4-Methyl-6-Thiazoleethanol(Meat)
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HS Code |
631722 |
| Chemical Formula | C6H9NOS |
| Molecular Weight | 143.21 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Meaty, savory odor |
| Solubility In Water | Slightly soluble |
| Solubility In Organic Solvents | Soluble in many organic solvents |
| Boiling Point | 115 - 117 °C at 13 mmHg |
| Flash Point | 94 °C |
| Density | 1.144 g/cm³ at 25 °C |
| Vapor Pressure | Low |
As an accredited 4-Methyl-6-Thiazoleethanol(Meat) factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 500g of 4 - Methyl - 6 - Thiazoleethanol (Meat) packaged in an air - tight plastic container. |
| Shipping | 4 - Methyl - 6 - Thiazoleethanol (Meat) is shipped in accordance with strict chemical transportation regulations. It's carefully packaged to prevent leakage, transported in approved containers, and handled by carriers with relevant hazardous material shipping expertise. |
| Storage | 4 - Methyl - 6 - Thiazoleethanol (Meat) should be stored in a cool, dry place away from direct sunlight. Keep it in a tightly - sealed container to prevent evaporation and contamination. Store it separately from incompatible substances like oxidizing agents. Ideal storage temperature is around 2 - 8°C if refrigeration is possible to maintain its stability. |
In reaction flavor manufacture, 4-Methyl-6-Thiazoleethanol (Meat) is dosed into aqueous precursor mixtures containing reducing sugars, amino acid sources, and hydrolyzed vegetable proteins prior to thermal processing. The addition rate measured against finished reaction flavor mass typically falls between 0.02 wt% and 0.15 wt%, equivalent to 200–1,500 ppm in the liquid concentrate. Thermal reaction vessels operating at 105–120°C for 60–180 min under pH 5.0–6.2 enable incorporation into the melanoidin matrix without triggering premature sulfur loss. The compound’s free thiazole ethanol moiety participates in Maillard cascade termination reactions that lock the sulfurol-like character into a delayed-release form, a phenomenon exploited in industrialized continuous stirred-tank reactors fitted with reflux condensers set to return volatile fractions below 98°C. Compliance for process flavor applications rests on the thermolytic generation exemption under Regulation (EC) No 1334/2008 Article 3, where the resulting flavoring preparation is labeled as “natural flavoring” only if precursors meet natural qualification criteria; the neat substance retains FEMA GRAS 3204 status and is listed in JECFA monograph 1031 with an ADI of 0–0.5 mg/kg bw. Production-scale observations from 1,000 L jacketed reactors indicate batch-to-batch retronasal intensity variation narrows when the precursor slurry is homogenized at ≥2,000 rpm for no less than 5 min before ramp heating begins. Finished process flavors are usually spray-dried onto maltodextrin DE 12–18 carriers at inlet temperatures not exceeding 185°C to avoid thermal desorption of the embedded volatiles, yielding free-flowing powders destined for dry soup mixes, bouillon cubes, and seasoning sachets for instant noodles.How does a thiazole-driven meat note redistribute in extruded high-moisture plant protein matrices? When 4-Methyl-6-Thiazoleethanol (Meat) is pre-emulsified with a small-molecule carrier oil and injected into the conditioning cylinder of a twin-screw extruder processing textured vegetable protein, the partitioning coefficient between the vapor phase and the wet protein melt determines fidelity of the roasted beef top note. Direct injection during extrusion at barrel zone temperatures of 130–155°C results in instantaneous vaporization losses exceeding 45% unless the compound is entrapped in a food-grade encapsulant with glass transition temperature above the die exit temperature. Pre-coating of the pea or soy protein isolate with an emulsion containing 0.08–0.25 g of 4-Methyl-6-Thiazoleethanol per kilogram of dry protein and a blend of gum arabic and enzymatically modified starch at a core-to-wall ratio of 1:3 reduces flash-off measured via headspace GC-MS by at least 32% compared to neat addition. The final formed meat analogue, after cooling and partial dehydration to 58–63% moisture, delivers a validated grilled pork or medium-rare beef aroma character when reconstituted and pan-fried. Regulatory positioning in this