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2,6-dimethoxyphenol
2,6-dimethoxyphenol is a phenolic compound known for its smoky odor and medicinal flavor, used primarily as a flavor and fragrance agent.
General Material Description
2,6-dimethoxyphenol, also known as 1,3-dimethoxy-2-hydroxybenzene or syringol, is an organic compound classified among phenolic derivatives. It appears as a crystalline solid with a molecular formula of C8H10O3 and is characterized by a distinctive smoky and medicinal aroma. Its structure includes two methoxy groups and one hydroxyl group attached to a benzene ring, which contributes to its particular olfactory properties. 2,6-dimethoxyphenol is naturally found in materials such as beechwood tar creosote, dried bonito, coffee, maple syrup, hardwood smoke, and other products linked with partial wood combustion. The compound is used mainly as a flavor and fragrance agent thanks to its unique sensory profile. Further information and chemical specifics can be referenced via ChEBI.
Occurrence, Applicability & Potential Uses
This compound occurs naturally in diverse smoked and roasted products including beechwood tar creosote, dried bonito, coffee, maple syrup, hardwood smoke, tea, fire-cured tobacco, whiskey, and wine. Its presence is linked to processes involving thermal degradation or pyrolysis of lignin-containing materials. 2,6-dimethoxyphenol is employed primarily as a flavor and fragrance agent for imparting smoky and medicinal notes. It finds applications in products requiring smoky aromas such as smoked meat, bacon, smoked salmon, and nut flavorings. Regulatory bodies including FEMA (US) have reviewed its usage, assigning FEMA number 3137, confirming its acceptability within specified concentration limits for flavoring purposes.
Physico-Chemical Properties Summary
2,6-dimethoxyphenol is a solid at room temperature, melting between 54 and 57°C and boiling near 260 to 261°C at standard atmospheric pressure. The compound has moderate volatility with a vapor pressure of 0.00617 mmHg at 25°C and a logP value of approximately 1.15, indicating balanced lipophilicity for formulation purposes. It exhibits solubility in alcohol and limited solubility in water, with experimental solubility around 17,200 mg/L at 13°C. The flash point is reported at 284°F (approximately 140°C), signifying a relatively low flammability risk under typical conditions. These physical and chemical characteristics influence its handling, formulation, and stability in flavor and fragrance applications.
FAQ
What is 2,6-dimethoxyphenol and what are its main characteristics?
2,6-dimethoxyphenol is an organic compound classified as a phenolic derivative with two methoxy groups and one hydroxyl group on a benzene ring. It has a molecular formula C8H10O3 and is characterized by a smoky and medicinal aroma. The compound appears as a crystalline solid and is also known by synonyms such as syringol and 1,3-dimethoxy-2-hydroxybenzene. Its sensory profile includes strong smoky odors, with additional balsamic and phenolic notes described in dilute solutions.
Where does 2,6-dimethoxyphenol naturally occur and how is it used?
This compound is naturally present in substances like beechwood tar creosote, dried bonito, coffee, maple syrup, hardwood smoke, tea, fire-cured tobacco, whiskey, and wine. Its occurrence is linked to the partial combustion and thermal degradation of lignin in wood and plant materials. Industrially, it is employed as a flavor and fragrance agent to provide smoky, medicinal, and creamy notes. It is commonly used in flavoring smoked meats, bacon, nuts, and smoked fish products, enhancing their characteristic aromas.
What are the regulatory considerations and safety guidelines for 2,6-dimethoxyphenol?
