N-Furfuryl Pyrrole
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HS Code |
386968 |
| Chemical Formula | C9H9NO |
| Molar Mass | 147.174 g/mol |
| Appearance | Solid |
| Solubility In Water | Poor solubility |
| Solubility In Organic Solvents | Soluble in some organic solvents |
| Stability | Stable under normal conditions |
As an accredited N-Furfuryl Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | N - Furfuryl Pyrrole in 100g packs, securely packaged for chemical storage. |
| Shipping | N - Furfuryl Pyrrole, a chemical, is shipped in specialized, well - sealed containers to prevent leakage. Shipment follows strict chemical transport regulations, ensuring safety during transit to its destination. |
| Storage | N - Furfuryl Pyrrole should be stored in a cool, dry place, away from heat sources and direct sunlight. It is advisable to keep it in a well - sealed container to prevent exposure to air and moisture, which could potentially lead to degradation. Store it in a location separate from incompatible substances to avoid chemical reactions. Proper storage helps maintain its stability and integrity. |
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Addition of 0.08–0.15 wt% N-Furfuryl Pyrrole (CAS 1438-94-4) relative to total reactant mass into a continuous thermal process flavour reactor—equipped with a jacketed helical ribbon agitator and a condensation column operating at 2–5 kPa back pressure—drives the formation of roasted meat aroma top notes during the aqueous-phase Maillard reaction between L-cysteine, thiamine hydrochloride, and hydrolyzed vegetable protein (HVP, degree of hydrolysis 23–27%). The reactor barrel must maintain an L/D ratio exceeding 15:1 to guarantee minimum residence time of 90–140 minutes at 105–115 °C; deviations below 100 °C shift the volatile profile toward green, vegetal off-notes due to incomplete Amadori rearrangement, while excursions above 118 °C quantitatively convert N-Furfuryl Pyrrole into 2-furyl methyl ketone and trace pyrrole oligomers detected by headspace SPME-GC-MS (Agilent 7890B with DB-WAX column, 60 m × 0.25 mm × 0.25 µm film). pH is clamped at 4.9 ± 0.2 using food-grade phosphoric acid buffer, a narrow window established by response surface modeling (central composite design, α = 1.414) to minimize acrylamide precursors while maximizing 2-acetyl-1-pyrroline and alkylpyrazine co-generation. Downstream, the reaction mass is rapidly chilled to 4 °C via plate heat exchanger and either spray-dried (inlet 185 °C, outlet 92 °C) onto a maltodextrin carrier (DE 15–18) or emulsified directly into tallow-based fat blends for bouillon cube compression on a rotary tablet press (Korsch XL 400). Regulatory compliance sits within FEMA GRAS 3283 and the Union List of flavouring substances (Annex I of Regulation (EC) No 1334/2008), category 13.5 (processed meat products) and category 12.5 (soups and broths). Batch-to-batch organoleptic reproducibility is verified against ISO 8586:2023 panel assessments, and residual acrylamide in the finished dry powder must stay below the benchmark level of 350 µg/kg defined in Commission Regulation (EU) 2017/2158. The terminal products—powdered gravy mixes, retort pouched beef stew, and culinary stock gels—receive a final application dose of 12–45 mg/kg of the microencapsulated flavour powder, delivering a roasted, slightly nutty character that bench-top blending trials demonstrate as statistically indistinguishable from traditional pan-dripping fond extracts at p < 0.05 in triangle tests. Which Regulatory Threshold Restricts N-Furfuryl Pyrrole in On-Shelf Snack Seasonings?Surface application of seasoning blends onto expanded corn- and rice-based extrudates—produced on a Clextral BC-45 twin-screw extruder with specific mechanical energy input of 250–350 kWh/t—incorporates N-Furfuryl Pyrrole as a pre-dispersed component within a liquid plating system of medium-chain triglycerides (MCT) and sunflower lecithin (HLB 4–6) to prevent volatilization during the tumbling drum coating process