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Syringol

Syringol, systematically named 2,6-dimethoxyphenol, is an organic compound with the molecular formula C₈H₁₀O₃ and a molecular weight of 154.16 g/mol.^[1] It belongs to the class of phenolic compounds, characterized by a benzene ring substituted with a hydroxyl group and two methoxy groups at the 2 and 6 positions, and is identified by the CAS Registry Number 91-10-1.^[1] Syringol is primarily produced through the pyrolysis of lignin, a polyphenolic polymer abundant in plant cell walls, making it a prominent volatile component in wood smoke, charcoal emissions, and the aroma of smoked or grilled foods.^[2] It can also be derived from the reduction of syringaldehyde or isolated from natural sources such as dichloromethane extracts of mangrove plants (e.g., twigs, leaves, and bark) and the pericarp of Areca catechu.^[1]^[3] In industrial applications, syringol serves as a key ingredient in synthetic smoke flavorings due to its intensely smoky and phenolic scent, enhancing the taste profile of processed meats and other grilled products.^[2] It is employed in perfumery to impart authentic wood-smoke notes and in the cosmetics industry for its potential in formulations targeting oxidative stress.^[1] Furthermore, syringol plays a role in biotechnological processes, such as microbial engineering for lignin valorization using bacteria like Pseudomonas putida KT2440.^[1] Biologically, syringol demonstrates antioxidant activity, effectively scavenging DPPH free radicals with an EC₅₀ of 41.8 μM, alongside anti-inflammatory and antihyperglycemic effects that suggest therapeutic potential in oxidative stress-related disorders.^[1] It is not classified as a skin sensitizer, supporting its safety in topical applications.^[1] Derivatives, such as MHY884, have been investigated for inhibiting melanin synthesis by mitigating oxidative damage, highlighting syringol's relevance in pharmaceutical research for skin health and beyond.^[1]

Chemical Structure and Properties

Nomenclature and Molecular Formula

Syringol is the common name for the organic compound with the systematic IUPAC name 2,6-dimethoxyphenol.^[4] This nomenclature reflects its structure as a phenol derivative with methoxy substituents at the ortho positions relative to the hydroxyl group.^[4] Other recognized synonyms include pyrogallol 1,3-dimethyl ether and 2-hydroxy-1,3-dimethoxybenzene.^[4]^[1] The molecular formula of syringol is C₈H₁₀O₃, corresponding to a molecular weight of 154.16 g/mol.^[4] Structurally, it features a benzene ring with a hydroxyl group attached at position 1 and two methoxy groups (-OCH₃) at positions 2 and 6, making it a symmetric ortho-dimethoxyphenol.^[4] The compound is identified by the CAS Registry Number 91-10-1.^[4] The etymology of "syringol" traces back to "syringa," the genus name for the lilac plant (Syringa vulgaris), owing to its structural similarity to syringin—a glycoside isolated from lilac bark—and its connection to syringaldehyde, a derivative of lignin.^[2] In the context of lignin chemistry, syringol originates from the sinapyl alcohol monomer unit that forms the syringyl (S) component of hardwood lignins.^[5]

Physical Characteristics

Syringol appears as a white to off-white crystalline powder or solid, though commercial samples may exhibit a tan coloration due to minor impurities or oxidation.^[6] It has a molecular weight of 154.16 g/mol. The compound melts at 50–57 °C and boils at 261 °C under standard atmospheric pressure.^[8] Its flash point is 140 °C (284 °F). The density of solid syringol is approximately 1.17 g/cm³, based on structural estimates.^[8] Syringol is moderately soluble in water, with solubility around 20 g/L at 20 °C, and exhibits high solubility in organic solvents such as ethanol and ether.^[4]^[8] It possesses an intensely smoky, phenolic odor reminiscent of wood smoke or grilled meat.^[10]^[4] Under standard conditions, syringol is stable but sensitive to oxidation by air and light, which can lead to discoloration over time.^[11]