2,6-dimethoxyphenol is recognized by regulatory bodies such as FEMA (US), where it is assigned FEMA number 3137 and is generally regarded as safe in flavoring applications within defined usage levels. The compound is classified as harmful if swallowed and irritating to eyes, skin, and respiratory system as per European classifications. Usage recommendations limit its concentration in fragrance concentrates to a maximum of 0.1%. Safety data include oral toxicity studies in rats and mice, and it requires appropriate handling to minimize exposure. Regulatory assessments from EFSA and JECFA provide additional evaluations of its safety profile in food and flavor uses.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2,6-dimethoxyphenol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 91-10-1 |
| Pubchem (cid): | 7041 |
| Pubchem (sid): | 134971435 |
| Flavornet: | 91-10-1 |
| Pherobase: | View |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| Metabolomics Database: | Search |
| KEGG (GenomeNet): | C10787 |
| HMDB (The Human Metabolome Database): | HMDB34158 |
| FooDB: | FDB012443 |
| Export Tariff Code: | 2909.50.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | 2,6-dimethoxyphenol |
| Trivial Name | 2,6-Dimethoxyphenol |
| Short Description | 1,3-dimethoxy-2-hydroxybenzene |
| Formula | C8 H10 O3 |
| CAS Number | 91-10-1 |
| FEMA Number | 3137 |
| Flavis Number | 4.036 |
| ECHA Number | 202-041-1 |
| FDA UNII | 4UQT464H8K |
| Nikkaji Number | J27.321J |
| Beilstein Number | 1526871 |
| MDL | MFCD00064434 |
| COE Number | 2233 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 721 2,6-dimethoxyphenol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 91-10-1 ; 2,6-DIMETHOXYPHENOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 154.16529846191 |
| Melting Point | 54 to 57°C @ 760 mm Hg |
| Boiling Point | 260 to 261°C @ 760 mm Hg |
| Vapor Pressure | 0.00617 mmHg @ 25 °C |
| Flash Point TCC Value | 140 °C TCC |
| logP (o/w) | 1.15 |
| Solubility | |
| alcohol | Yes |
| water, 17200 mg/L @ 13C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Smoky | |
| smoky, phenolic, balsamic, bacon, powdery, woody, sweet, medicinal | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | 356 hour(s) at 100.00 % |
| Luebke, William tgsc, (1995) | At 1.00 % in dipropylene glycol. smoky phenolic balsamic bacon powdery woody |
| Mosciano, Gerard P&F 19, No. 1, 27, (1994) | Sweet, phenol, smoky, medicinal, balsamic |
| Flavor Type: Medicinal | |
| sweet, medicinal, creamy, meaty, vanilla, spicy | |
| Mosciano, Gerard P&F 19, No. 1, 27, (1994) | At 60.00 ppm. Sweet, medicinal, creamy, meaty, vanilla, spice |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Coffee , Licorice , Saffron , Vanilla |
| Flavoring purposes | Bacon , Meat smoked meat , Nut , Salmon smoked salmon , Smoke |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 550 mg/kg BEHAVIORAL: GENERAL ANESTHETIC Folia Medica Cracoviensia. Vol. 32, Pg. 309, 1991. oral-mouse LD50 2500 mg/kg Bromatologia i Chemia Toksykologiczna. Vol. 14, Pg. 301, 1981. oral-rat LD50 [sex: M,F] 790 mg/kg (Piccirillo & Hartman, 1982) intravenous-cat LDLo 100 mg/kg SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA British Journal of Pharmacology. Vol. 53, Pg. 93, 1975. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for 2,6-dimethoxyphenol usage levels up to: | |||
| 0.1000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 5.40 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 12.00 (μg/capita/day) | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 4. Update in publication number(s): 29 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 1.50000 | 5.00000 | |
| beverages(nonalcoholic): | 2.00000 | 5.00000 | |
| beverages(alcoholic): | 0.05000 | 10.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | 2.00000 | 2.00000 | |
| frozen dairy: | 2.00000 | 5.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 2.00000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 4.00000 | 18.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 2.00000 | 5.00000 | |
| soups: | 0.10000 | 0.80000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25 View page or View pdf |
| Scientific Opinion on the safety and efficacy of phenol derivatives containing ring-alkyl, ring-alkoxy and side-chains with an oxygenated functional group (chemical group 25) when used as flavourings for all species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA GENetic TOXicology:Search |
| EPA Substance Registry Services (TSCA):91-10-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7041 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2,6-dimethoxyphenol |
| Chemidplus:0000091101 |
| RTECS:SL0900000 for cas# 91-10-1 |