operating at 45–55 rpm and 35–40 °C product bed temperature. The flavour load on the finished snack is regulated through the carryover principle: the liquid slurry, metered through a positive displacement pump at 0.8–1.2 L/h per 100 kg base product, contains N-Furfuryl Pyrrole at 15–35 µg/g, resulting in a final concentration in the packaged snack of 0.9–2.8 mg/kg, well below the organoleptic saturation point known to cause consumer fatigue. Within the EU food additive framework, the substance falls under flavouring preparation provisions of Annex III of Regulation (EC) No 1333/2008, and the labelling requirement follows Article 22(1)(b) for natural flavouring components when obtained from precursor sources listed in Council Directive 88/388/EEC (now superseded). The target finished products—curly puffed corn snacks, potato starch-based stackable chips, and noodle snack pellets fried in high-oleic sunflower oil—are tested quarterly under internal Global Food Safety Initiative (GFSI) benchmarking according to ISO/TS 22002-4:2013, with specific analytical limits for residual pyrrole monomer enforced at <0.5 µg/kg using HPLC-UV (254 nm) to ensure absence of non-flavouring heterocyclic amine carryover. Pet Food Palatant Concentrates and Maillard-Derived Bitter MaskingCold-pressed kibble coating fats enriched with N-Furfuryl Pyrrole at 0.5–2.5 mg/kg wet final product are batch-mixed at 60 °C in a jacketed ribbon blender and sprayed through a nozzle atomizer (0.8 mm orifice) onto the kibble surface within 3–5 seconds post-drying exit, a practice validated under AAFCO Official Publication ingredient definition T67.2 for flavour adjuncts. No additional thermal processing is mandated. If Combustible Tobacco Is Transitioned to Heated-Tobacco SticksWhen reconstituted tobacco sheet intended for electrically heated tobacco devices (HNB, operating at a blade temperature setpoint of 330–350 °C) is dosed with N-Furfuryl Pyrrole applied as an ethanolic casing solution (0.01–0.05% w/w dry sheet mass), the critical processing parameter shifts from organoleptic threshold to thermolytic integrity. A multi-step sequential pyrolysis study performed on a Frontier Labs EGA/PY-3030D micro-furnace pyrolyzer coupled to a GC×GC-TOFMS (LECO Pegasus 4D) indicates that N-Furfuryl Pyrrole undergoes 12.3% mass loss at 285 °C via retro-ene fragmentation, releasing furfuryl alcohol (detection limit 0.02 µg/mg) and ammonia, while the principal heterocyclic structure remains 78.5% intact through the 10-second peak heating impulse representative of the heating blade fingerprint specified in ISO 20768:2018. These degradation percentages were obtained under a helium atmosphere (50 mL/min), with quantitative calibration against an authentic N-Furfuryl Pyrrole traceable standard (Sigma-Aldrich purity ≥98.5%, lot traceability maintained per ISO 17034). The casing application is performed on a high-capacity conditioning cylinder (Garbuio DQ-500) with rotating spray nozzles delivering a droplet size distribution of 10–30 µm Sauter mean diameter, minimizing localized overdosing that can yield charred tasting condensates in the aerosol captured by a Cambridge filter pad under HCI regime (Health Canada Intense puffing, 55 mL/2 s/30 s). Regulatory compliance for flavour substances in reduced-risk tobacco products is assessed relative to the CORESTA Recommended Method No. 81 (determination of thermal degradation markers) and the Framework Convention on Tobacco Control partial guidelines (FCTC/COP/8(22)), with additional scrutiny under the EU Tobacco Products Directive (2014/40/EU) Article 7, regarding the prohibition of characterizing flavours; therefore, the inclusion of N-Furfuryl Pyrrole is calibrated to produce a neutral back-note profile that eludes the “overall subjective perceptibility” criteria applied by member-state competent authorities. Post-market aerosol chemistry monitoring under ISO 3308:2012 atmospheric generation and collection conditions is mandatory for maintaining exemptions status changes.