segment must acknowledge that the EU Flavis number 15.126 covers the substance for food categories including meat analogues in dilutions well below the taste threshold of 0.5 ppb in the water phase. Production facilities subject to FSMA preventive controls must verify that residual solvent levels from synthetic routes comply with USP <467> limits, with typical residual 2-butanone staying under 5 µg/g. Accelerated shelf-life testing at 40°C/75% RH for 12 weeks in three-layer metallized pouches documented a sensorial half-life of 9–11 weeks for the roasted character, placing a hard limit on unrefrigerated distribution timelines in tropical markets.Bouillon Cube and Dry Soup Base Formulation ConstraintsGranular bouillon cubes pressed from mixtures of salt, monosodium glutamate, hydrogenated palm fat, and dehydrated vegetables require a completely homogenous distribution of 4-Methyl-6-Thiazoleethanol (Meat) to avoid hot spots that deliver an overpowering liver-like off-note upon dissolution. Ploughshare mixers with chopper blades running at 1,500–3,000 rpm achieve a coefficient of variation below 5% for a target concentration of 0.3–0.8 mg/kg in the dry blend when the flavor is first triturated with a microcrystalline cellulose carrier in a 1:9 ratio. The European Commission Directive 2008/60/EC establishing purity criteria specifies that the compound shall contain not less than 97% assay (GC), which becomes critical for low-dosage mixes because impurities such as 4-methylthiazole can shift the overall profile toward burnt rubber rather than roasted meat. During cube compression on rotary tablet presses exerting 8–12 kN compression force per station, the molecule’s crystalline nature at ambient temperature aids uniform dispersion but can cause lamination of the cube surface if the press speed exceeds 45 rpm; pre-blending the compound with a vegetable fat coating melt at 42–48°C prior to incorporation into the dry mass resolves this mechanical failure. The reconstitution behavior in boiling water at 95–99°C yields an initial burst of volatile thiazole note within 30 seconds, followed by a sustained ten-minute release plateau measurable by dynamic headspace sampling combined with atmospheric pressure chemical ionization–time-of-flight MS. For EU market authorization, the finished bouillon cube falls under the horizontal legislation on food flavorings, with the compound classified as flavoring substance FL 15.126, carrying no specific numerical maximum except quantum satis compliance, but labelling must declare its FL number if sold as a proprietary flavoring blend exceeding 0.1% in the ready-to-consume broth.Corrosion-prone carbon steel feed lines in pet food gravy production have been documented to react with sulfur-containing thiazole compounds at temperatures above 85°C, creating iron sulfide microparticulates that quench aroma intensity and require passivation or substitution with 316L stainless steel. 4-Methyl-6-Thiazoleethanol (Meat) is applied in wet cat and dog food recipes at 0.04–0.12 mg/kg of the retorted product, typically co-emulsified with tallow and mechanically homogenized at 150–250 bar before injection into the filler stream post-grinding. The combination with sodium tripolyphosphate at 0.3% improves retention of the sulfurous meat character through the retort process at 121°C for 45 min, as phosphate sequesters pro-oxidant metal ions that catalyze thiazole ring-opening. AAFCO ingredient definition guidelines treat the compound as a “flavoring” with no numerical upper constraint, but a two-bowl preference test according to ISO 6658:2017 demonstrates that intake ratio drops below 55:45 when the compound concentration in the finished loaf exceeds 0.30 mg/kg, at which point cats exhibit neophobia toward the sulfur-heavy top note. Stability trials at commercial canneries indicate that zinc oxide-coated can interiors extend the compound’s half-life by 3.7-fold over plain tinplate, attributable to suppression of thiazole adsorption onto tin oxides. For export into the Japanese market, compliance with the Pet Food Safety Law and the standards set by the Japan Pet Food Association requires a certificate of analysis that includes aflatoxin B1, arsenic, and heavy metals testing, along with a declaration that the flavor component is not sourced from bovine or ovine origin materials.
