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2,6,6-trimethyl-2-hydroxycyclohexanone
2,6,6-trimethyl-2-hydroxycyclohexanone is a flavor and fragrance compound known for its sweet tobacco aroma and presence in various teas and endive.
General Material Description
2,6,6-trimethyl-2-hydroxycyclohexanone is a cyclohexanone derivative characterized by the molecular formula C9H16O2. It appears as a compound contributing odor properties described as sweet tobacco with herbal nuances. Known by several synonyms including 2-hydroxy-2,6,6-trimethylcyclohexanone and NSC 401666, this compound links to flavor and fragrance applications. It is documented in controlled-vocabulary databases such as PubChem. Derived typically via synthetic means, it is used to impart characteristic tobacco-like notes in flavor formulations and fragrances. The compound plays a role in replicating natural aroma profiles in food and cosmetic products.
Occurrence, Applicability & Potential Uses
This compound occurs naturally in plants such as endive and various types of teas, including black, green, and oolong varieties, contributing to their distinctive aromatic profiles. Its primary application is in flavor and fragrance industries where it functions as a tobacco-scented agent. Regulatory assessment by FEMA (US) assigns it the number 4531, indicating its recognition for safe use levels in flavor formulations. It is utilized to enhance or replicate sweet tobacco and herbal odor notes in food products and perfumes. The compound’s stability and odor potency make it valuable for creating complex sensory experiences in beverages and aromatic blends.
Physico-Chemical Properties Summary
2,6,6-trimethyl-2-hydroxycyclohexanone exhibits moderate volatility with a boiling point ranging approximately from 232 to 233°C at standard atmospheric pressure. Its specific gravity near 0.99 at 20°C and refractive index between 1.466 and 1.472 suggest a liquid phase under ambient conditions with typical density for flavor compounds. The vapor pressure is low at 0.011 mmHg at 25°C, indicating limited evaporation at room temperature. Solubility in alcohol is confirmed, whereas its solubility in water is limited, estimated at around 6304 mg/L at 25°C. The estimated logP value near 0.9 implies moderate lipophilicity, which influences its behavior in formulations and its olfactory delivery. Such physicochemical traits support its use in diverse flavor and fragrance matrices, balancing volatility and solubility.
FAQ
What is 2,6,6-trimethyl-2-hydroxycyclohexanone and what are its sensory characteristics?
2,6,6-trimethyl-2-hydroxycyclohexanone is a chemical compound belonging to the cyclohexanone class, used primarily in flavor and fragrance applications. It is noted for a sweet tobacco-like odor with herbal undertones, making it popular for imparting tobacco scents in various products. The compound is also identified under synonyms such as 2-hydroxy-2,6,6-trimethylcyclohexanone and NSC 401666.
Where is 2,6,6-trimethyl-2-hydroxycyclohexanone naturally found and how is it applied in industry?
This compound naturally occurs in certain plants including endive and several types of tea such as black, green, and oolong teas, contributing to their complex aroma profiles. Industrially, it is utilized by flavor and fragrance manufacturers to replicate tobacco and herbal notes in products such as beverages, confections, and perfumery. Its chemical properties support use in diverse formulation types due to moderate solubility in alcohol and stability in mixtures.
What are the regulatory standards and safety considerations associated with 2,6,6-trimethyl-2-hydroxycyclohexanone?
Regulatory bodies recognize 2,6,6-trimethyl-2-hydroxycyclohexanone with FEMA number 4531, where the FEMA Expert Panel has evaluated its safety for use as a flavoring substance in food and beverages. The compound has no classified hazards under OSHA (US) GHS standards, and precautionary statements are not required. It is listed in safety assessments by IFRA with usage guidelines to ensure consumer safety. No oral, dermal, or inhalation toxicities have been definitively determined, but safe use levels exist within food and fragrance applications.
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 |
| HMDB (The Human Metabolome Database): | HMDB37023 |
| FooDB: | FDB016003 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | 2,6,6-Trimethyl-2-hydroxycyclohexanone |
General Material Information
| Preferred name | 2,6,6-trimethyl-2-hydroxycyclohexanone |
| Trivial Name | 2-Hydroxy-2,6,6-trimethylcyclohexanone |
| Short Description | cyclohexanone, 2-hydroxy-2,6,6-trimethyl- |
| Formula | C9 H16 O2 |
| CAS Number | 7500-42-7 |
| FEMA Number | 4531 |
| FDA UNII | MH0UUM21K0 |
| Nikkaji Number | J439.304J |
| xLogP3-AA | 1.30 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 2054 2,6,6-trimethyl-2-hydroxycyclohexanone |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 7500-42-7 ; 2,6,6-TRIMETHYL-2-HYDROXYCYCLOHEXANONE |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 156.22491455078 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.231 to 8.281 |
| Refractive Index | 1.466 to 1.472 @ 20 °C |
| Boiling Point | 232 to 233°C @ 760 mm Hg |
| Boiling Point | 58 to 65°C @ 4 mm Hg |
| Vapor Pressure | 0.011 mmHg @ 25 °C |
| Flash Point TCC Value | 94.44 °C TCC |
| logP (o/w) | 0.924 est |
| Solubility | |
| alcohol | Yes |
| water, 6304 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Tobacco | |
| sweet, tobacco, herbal | |
| General comment | At 100.00 %. sweet tobacco herbal |
Occurrences
| (data available) |
Safety Information
Safety information
| 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: | |
| Not determined | |
| 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 | |||
| Structure Class: | II | ||
| 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: 24 | |||
| Click here to view publication 24 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | 0.01000 | 0.10000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 0.01000 | 0.10000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | 1.00000 | 5.00000 | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | 1.00000 | 10.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| 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 :101115 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2-hydroxy-2,6,6-trimethylcyclohexan-1-one |
| Chemidplus:0007500427 |