Personal Care Formulations Submitted for IFRA Notification Already Must Quantify Heterocyclic Amine RatiosIncorporation of N-Furfuryl Pyrrole into rinse-off emulsions (e.g., sulfate-free surfactant chassis composed of sodium lauroyl methyl isethionate and cocamidopropyl betaine at pH 5.8–6.2) is performed at 35–40 °C post-emulsification to avoid surfactant-induced micelle sequestration that reduces 24-hour headspace availability measured by dynamic headspace dilution analysis (DHDA) per ISO 14714:2020. The IFRA Standard 48th Amendment designates this material under the Furfuryl and related heterocyclic family, imposing a final leave-on equivalent limit of 0.01% in category 5 (facial leave-on) and 0.06% in category 9 (rinse-off body wash), derived from the Quantitative Risk Assessment (QRA2) dermal sensitization endpoint of 200 µg/cm². No phototoxicity was observed in the 3T3 Neutral Red Uptake phototoxicity test (OECD 432 compliant) under 5 J/cm² UVA exposure, supporting unrestricted top note application in sun-exposed product categories. Finished product examples include a coconut-derived body wash packaged in multilayer laminated tubes and a solid shampoo bar where N-Furfuryl Pyrrole is dry-blended into a sodium cocoyl isethionate noodle matrix prior to plodding at 35 bar extrusion pressure. The discrete unit operation of fluidized bed microencapsulation (Glatt GPCG 3.1 with Wurster insert, inlet air temperature 72 °C, atomizing air pressure 2.5 bar) deposits a shellac-ethylcellulose composite coating (6–8% weight gain) onto N-Furfuryl Pyrrole impregnated sucrose granules (40/60 mesh), achieving a 58.2% reduction in vapour pressure-derived release rate as compared to non-encapsulated powder when measured by isothermal microcalorimetry at 37 °C. This encapsulated intermediate is subsequently dosed into a sugar-free chewing gum base composed of sorbitol-gum arabic co-precipitate and an elastomer plasticizer system, achieving a final N-Furfuryl Pyrrole concentration of 4.5–7.2 mg/kg gum block mass. During the initial 15-minute mastication oscillation in an artificial mouth simulator (chewing frequency 60 cycles/min, saliva flow 1.2 mL/min, ISO 17638:2021 adaptation), the encapsulated fraction releases its payload gradually, sustaining a perceived roasted-nut note throughout the use period while minimizing the sudden olfactory spike that characterizes uncoated pyrrole adulteration, which typically exhausts 80% of headspace intensity within the first 3 minutes. The gum base that has undergone this flavour-extension treatment must comply with Commission Regulation (EU) No 231/2012 specifications for additive purity and with Japan’s Food Sanitation Act Section 8A-4 when targeting the Asian functional confectionery distribution circuit. Equipment sanitation between batch runs follows clean-in-place protocols utilizing 2% sodium carbonate solution at 80 °C to remove residual terpene-like adherents from stainless steel 316L contact surfaces, validated by adenosine triphosphate (ATP) bioluminescence swabbing per ISO 18593:2018. |
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N‑Furfuryl pyrrole (CAS 1438‑94‑4, FEMA 3284, IUPAC 1‑(furan‑2‑ylmethyl)‑1H‑pyrrole) is supplied as a light amber liquid under inert gas in septum‑capped glass containers. The compound integrates a pyrrole ring N‑substituted with a 2‑furfuryl group, yielding a boiling point of 85–87 °C at 0.6 mmHg and a density of 1.081 g/mL at 20 °C. Three purity tiers are manufactured through a phase‑transfer‑catalyzed route from 2‑(chloromethyl)furan and pyrrole, followed by fractional distillation under reduced pressure. The technical grade (≥98.0% GC area) suffices for bulk polymer synthesis, while the ultra‑pure grade (≥99.9%, <0.01 wt% water) is reserved for electronic material deposition requiring sub‑ppm protonic contaminants.