Chemical Reactivity

Syringol, as a phenolic compound, exhibits characteristic acidity due to its hydroxyl group, with a pKa value of approximately 9.97, enabling deprotonation to form a phenolate ion under mildly basic conditions.^[8] This acidity facilitates its role in hydrogen bonding and salt formation, influencing its reactivity in aqueous environments. The compound readily undergoes one-electron oxidation, forming stable radical intermediates, which is leveraged in peroxidase assays such as those employing horseradish peroxidase.^[12] In enzymatic systems, this process follows the equation:

\text{C}_8\text{H}_{10}\text{O}_3 \rightarrow \text{radical intermediate} + \text{H}^+ + \text{e}^-

This oxidation highlights syringol's utility as a substrate for measuring peroxidase activity.^[13] Additionally, its antioxidant properties stem from the phenolic OH group, which scavenges free radicals effectively, with a reported EC₅₀ of 41.8 μM in DPPH assays.^[1] In electrophilic aromatic substitution reactions, the hydroxyl group acts as the dominant ortho/para director, overshadowing the directing effects of the methoxy groups at positions 2 and 6, though these substituents enhance overall ring activation.^[14] The methoxy groups remain stable under neutral conditions but can undergo cleavage via acidic or basic hydrolysis, yielding catechol derivatives and methanol.^[15] Thermally, syringol demonstrates stability up to approximately 250 °C, beyond which decomposition occurs, producing volatile products relevant to pyrolysis processes.^[16]

Occurrence and Production

Natural Sources

Syringol, also known as 2,6-dimethoxyphenol, occurs naturally as a minor phenolic component in select plant species, notably the roots of Panax japonicus var. major (Japanese ginseng) and Mucuna birdwoodiana. In Panax japonicus, it has been identified among bioactive constituents extracted from root tissues, contributing to the plant's chemical profile. Similarly, in Mucuna birdwoodiana, syringol appears as part of the phenolic fraction in vegetative parts, as documented in studies on prostaglandin inhibitors from this legume. It has also been isolated from dichloromethane extracts of mangrove plants (such as twigs, leaves, and bark) and from the seeds of Areca catechu.^[1]^[17] These occurrences highlight syringol's role as a trace natural product in specific botanical sources, often alongside other methoxyphenols. Within plant structural components, syringol is derived from syringyl (S) units in lignin, which originate from the polymerization of sinapyl alcohol monomers. These S units predominate in the lignins of angiosperm hardwoods, such as oak and birch, where they can constitute a significant portion of the aromatic polymer, facilitating greater structural diversity compared to the guaiacyl (G)-dominant lignins in gymnosperm softwoods like pine. The higher prevalence of S units in angiosperms versus gymnosperms underscores syringol's association with evolutionary adaptations in flowering plants' vascular tissues. This compositional difference is reflected in the syringyl/guaiacyl (S/G) ratio, a key metric for lignin characterization. Environmentally, syringol appears in trace quantities within natural matrices such as beechwood tar creosote, soil organic matter, and phenolic mixtures arising from biomass decay. In decaying plant material, microbial processing of lignin releases syringol-like compounds, integrating them into soil humus as part of broader organic matter formation. Concentrations in plant extracts generally remain low, though elevated levels have been noted in specialized tissues like ginseng roots and certain barks, where it forms part of the extractable fraction. Its detection in natural samples typically involves gas chromatography-mass spectrometry (GC-MS) analysis of floral, woody, or root extracts, enabling identification through characteristic mass spectra and retention times.

Biosynthetic and Pyrolysis Pathways

Syringyl units, the precursors to syringol in lignin, are biosynthesized in plants through the phenylpropanoid pathway, beginning with the conversion of L-phenylalanine to p-coumaryl alcohol, followed by successive hydroxylation and methylation steps to form sinapyl alcohol.^[18] This monolignol, sinapyl alcohol, is then transported to the cell wall where it undergoes oxidative polymerization via peroxidases and laccases, incorporating syringyl (S) units into the lignin polymer, particularly in angiosperms.^[18] The process is regulated by transcription factors such as NST1/SND1, which directly activate genes like ferulic acid 5-hydroxylase (F5H) essential for the 5-hydroxylation leading to sinapyl alcohol.^[18] Syringol itself arises from minor degradation of these syringyl lignin units, often through oxidative or reductive depolymerization processes in plant tissues or by microbial activity, though such natural yields are low.^[19] In pyrolysis pathways, syringol is produced via thermal decomposition of lignin, primarily from the cleavage of syringyl units in hardwood lignin at temperatures of 400–600 °C, where primary reactions depolymerize β-ether linkages to release 4-substituted syringols, followed by secondary demethoxylation and methylation.^[20] Yields of syringol reach up to 5–10% by weight from hardwood lignin under optimized fast pyrolysis conditions, contributing to bio-oil fractions alongside other phenols.^[21] A simplified representation of the pyrolysis reaction for a syringyl unit is:

\text{Lignin (syringyl unit)} \xrightarrow{400-600^\circ \text{C}} \text{syringol} + \text{other volatiles}

^[20] Industrial production of syringol often employs catalytic depolymerization of lignin, such as oxidative processes using mixed metal oxide catalysts like Cu-Fe/Al₂O₃ in alkaline NaOH conditions with H₂O₂ under microwave heating, achieving a syringol yield of 27 wt% from NaOH-extracted lignin with 55% selectivity.^[22] In laboratory settings, syringol is synthesized by reducing syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) to convert the aldehyde group to a methyl group, commonly via Wolff-Kishner reduction with hydrazine and base or Clemmensen reduction with Zn(Hg)/HCl. Yields in both pyrolysis and catalytic depolymerization are influenced by factors including temperature (higher temperatures favor demethoxylation but reduce monomer selectivity), catalyst type (e.g., metal oxides enhance C-O bond cleavage), and the lignin's S/G ratio (higher syringyl content increases syringol output due to more labile S units).^[20]^[22]

Analytical Role in Lignin

Syringyl/Guaiacyl Ratio

The syringyl/guaiacyl (S/G) ratio quantifies the relative abundance of syringyl (S) units, derived from sinapyl alcohol, to guaiacyl (G) units, derived from coniferyl alcohol, within the lignin polymer of plant cell walls. This ratio serves as a key indicator of lignin composition and source, with values typically ranging from 0.5 to 2.5 in hardwoods (angiosperms) and 0 to 0.3 in softwoods (gymnosperms), reflecting the predominance of G units in coniferous species and a more balanced S and G contribution in deciduous ones.^[23]^[24]^[25] In relation to syringol, the S/G ratio directly influences pyrolysis products, as thermal degradation of S units primarily yields syringol and its derivatives, while G units produce guaiacol; consequently, higher S/G ratios in lignins correlate with elevated syringol levels in wood smoke emissions from hardwoods compared to softwoods. Biologically, the S/G ratio modulates lignin's structural properties, with higher S content leading to less condensed networks that reduce overall rigidity and enhance cell wall flexibility, aiding digestibility in herbivores and facilitating the evolution of efficient water-conducting vessels in angiosperms. This compositional shift from G-dominant lignin in gymnosperms to S-enriched forms in angiosperms underscores an adaptive progression in vascular plant development for optimized hydraulic efficiency.^[26]^[27]^[28] The S/G ratio also bears significant implications for industrial processing, where elevated values (>1) facilitate delignification in pulp production by promoting easier lignin removal due to fewer cross-links, a trait exploited in forestry and kraft pulping for hardwood classification and optimization. In biofuel conversion, high S/G lignins aid initial biomass saccharification and facilitate downstream lignin valorization due to the additional methoxy groups on S units, which decrease thermal stability and promote depolymerization pathways.^[29]^[24]^[30] Historically, the S/G ratio was first systematically quantified in the 1980s through thioacidolysis, a degradative method developed by Lapierre and Rolando that cleaves lignin ether bonds to release quantifiable monomers, enabling precise structural analysis.^[31]

