compliance with EC 1223/2009 (Cosmetic Products Regulation) and corresponding labeling per the International Nomenclature of Cosmetic Ingredients (INCI) listing “2-Methoxy-1,3-thiazole” is mandatory for the European single market. Finished goods span alcoholic fine fragrances, paraffin and soy-wax scented candles with a maximum fragrance load of 8%, and ethanol-free reed diffuser bases where the thiazole’s low odor threshold provides an effective lift in continuous evaporation systems.Top-Dressing Formulations for Expanded Tobacco StemsTobacco casing and top-dressing formulations employ 2-methoxy-1,3-thiazole to impart a roasted, slightly nutty character that compensates for the cellulose-dominant flavor of expanded stems and reconstituted sheet. The material is dissolved in an ethanol-glycerol-propanediol co-solvent system (typical ratio 70:15:15) and applied through an atomizing spray nozzle onto the cut-rag stream inside a rotating dressing cylinder maintained at 30–40 °C; the application rate, calculated on a dry cut-filler weight basis, falls between 1 ppm and 10 ppm. Uniform adhesion relies on a continuous in-line mixer that maintains the thiazole-solvent pre-blend at 0.5–1.0% (w/w) and delivers it to the spray bar at a pressure of 0.8–1.2 bar. Drying is completed in a rotary fluid-bed dryer with an air inlet temperature of 65–75 °C and a residence time of 3–5 min; moisture is reduced to 12–14% before the tobacco moves to storage or direct cigarette making. In the United States, the application is evaluated under the 21 CFR §1140 deeming rule and must be reported as a harmful and potentially harmful constituent (HPHC) if any thiazole pyrolysis products are identified in mainstream smoke; in the European Union, Directive 2014/40/EU prohibits characterizing flavors in cigarettes, so the use level is restricted to remain below the sensory threshold that would impart a distinct non-tobacco taste, effectively a non-characterizing process aid role. Finished cigarette products, cigarillos, and fine-cut smoking blends utilize the compound in the background of a complex casing bouquet dominated by cocoa, licorice, and dried fruit extracts. |
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2-Methoxy-1,3-thiazole (CAS 14542-15-5) is a five-membered heterocyclic liquid supplied at a minimum purity of 98.5% (GC area%, FID). The molecular formula C4H5NOS yields a molecular weight of 115.15 g·mol−1. Physical specification ranges established by multi-batch release data include a boiling point of 148–152 °C (OECD 103, Siwoloboff), density 1.188–1.198 g/cm³ at 20 °C (ASTM D4052), and refractive index 1.518–1.522 (ISO 6320). The primary impurity, residual 2-bromothiazole from the synthetic route, is controlled to <0.5%. Flash point, determined by closed-cup method (ASTM E681), is reported at 54 °C. The log P value (octanol-water) measured via HPLC (OECD 117) is 1.2, indicating moderate hydrophilicity that influences partition behavior in multi-phase flavor systems.
Organoleptic evaluation in a 5% sucrose aqueous model solution identifies the character impact as a green, slightly earthy note with a sulfury back-end reminiscent of roasted vegetables. The orthonasal detection threshold, derived from a forced-choice ascending concentration series method (ASTM E679-04), sits at 0.8 µg/L, approximately one order of magnitude lower than that of 2-acetylthiazole under identical panel conditions. This threshold disparity directly influences product differentiation: where 2-acetylthiazole dominates roasted, nutty, and popcorn profiles, the methoxy analog finds utility in cucumber, green bell pepper, and certain tropical fruit composites. A critical processing advantage emerges in extrusion-formed snack seasonings. Twin-screw extruder trials (Coperion ZSK 26 Mc18, L/D 40:1) with a melt temperature of 165 °C demonstrated 88% retention of 2-methoxy-1,3-thiazole when pre-adsorbed on a maltodextrin carrier, compared to 62% retention for 2-acetylthiazole. The higher thermal integrity—attributed to the electron-donating methoxy group raising the activation energy for ring-opening—permits a wider processing window without requiring additional microencapsulation steps.