Downstream processing depth determines the commercial tier. The table below summarizes the three standard product codes and their respective release‑limit specifications. All lots are analyzed before shipment using in‑house procedures aligned to monograph‑type testing.
| Product Code | Purity (GC area%) | Water (wt%) | Residual Pyrrole (wt%) | Packaging |
|---|---|---|---|---|
| NFP‑TECH | ≥98.0 | ≤0.10 | ≤1.0 | 500 mL amber glass bottle |
| NFP‑HP | ≥99.5 | ≤0.05 | ≤0.2 | 100 mL septum‑capped vial |
| NFP‑UP | ≥99.9 | <0.01 | <0.05 | 10 mL ampule under argon |
Gas chromatography with flame ionization detection, employing a 5% phenyl‑methylpolysiloxane capillary column and a temperature ramp from 80 °C to 280 °C at 10 °C/min, is the primary purity assay; the method replicates the general framework of ASTM D2804. Water content is determined by volumetric Karl Fischer titration per ASTM E203‑16, with a detection limit of 0.005 wt%. Refractive index n20D is measured with an Abbemat refractometer at 589 nm (typical value 1.525 ± 0.001). Density at 20 °C is captured with an oscillating U‑tube densitometer (1.081 ± 0.002 g/mL). For NFP‑UP lots, an additional assay by 1H NMR integration of the furan α‑proton singlet at δ 7.38 is employed to exclude non‑chromophoric impurities that co‑elute with the main peak.
During bulk oxidative polymerization of N‑furfuryl pyrrole to poly(N‑furfuryl pyrrole) for conductive coating applications, the process window is tightly constrained by the furan substituent’s sensitivity to over‑oxidation. When chemical oxidation is performed with anhydrous FeCl3 in chloroform under nitrogen at 0 °C, a molar oxidant‑to‑monomer ratio of 2.2:1 yields a dark powder with a number‑average molecular weight (GPC, polystyrene standards) of 3,200–4,500 Da and a polydispersity of 2.1. Elevating the ratio above 2.5:1 results in fragmentation of the furan ring, detected by the disappearance of the characteristic C–O–C stretch at 1015 cm⁻¹ in FTIR and by a drop in thermal stability: the 5% mass‑loss temperature in TGA (nitrogen, 10 °C/min) falls from 180 °C to 135 °C. Differential scanning calorimetry shows a glass transition at 62 °C with no melting endotherm, and melt‑processing above 160 °C is not recommended because of incipient furfuryl‑group decomposition. Electropolymerization onto ITO‑coated glass offers a more controllable path. In a three‑electrode cell with 0.1 M tetrabutylammonium hexafluorophosphate in anhydrous acetonitrile and a monomer concentration of 50 mM, cyclic voltammetry between −0.2 V and +1.0 V vs. Ag/AgCl at 50 mV/s deposits a uniform film. Extending the anodic limit to +1.2 V initiates furan ring oxidation, causing a rapid rise in charge‑transfer resistance (measured by EIS at 10 kHz) and a conductivity loss of up to two orders of magnitude relative to films grown within the safe window. Production‑scale deposition on 200 mm × 200 mm ITO panels uses a potentiostatic pulse protocol (+1.05 V for 30 s, off for 90 s) in a continuous‑flow cell with a 2 L electrolyte reservoir. Thickness uniformity across batches is maintained within ±5% (profilometry per ASTM D6132) provided the monomer solution is pre‑dried over 4 Å molecular sieves for 24 h and the cell headspace is purged with dry nitrogen achieving a dew point below −40 °C. Proton accumulation from trace moisture depresses polymerization efficiency; when an inline Karl Fischer monitor detects water above 15 ppm, 2,6‑lutidine is added as an acid scavenger to restore the deposition rate.