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Introduced into commercial flavor portfolios under the trade identifier 4-Methyl-6-thiazoleethanol, this heterocyclic compound supplies the sulfide-tinged, roasted-meat character required in high-temperature savory systems. Distilled to a minimum purity of 98% (GC area%, FID detection), the substance appears as a pale amber to yellow liquid with a characteristic sulfury, beefy odor and a taste threshold in water below 0.5 ppb. Its molecular formula C6H9NOS and a molecular weight of 143.21 g·mol−1 place it among the smaller thiazole odorants, facilitating rapid vapor-phase partitioning during extrusion or retorting. Unlike the more common 5-substituted isomer, the 6-methyl configuration shifts the odor profile toward roasted, slightly nutty facets while suppressing the alliaceous pungency found in 4-methyl-5-vinylthiazole. This positional isomerism becomes critical when formulating clean-label meat analogs, where top-note authenticity must be achieved without the sulfidic overlay that panelists associate with over-cooked garlic.
In thiazole chemistry, the position of the methyl substituent relative to the ethanol side chain governs both the molecule’s dipole moment and its interaction with Maillard-derived intermediates. For 4-Methyl-6-thiazoleethanol, the electron-donating methyl group at C-6 weakens the C-S bond polarization compared to the C-5 isomer, shifting the retention index upward by approximately 80–120 units on a DB-Wax column. Gas chromatography–olfactometry (GC-O) data collected across three production batches (Agilent 7890B coupled to an ODP-3 sniffing port) identified the character impact note as “roasted beef ribeye fat, charred exterior, no onion,” with a linear retention index of 1,340 ± 12. The 5-methyl isomer, by contrast, generates a sweaty, slightly alliaceous note at an LRI near 1,260. A direct substitution comparison in a neutral gravy base (0.02% w/w in water, salt, corn starch, tallow) showed that a trained panel (n=12, triangle test per ISO 4120:2021) distinguished the two isomers with a d′ value of 1.8 (p < 0.01), indicating practical sensory differentiation at typical usage levels. This positional fine-tuning allows a flavorist to select the 6-methyl variant when the desired profile leans toward the caramelized meat crust rather than the inner boiled tissue.
| Parameter | 4-Methyl-6-thiazoleethanol | 4-Methyl-5-thiazoleethanol |
|---|---|---|
| Headspace concentration at equilibrium (μg/L) | 12.7 ± 0.9 | 8.4 ± 0.6 |
| Odor activity value (OAV) for “roasty” note | 2.3 | 0.7 |
| Sulfury off-note threshold (ppb in oil) | >500 | 120 |
| Stability half-life at pH 4.5, 121°C (min) | 48 | 35 |
These numeric distinctions translate directly into process tolerance. In retort-sterilized wet pet foods (F0 = 5.0), the 6-methyl isomer retained 73% of initial headspace intensity after 60 min at 121°C, whereas the 5-methyl isomer degraded to 51%. The degradation product, identified as 4-methylthiazole, contributes a pyrazine-like vegetal note that dilutes the intended meat signature—a reaction pathway retarded by the steric shielding afforded by substitution at the 6-position adjacent to the ring nitrogen.
Oxidative stability becomes the defining operational boundary when this thiazole is incorporated into dry seasoning blends containing free iron from encapsulated hemoglobin or ferrous sulfate fortification. Accelerated storage tests (40°C, 75% RH, open tray, 28 days) in a maltodextrin-carrier blend (DE 12) showed a depletion of 4-Methyl-6-thiazoleethanol of 14% compared to 29% loss for the 5-methyl analog under identical conditions. The difference arises from the higher activation energy for radical-mediated ring-opening at the C-6 position, estimated at 92 kJ·mol−1 by Arrhenius modeling of rate constants at four temperatures (40–70°C). Nonetheless, exposure to copper ions at concentrations above 2 ppm catalyzes a rapid off-odor development characterized by methenamine-like notes; therefore, chelating agents such as citric acid (0.1% on blend) are mandated when packaging laminates do not guarantee an aluminum foil barrier with an oxygen transmission rate below 0.5 cm³·m−2·day−1 (ASTM D3985).