Characterization Methods

Syringol, a key syringyl unit derivative in lignin, is characterized primarily through analytical techniques that detect and quantify it alongside guaiacyl units to determine the syringyl/guaiacyl (S/G) ratio in biomass samples. These methods are essential for assessing lignin composition without extensive sample preparation, focusing on thermal, spectroscopic, and chemical degradation approaches. Pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) serves as a standard high-throughput technique, while nuclear magnetic resonance (NMR) spectroscopy, thioacidolysis, and Fourier-transform infrared (FTIR) spectroscopy provide complementary insights into structural features.^[23] Pyrolysis-GC/MS involves heating lignocellulosic samples to 500 °C for approximately 30 seconds in an inert atmosphere, which thermally degrades lignin into volatile phenolic fragments, including syringol and guaiacol derivatives, that are then separated by gas chromatography and identified by mass spectrometry. Key syringyl markers appear as ions at m/z 154, 167, 181, 194, 208, and 210, while guaiacyl markers include m/z 120, 124, 137, 138, 164, and 178; the S/G ratio is calculated from the integrated peak areas of these respective groups. This method is particularly effective for rapid screening of biomass feedstocks, though it may slightly overestimate syringyl content due to the thermal lability of certain linkages.^[23]^[32] ¹³C NMR spectroscopy, often in solid-state cross-polarization magic-angle spinning (CP/MAS) mode, enables non-destructive analysis of lignin by resolving carbon signals associated with syringyl and guaiacyl units. The methoxy groups characteristic of syringyl units (two per unit) resonate at 55–60 ppm, allowing indirect estimation of the S/G ratio through integration relative to guaiacyl signals (one methoxy per unit) or aromatic carbons at approximately 146–153 ppm. Quantitative protocols use spectral widths of around 30,000 Hz and 45° pulse angles for precision within ±3% on larger samples, providing insights into overall methoxyl content per C9 lignin unit.^[33]^[34] Thioacidolysis followed by high-performance liquid chromatography (HPLC) quantifies non-condensed syringyl and guaiacyl monomers by selectively cleaving β-O-4 ether linkages in lignin. The process uses 2–5 mg of dry biomass treated with boron trifluoride diethyl etherate and ethanethiol in 1,4-dioxane at 100 °C for 4 hours, followed by neutralization, derivatization with BSTFA/TMCS, and analysis on a C18 column with a formic acid-acetonitrile gradient under multiple reaction monitoring. This yields thioethylated monomers for S and G units, offering high specificity for degradable lignin fractions.^[35]^[36] FTIR provides a rapid, non-destructive screening method for the S/G ratio by measuring absorbance intensities of characteristic bands in the 1700–900 cm⁻¹ region after spectral normalization at 1505 cm⁻¹. The syringyl units exhibit a prominent band at 1327 cm⁻¹ due to C=O stretching, while guaiacyl units show a band at 1267 cm⁻¹ attributed to C-O stretching; the ratio is derived from these relative intensities. This approach is suitable for comparative analysis across lignin types, such as hardwoods versus softwoods.^[37] Across these techniques, the S/G ratio is consistently computed as:

\text{S/G} = \frac{\sum \text{areas of S peak(s)}}{\sum \text{areas of G peak(s)}}

in resulting chromatograms or spectra, enabling standardized comparisons. These methods achieve sensitivity for syringol detection down to parts per million (ppm) levels in smoke-impacted or biomass-derived samples, supporting applications in environmental and biofuel research.^[23]^[38]

