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4-allyl-2,6-dimethoxyphenol
4-allyl-2,6-dimethoxyphenol is a phenolic compound with a smoky, meaty scent used as a flavoring agent in food products like bacon and spices.
General Material Description
4-allyl-2,6-dimethoxyphenol, also known by synonyms including 6-methoxyeugenol and 4-allyl syringol, is a phenolic compound with the molecular formula C11H14O3. It appears as a colorless to pale liquid featuring characteristic meaty and smoky sensory notes. This compound is structurally related to eugenol and syringol derivatives and is found naturally in various plants and foodstuffs. It is listed under the controlled vocabulary entry for phenolic substances in PubChem, facilitating chemical data reference and research. Sourced primarily from natural extracts such as nutmeg and parsley leaf oil, it serves a significant role as a flavoring agent, imparting savory and smoky nuances in food systems.
Occurrence, Applicability & Potential Uses
4-allyl-2,6-dimethoxyphenol occurs naturally in diverse botanical sources such as banana fruit, buchu plant, nutmeg seed, parsley leaf oil, and wine. Its presence in these natural products contributes to characteristic aroma profiles associated with these items. In flavor applications, it is used for its meaty, smoky, and spicy notes, often enhancing bacon, burnt, tobacco, hawthorn, spice, and vanilla aromas. Regulatory evaluation by FEMA (US) and JECFA (international) recognizes this compound's application as a flavoring agent, confirming its utility in seasoning and flavor enhancement while adhering to safety standards as established in these regions.
Physico-Chemical Properties Summary
This compound has a molecular weight of approximately 194.23 g/mol and presents as a liquid with specific gravity between 1.089 and 1.095 at 25 °C. Its refractive index ranges from 1.548 to 1.55 at 20 °C, indicating moderate optical density. Boiling points are reported near 168 to 169 °C at reduced pressure (11 mm Hg) and about 300 to 301 °C at atmospheric pressure (760 mm Hg). The flash point is approximately 110 °C (230 °F), reflecting moderate volatility. Its log P value, estimated at around 2.34, suggests lipid solubility conducive to incorporation in flavor formulations. The compound exhibits low vapor pressure at 25 °C and moderate solubility in alcohol and limited solubility in water, guiding its use in various food product matrices.
FAQ
What is 4-allyl-2,6-dimethoxyphenol and what are its primary characteristics?
4-allyl-2,6-dimethoxyphenol, also known as 6-methoxyeugenol or 4-allyl syringol, is a phenolic compound with a molecular formula C11H14O3. It is a colorless to pale liquid featuring a meaty, smoky aroma profile with sweet and woody undertones. The compound is used primarily as a flavoring agent due to its distinctive sensory properties that combine phenolic, smoky, and vanilla notes. It naturally occurs in plants and natural food products such as nutmeg, banana, and parsley leaf oil.
Where is 4-allyl-2,6-dimethoxyphenol found naturally and how is it used in products?
This compound occurs in several botanical sources including banana fruit, buchu, nutmeg seed, parsley leaf oil, and wine. Its natural presence contributes to the characteristic flavors and aromas of these foods and beverages. It is popularly applied as a flavor additive to replicate or enhance savory and smoked notes in meat products, spices, tobacco aromas, and various flavor blends. Its usage supports the development of flavors described as smoky, bacon-like, and spicy with vanilla nuances.
What regulations govern the use and safety of 4-allyl-2,6-dimethoxyphenol in food products?
Regulatory bodies such as FEMA (US) and JECFA (international) have evaluated 4-allyl-2,6-dimethoxyphenol for use as a flavoring agent, assigning FEMA number 3655 and JECFA number 726 respectively. The compound is recognized within acceptable use levels in foods and beverages under these frameworks. Safety assessments include toxicity data and purity specifications, although it is not approved for fragrance applications according to IFRA (Global) guidelines. Compliance with regional regulations ensures its safe incorporation into food flavorings.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
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 |
| HMDB (The Human Metabolome Database): | HMDB41194 |
| FooDB: | FDB021092 |
| YMDB (Yeast Metabolome Database): | YMDB01614 |
| Export Tariff Code: | 2909.50.0090 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 4-allyl-2,6-dimethoxyphenol |
| Trivial Name | 4-Allyl-2,6-dimethoxyphenol |
| Short Description | 6-methoxyeugenol |
| Formula | C11 H14 O3 |
| CAS Number | 6627-88-9 |
| FEMA Number | 3655 |
| Flavis Number | 4.051 |
| ECHA Number | 229-600-2 |
| FDA UNII | 8VF00YWP89 |
| Nikkaji Number | J13.307H |
| MDL | MFCD00008655 |
| COE Number | 11214 |
| xLogP3-AA | 2.60 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 726 4-allyl-2,6-dimethoxyphenol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 6627-88-9 ; 4-ALLYL-2,6-DIMETHOXYPHENOL |
| Synonyms |
|
Suppliers
| BOC Sciences | Carbosynth |
| Endeavour Specialty Chemicals | Penta International |
| R C Treatt & Co Ltd | Robinson Brothers |
| Sigma-Aldrich | Synerzine |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 194.23017883301 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.062 to 9.111 |
| Refractive Index | 1.548 to 1.55 @ 20 °C |
| Boiling Point | 168 to 169°C @ 11 mm Hg |
| Boiling Point | 300 to 301°C @ 760 mm Hg |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.338 est |
| Solubility | |
| alcohol | Yes |
| water, 307.4 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Meaty | |
| roasted, burnt, meaty roasted meaty, bacon, smoky, ham, meaty, phenolic, sweet, woody | |
| General comment | At 1.00 % in propylene glycol. roasted burnt meaty bacon smoky ham |
| Mosciano, Gerard P&F 19, No. 3, 51, (1994) | Smoky, meaty, phenolic, sweet, ham and woody |
| Flavor Type: Meaty | |
| meaty, phenolic, smoky, bacon, creamy, vanilla | |
| Mosciano, Gerard P&F 19, No. 3, 51, (1994) | At 20.00 ppm. Meaty, phenolic, smoky and bacony, with creamy vanilla nuances |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Hawthorn , Tobacco |
| Flavoring purposes | Bacon , Burnt , Smoke , Spice , Vanilla |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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 [sex: M,F] 2000 mg/kg (Piccirillo & Hartman, 1982) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| IFRA Purity Specification: | |||
| Recommendation for 4-allyl-2,6-dimethoxyphenol usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 6.00 (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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | 0.50000 | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 5.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.50000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.50000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | 0.20000 | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | 5.00000 | |
| snack foods: | - | 0.50000 | |
| soft candy: | - | - | |
| soups: | - | 0.20000 | |
| 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 |
| 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 allylhydroxybenzenes (chemical group 18) when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :226486 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2,6-dimethoxy-4-prop-2-enylphenol |
| Chemidplus:0006627889 |