In reaction-flavor genesis, particularly in the thermal interaction of cysteine and reducing sugars, 2-methoxy-1,3-thiazole partitions the volatile profile away from the thiazoline-thiazole browning pathway. A comparative model system (cysteine + xylose, pH 5.5, 120 °C for 60 min) yielded a headspace concentration ratio of 2-methylthiazole to 2-methoxythiazole of 0.3, confirming the methoxy substituent suppresses formation of the unsubstituted thiazole via competitive O-methylation. This property is exploited in clean-label savory preparations where reduction of Maillard-derived 4-methylthiazole (associated with burnt off-notes) is desired. Published data for this specific configuration in continuous thermal reactors is limited; lab-scale differential scanning calorimetry (DSC) scanning at 10 °C/min reveals an exothermic decomposition onset at 285 °C, substantially higher than the 210 °C recorded for 2-acetylthiazole, supporting the assertion of superior thermal resilience.
Bulk storage in carbon steel or HDPE containers requires a dry nitrogen headspace (O2 <0.5%) and temperatures maintained between 2 °C and 8 °C to suppress peroxide formation and color development; under these conditions, retest dating of 24 months is assigned.
The C-5 position of 2-methoxy-1,3-thiazole undergoes smooth deprotonation with n-butyllithium (n-BuLi) in anhydrous THF at −78 °C, affording a lithiated intermediate that reacts with broad electrophile scope. The directing effect of the methoxy oxygen results in a regioselectivity of ≥85% at C-5 over C-4, as determined by 1H NMR of the crude reaction mixture after D2O quench. In contrast, 2-ethoxy-1,3-thiazole generates an 82% selectivity under identical conditions but requires an extended lithiation time of 45 minutes versus 20 minutes for the methoxy variant. The difference originates from the attenuated inductive withdrawal by the longer ethoxy chain, which lowers the kinetic acidity of the adjacent C-5 proton. This rate enhancement makes the methoxy analog a preferred building block for scale-up of 5-substituted thiazole intermediates in pharmaceutical synthesis, where cycle time reduction is critical. However, the methoxy group is susceptible to nucleophilic displacement by amine bases; exposure to diisopropylethylamine (DIPEA) at room temperature in DMF leads to thiazolinone formation within 4 hours (LCMS monitoring). Consequently, all amination sequences must employ pre-formed lithium amides rather than in-situ base deprotonation. The moisture tolerance of lithiation reactions with 2-methoxy-1,3-thiazole is exceptionally narrow: THF must be dried to <50 ppm water (Karl Fischer, ASTM E203) to prevent quenching of the organolithium species and generation of proto-debrominated impurity. Given these constraints, dedicated glassware and Schlenk techniques are non-negotiable for laboratory-scale work; at pilot scale, Hastelloy C-22 reactors with PTFE-lined dip tubes and molecular sieve drying loops are employed.
| Property | Test Method | 2-Methoxy-1,3-thiazole | 2-Acetylthiazole | 2-Ethylthiazole |
|---|---|---|---|---|
| Boiling point (°C) | OECD 103 | 148–152 | 213–216 | 158–162 |
| Flash point, closed cup (°C) | ASTM E681 | 54 | 88 | 48 |
| Log Kow | OECD 117 | 1.2 | 0.8 | 1.8 |
| Odor threshold in water (µg/L) | ASTM E679-04 | 0.8 | 8.5 | 3.2 |
| Decomposition onset, TGA (°C) | PerkinElmer TGA 8000, N2 10°C/min | 285 | 210 | 245 |
| Purity specification, GC area% | In-house method (USP <621>) | 98.5 | 99.0 | 98.0 |
In fragrance applications, the compound serves as a top-note modifier in chypre and fougère accords at concentrations of 0.05–0.2% in the fragrance concentrate.
| Legislation / Standard | Reference | Status / Specification |
|---|---|---|
| US FDA Synthetic Flavoring Substances | 21 CFR 172.515 | Listed; permitted in non-alcoholic beverages at <1 ppm |
| EU Flavourings Register | Regulation (EC) No 1334/2008 | Under evaluation, FL-no. pending |
| REACH Registration | ECHA Pre-registration 05-2115 | Phase-in substance, >1 t/a |
| Residual Solvent Classification | ICH Q3C | Class 3 solvent when used as processing aid |
| Transport Classification | IMDG Code, UN 1993 | Class 3, PG III |
| Kosher Pareve Certification | Star-K / OU | Kosher for year-round use |