Applications

Food and Flavor Industry

Syringol functions as a primary volatile compound in liquid smoke flavorings, where it imparts essential smoky aromas to processed foods including grilled and smoked meats, fish, and cheeses.^[39] In these applications, syringol and its derivatives constitute a significant portion of the phenolic fraction responsible for the characteristic smoke flavor, comprising approximately 12% of the volatile components in some commercial products derived from hardwood pyrolysis.^[40] This compound is particularly valued for its role in replicating the sensory qualities of traditional smoking processes without the need for direct wood exposure, enabling consistent flavor delivery in industrial food production.^[41] In beverage applications, syringol is incorporated at concentrations up to 10 ppm in products such as whisky, rum, tea, and coffee to enhance phenolic and smoky notes.^[10] Its sensory profile is distinctly smoky, spicy, and phenolic, evoking associations with wood smoke, campfire, or bacon, with an odor detection threshold of approximately 13.3 ppb in air.^[42]^[43] At higher concentrations, it contributes to savory, nutty, and licorice-like undertones, broadening its utility in complex flavor blends.^[43] Syringol's use in the food industry is supported by its regulatory status: it is affirmed as Generally Recognized as Safe (GRAS) by the U.S. Food and Drug Administration under FEMA number 3137, and it is permitted in the European Union as a component of authorized smoke flavorings under Regulation (EC) No 2065/2003 for primary smoke condensates.^[42]^[44] Historically, syringol was identified in the early 1970s as a major constituent of hickory smoke extracts, with early studies isolating it from smoked meat brines and highlighting its prominence in phenolic profiles.^[45]^[46] In flavor formulations, syringol enhances the effects of guaiacol, another key phenolic, to achieve balanced smoky profiles; their combined presence amplifies perceptions of savory depth and overall smoke intensity in foods and beverages.^[47]^[48] Synthetic versions of syringol have increasingly replaced natural extracts since the late 20th century, offering greater consistency and purity in commercial liquid smoke products while minimizing variability from wood sources.^[40] This shift supports scalable production for the global food flavor market, where liquid smokes account for thousands of tons annually in the EU alone.^[44]

Chemical and Pharmaceutical Uses

Syringol serves as a valuable precursor in organic synthesis, notably for the production of syringaldehyde through targeted oxidation, often facilitated by engineered cytochrome P450 enzyme systems that convert the phenolic compound to its aldehydic derivative with high efficiency.^[49] This transformation leverages syringol's phenolic structure for applications in fine chemical production. Additionally, syringol derivatives are incorporated into azo dyes, where the methoxyphenol moiety enhances dye stability and color properties in textile formulations.^[50] Its inherent antioxidant capacity, stemming from free radical scavenging by the phenolic hydroxyl group, further positions syringol in the development of stabilizers and protective agents against oxidative degradation.^[51] In polymer chemistry, syringol undergoes epoxidation to yield multi-functional tri-epoxides, which serve as building blocks for lignin-derived resins; these enhance the flexibility and mechanical performance of bio-based polymers through two-step synthetic routes that achieve yields up to 80%.^[52] The process exploits syringol's reactivity toward epoxide formation, enabling customizable thermoset materials with improved processability for sustainable composites. Its phenolic reactivity, as detailed in chemical reactivity studies, underpins this efficient epoxidation without requiring harsh conditions. Pharmaceutically, syringol exhibits anti-inflammatory effects by down-regulating key enzymes such as COX-2, cPLA2, and 5-LOX at micromolar concentrations (10–100 μM), thereby reducing pro-inflammatory mediator production in models of paw edema.^[53] This inhibition occurs independently of substrate or calcium ion levels, suggesting direct enzyme interaction. Syringol also demonstrates antifungal potential, with extracts rich in the compound showing minimum inhibitory concentrations (MIC) of 0.78 mg/mL against Aspergillus species, attributed to disruption of fungal growth pathways.^[54] In biofuel processing, hydrodeoxygenation (HDO) of syringol to phenol employs iron-mediated catalysts like CoFeAg/SiO2, achieving 100% conversion and phenol selectivities up to 52.4% under moderate conditions, supporting sustainable production of aromatic platform chemicals from lignin-derived feedstocks.^[55] For perfumery, syringol imparts a characteristic smoky top note to compositions evoking leather, tobacco, and incense, typically incorporated at 0.1–1% levels to add depth without overpowering other accords.^[56] Regarding toxicity, syringol displays low acute oral toxicity, with an LD50 exceeding 2000 mg/kg in mice, indicating minimal systemic risk at typical exposure levels; however, it can cause skin irritation upon direct contact, necessitating handling precautions.^[11]

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Fe-Mediated Enhancement of Phenol Selectivity in Syringol ...
Sep 8, 2025 · The hydrodeoxygenation of lignin-derived syringol to phenol faces challenges in selectively cleaving CAryl–O bonds while maintaining ...Missing: biofuel | Show results with:biofuel
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Exploring Syringol (2,6-Dimethoxyphenol) in Modern Perfumery
Nov 2, 2025 · In fragrance formulations, it can be used judiciously to add a sophisticated smoky layer to tobacco accords, enhance the ruggedness of leather ...