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2,4,6-trimethyl phenol
2,4,6-trimethyl phenol is a phenolic compound with a characteristic mild phenolic coffee grounds odor and flavor, used as a flavor and fragrance agent.
General Material Description
2,4,6-trimethyl phenol is an aromatic organic compound classified as a phenol derivative with the molecular formula C9H12O. It appears as a colorless to pale liquid or solid depending on conditions, featuring a distinct mild phenolic odor reminiscent of coffee grounds. Known also by synonyms such as mesitol and 2-hydroxymesitylene, this compound is a chemical intermediate and flavor agent. It is sourced synthetically and can be found naturally in small amounts in plants like Prunus mahaleb. The compound’s sensory profile includes phenolic notes important in flavor and fragrance applications. For detailed chemical taxonomy and properties, readers may refer to its entry in PubChem.
Occurrence, Applicability & Potential Uses
2,4,6-trimethyl phenol occurs naturally in trace amounts in the seeds of Prunus mahaleb, a species used traditionally for flavoring. Its pleasant phenolic odor and flavor attributes make it applicable as a component in flavor and fragrance formulations. The compound serves as a functional ingredient that contributes mild phenolic coffee-like notes. It is recognized and regulated under FEMA (US) with FEMA number 4329, indicating its acknowledged status as a flavoring substance. The range of uses extends across various food categories including baked goods, beverages, dairy, and confectionery, where it imparts subtle sensory effects consistent with its phenol derivative class properties.
Physico-Chemical Properties Summary
2,4,6-trimethyl phenol displays physical characteristics relevant to formulation and handling. It melts between 73 and 74°C at standard atmospheric pressure. The compound's vapor pressure at 25°C is low (approximately 0.1 mmHg), indicating limited volatility under ambient conditions. Its estimated logP value of 2.7 suggests moderate hydrophobicity, affecting solubility and distribution in formulations. Solubility varies; it is moderately soluble in alcohol and experimental data specify approximately 1200 mg/L solubility in water at 25°C, while it is considered not soluble in pure water under certain conditions. The flash point near 96°C (206°F) requires appropriate storage precautions. To maintain stability, 2,4,6-trimethyl phenol should be stored in tightly sealed containers away from heat and light, preferably in cool, dry environments. Typical shelf life extends to 24 months or longer when properly stored.
FAQ
What is 2,4,6-trimethyl phenol and what are its key characteristics?
2,4,6-trimethyl phenol is a phenolic aromatic compound characterized by three methyl groups attached to a phenol ring. It exhibits a mild phenolic odor and flavor often described as resembling coffee grounds. This compound is employed as a flavor and fragrance agent and appears naturally in trace amounts in certain plants. Also known as mesitol or 2-hydroxymesitylene, it acts as a chemical intermediate with specific sensory properties valuable in product formulation.
Where is 2,4,6-trimethyl phenol found and how is it typically used?
This compound occurs naturally, notably in Prunus mahaleb seeds, but is commonly produced synthetically for commercial use. In the flavor and fragrance industry, it is utilized to impart phenolic, coffee-like sensory notes in various products. Its applications include incorporation into baked goods, beverages (both alcoholic and nonalcoholic), dairy, confectionery, and seasonings. Regulatory bodies such as FEMA (US) have assigned it a flavoring substance number, recognizing its role within defined usage levels.
What safety regulations and storage considerations apply to 2,4,6-trimethyl phenol?