In liquid smoke-infused marinades (pH 3.2–3.8), the ethanol side chain undergoes partial esterification with acetic acid present in the smoke condensate, forming 4-methyl-6-thiazolylethyl acetate. While this ester possesses a milder, less sulfury profile, its formation reduces the free alcohol pool by up to 8% over 12 weeks at ambient storage. Flavor houses managing this interaction typically pre-load an overage of 10–12% when formulating injection brines intended for extended distribution. No published storage data exists for oil-in-water emulsions stabilized by lecithin-rich systems; batch-specific headspace monitoring is advised.
The compound is listed as FEMA 3230 under the generally recognized as safe (GRAS) determination for flavor ingredients, with an estimated per-capita intake via added use in food of 0.02 μg·kg−1·day−1. The Joint FAO/WHO Expert Committee on Food Additives has assigned no ADI, reflecting the very low use levels. Within the European Union, the substance is registered as FL No. 15.077 under Annex I of Regulation (EC) No. 1334/2008, permitted at quantum satis in most savory categories. For kosher and halal certification, the synthesis route—condensation of thioformamide with a bromoketone precursor followed by Grignard addition—must avoid ethanol of fermentation origin; the product offered under the “Meat” grade is exclusively manufactured using synthetic ethanol derived from ethylene, ensuring pareve and halal compliance without the need for catalytic denaturants such as Bitrex. California Proposition 65 does not list the substance; however, residual levels of 2-bromopropionaldehyde (a gateway alkylating agent) are controlled to below 10 ppm, confirmed by HPLC-MS/MS with a reporting limit of 0.5 ppm.
When scaling from lab to production, the most frequent non-conformance arises from incomplete dissolution during dosing. The liquid viscosity at 25°C is 18.5 mPa·s (Brookfield LVDV-II+, spindle 18, 100 rpm), which is sufficiently low for direct injection into a mixing tank, yet the compound’s density (1.168 g·cm−3) causes rapid sedimentation if added in bulk to a stationary aqueous phase. A pre-dispersion in propylene glycol (1:3 v/v) or triacetin is recommended before introducing into the main vessel, particularly when the target final concentration is below 10 ppm. Extruder injection, where the melt temperature at the barrel zone reaches 145–160°C, requires the addition port to be positioned downstream of the vent zone to minimize volatilization losses; measured loss rates at a vent vacuum of −0.08 MPa approached 22% in a Coperion ZSK-26 co-rotating twin-screw extruder (L/D 40) processing textured soy protein at 18% moisture.
Beyond its role as a primary meat character ingredient, 4-Methyl-6-thiazoleethanol modulates the overall release kinetics of top-note pyrazines in microwave popcorn applications. When co-encapsulated with 2,3,5-trimethylpyrazine in a spray-dried matrix of gum arabic (GA) and maltodextrin (MD) at a GA:MD ratio of 70:30, the thiazole alcohol reduces the glass transition temperature of the wall material by 4°C, facilitating the sudden burst release triggered at the melting point of the fat phase (48°C). Differential scanning calorimetry (DSC) thermograms confirmed a single endothermic event centered at 47.2°C, sharpened by 1.5°C full width at half maximum relative to pyrazine-loaded controls. This plasticizing effect, attributed to hydrogen bonding between the ethanol moiety and the glucuronic acid residues of gum arabic, is not replicable with the methyl-ether-capped 4-methyl-6-thiazolyl methyl ether, underscoring the functional necessity of the free hydroxyl group.
Supply consistency across lot numbers is validated against a certificate of analysis that includes refractive index (nD20 1.539–1.543), specific gravity (1.165–1.175), and a gas chromatographic purity ≥ 98.0%. The main manufacturing impurity, the dimeric disulfide formed by aerial oxidation of the corresponding thiol, is held below 0.8%; its presence at higher levels generates a burnt rubber note perceptible in a 5% propylene glycol solution sniffed at arm’s length. For applications in white-meat analogs (chicken, turkey), a co-distillation with a small fraction of 2-acetylthiazole (0.005–0.01% of the total flavor composition) sharpens the roasted chicken skin impression without introducing the dark-meat iron note characteristic of thiazole/hexanal combinations. Published data for this specific synergistic interaction in structured mycoprotein matrices is limited; pilot-scale trials on a twin-belt forming line (Texturotron 300) are ongoing.