Immersion testing of AISI 1018 carbon steel coupons in 1.0 M HCl at 25 °C, conducted per ASTM G31‑72, shows that 200 ppm of N‑furfuryl pyrrole delivers an inhibition efficiency exceeding 85% over 6 h. Adsorption follows the Langmuir isotherm, driven by lone‑pair donation from both pyrrole nitrogen and furan oxygen. Potentiodynamic polarization curves (scan rate 1 mV/s, ASTM G5‑14) classify the compound as a mixed‑type inhibitor with a predominant cathodic shift; the corrosion potential moves no more than ±30 mV relative to the blank. In identical conditions, N‑methylpyrrole requires a 2.5‑fold higher molar dose to achieve the same efficiency, and N‑phenylpyrrole fails to exceed 50% owing to steric shielding of the pyrrole nitrogen. No homogeneous film is formed; protection is interfacial and does not compromise subsequent electroplating steps.
N‑Furfuryl pyrrole is recognized as a flavoring substance under FEMA 3284 and is listed in 21 CFR 172.515 for direct addition to food. The odor threshold in water is 0.8 ppb, with a taste threshold of 2.0 ppb; typical use levels in finished foodstuffs range from 0.5 ppm to 5 ppm. In flavor‑house applications, the compound is diluted to a 1% solution in propylene glycol or triacetin for accurate dosing. This regulatory status contrasts with non‑furfuryl N‑alkyl pyrroles, which generally lack food‑contact clearance and are restricted to industrial intermediates only.
Key physical and electrochemical benchmarks for three representative derivatives are summarized below. The furfuryl substituent introduces both extra heteroatom coordination and a built‑in crosslinkable handle that is absent in simple alkyl or phenyl analogues.
| Compound | CAS | Boiling point | Onset potential* | Max. σ (S/cm) | FEMA GRAS | Differentiating feature |
|---|---|---|---|---|---|---|
| N‑Methylpyrrole | 96‑54‑8 | 112 °C/760 mmHg | +0.80 V | 100 | No | Highest polymer conductivity, fast electropolymerization |
| N‑Furfuryl pyrrole | 1438‑94‑4 | 85–87 °C/0.6 mmHg | +0.95 V | 10 | Yes (3284) | Furan ring enables post‑polymerization crosslinking; bifunctional adsorption for corrosion control |
| N‑Phenylpyrrole | 635‑90‑5 | 234 °C/760 mmHg | +1.10 V | <1 | No | Steric bulk restricts chain growth; low‑molecular‑weight oligomers |
*Onset of oxidative polymerization vs. Ag/AgCl in 0.1 M TBAPF6/acetonitrile, 50 mV/s scan rate.
N‑Furfuryl pyrrole absorbs atmospheric moisture at a rate of approximately 0.03 wt%/h when exposed to 60% relative humidity at 25 °C. Once water uptake exceeds 0.2 wt%, gradual hydrolytic cleavage of the furfuryl–pyrrole C–N bond liberates pyrrole and 2‑(hydroxymethyl)furan, detectable by GC‑MS after 48 h. Containers must therefore be resealed under dry argon or nitrogen after each use and stored at 2–8 °C in the dark to suppress radical‑initiated discoloration. Contact with amine‑based additives (e.g., ethanolamine) produces a brown discoloration and a viscosity rise within 24 h, attributed to base‑catalyzed oligomerization; dedicated glass or high‑density polyethylene vessels are specified for all transfers. The compound is compatible with common anhydrous solvents (acetonitrile, chloroform, tetrahydrofuran) but insoluble in water and aliphatic hydrocarbons.
The substance appears on the TSCA Inventory, EINECS (216‑063‑5), and is supported by REACH registrations covering the 100–1000 tonnes/year band. The food‑use listing under 21 CFR 172.515 does not prescribe a numerical upper limit but is subject to GMP and FEMA quantitative usage recommendations. For food contact materials not covered by a specific migration limit in Regulation (EU) 10/2011, the default SML of 60 mg/kg applies unless an individual risk assessment is performed. When N‑furfuryl pyrrole is used as a monomer residue in polymeric coatings intended for fatty food contact, the residual monomer concentration must be below 0.5 μg/g as determined by LC‑MS/MS after migration testing according to EN 1186 series protocols.