2,4,6-trimethyl phenol is regulated under FEMA (US) and EFSA (EU) frameworks, with documented flavor usage levels to ensure safety in consumer products. Handling precautions stem from its corrosive nature, classified as causing burns, necessitating protective measures such as gloves and eye protection during use. It should be stored in cool, dry places within tightly sealed containers, protected from heat and light, to maintain stability. The compound has a shelf life of approximately 24 months when correctly stored. Toxicology studies report relatively low acute oral toxicity, but safe handling practices remain essential.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2,4,6-trimethylphenol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 527-60-6 |
| Pubchem (cid): | 10698 |
| Pubchem (sid): | 134978605 |
| Publications by US Patents | |
| 3,946,080 - Flavouring and perfuming ingredients | |
| Furfurylthioacetone | |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB32544 |
| FooDB: | FDB010421 |
| Export Tariff Code: | 2907.19.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| FAO: | 2,4,6-Trimethylphenol |
General Material Information
| Preferred name | 2,4,6-trimethyl phenol |
| Trivial Name | 2,4,6-Trimethylphenol |
| Short Description | 2,4,6-trimethylphenol |
| Formula | C9 H12 O |
| CAS Number | 527-60-6 |
| FEMA Number | 4329 |
| Flavis Number | 4.095 |
| ECHA Number | 208-419-2 |
| FDA UNII | FPZ32614N6 |
| Nikkaji Number | J6.671K |
| Beilstein Number | 1859675 |
| MDL | MFCD00002235 |
| xLogP3-AA | 2.70 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 2013 2,4,6-trimethylphenol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 527-60-6 ; 2,4,6-TRIMETHYLPHENOL |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
| Penta International | Santa Cruz Biotechnology |
| Sigma-Aldrich | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 136.19383239746 |
| Melting Point | 73 to 74°C @ 760 mm Hg |
| Vapor Pressure | 0.1 mmHg @ 25 °C |
| Flash Point TCC Value | 96.67 °C TCC |
| logP (o/w) | 2.73 |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| water, 1200 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Phenolic | |
| phenolic, coffee | |
| General comment | At 0.10 % in propylene glycol. mild phenolic coffee grounds |
| Flavor Type: Phenolic | |
| phenolic, coffee | |
| General comment | Phenolic coffee grounds |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| C - Corrosive. | |
| R 34 - Causes burns. 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. S 45 - In case of accident or if you feel unwell seek medical advice immediately. | |
| 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-mouse LD50 10000 mg/kg Bromatologia i Chemia Toksykologiczna. Vol. 14, Pg. 301, 1981. intraperitoneal-mouse LD50 > 1000 mg/kg Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 201, 1960. | |
| 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 | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.0097 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 420 (μg/person/day) | ||
| Threshold of Concern: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| 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: 23 | |||
| Click here to view publication 23 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.10000 | 0.50000 | |
| beverages(nonalcoholic): | 1.00000 | 5.00000 | |
| beverages(alcoholic): | 1.00000 | 5.00000 | |
| breakfast cereal: | - | - | |
| cheese: | 0.01000 | 0.05000 | |
| chewing gum: | - | - | |
| condiments / relishes: | 0.01000 | 0.05000 | |
| confectionery froastings: | 1.00000 | 5.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | 0.01000 | 0.05000 | |
| frozen dairy: | 0.01000 | 0.05000 | |
| fruit ices: | 0.10000 | 0.50000 | |
| gelatins / puddings: | 0.01000 | 0.05000 | |
| granulated sugar: | - | - | |
| gravies: | 0.01000 | 0.05000 | |
| hard candy: | - | - | |
| imitation dairy: | 0.01000 | 0.05000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.01000 | 0.05000 | |
| milk products: | 0.01000 | 0.05000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | 0.01000 | 0.05000 | |
| processed fruits: | 0.01000 | 0.05000 | |
| processed vegetables: | 0.01000 | 0.05000 | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 0.01000 | 0.05000 | |
| snack foods: | 0.01000 | 0.05000 | |
| soft candy: | - | - | |
| soups: | 0.01000 | 0.05000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 0.01000 | 0.05000 | |
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 0.50000 | 2.50000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.20000 | 1.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.50000 | 2.50000 | |
| Processed fruit (04.1): | 0.40000 | 2.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 1.00000 | 5.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.20000 | 1.00000 | |
| Bakery wares (07.0): | 2.00000 | 10.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.20000 | 1.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.20000 | 1.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.30000 | 1.50000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.50000 | 2.50000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.20000 | 1.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 | |
| Ready-to-eat savouries (15.0): | 2.00000 | 10.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.40000 | 2.00000 | |
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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):527-60-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :10698 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2430 |
| WGK Germany:2 |
| 2,4,6-trimethylphenol |
| Chemidplus:0000527606 |
| RTECS:OX6590000 for cas# 527-60-6 |