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trimethyl-3-cyclopentenyl acetonitrile
Trimethyl-3-cyclopentenyl acetonitrile is a chemical fragrance agent noted for its medium pine odor and use in perfuming applications.
General Material Description
Trimethyl-3-cyclopentenyl acetonitrile is a synthetic chemical compound classified primarily as a fragrance material. It appears as a colorless to pale liquid and is characterized by a distinctive medium-strength pine odor, often described alongside herbal and hay-like notes. This compound is known by several synonyms, including 'cantryl' as a trade name used by Symrise, and its systematic IUPAC equivalent is 2,2,3-trimethyl-3-cyclopentene-1-acetonitrile. The molecular formula is C10H15N, and it has a molecular weight near 149.24 g/mol. Trimethyl-3-cyclopentenyl acetonitrile can be sourced through chemical synthesis involving cyclopentene intermediates and cyanide or nitrile functionalization, and it is included in chemical databases such as PubChem. It is employed primarily in fragrance formulations owing to its pine-related olfactory profile.
Occurrence, Applicability & Potential Uses
This compound does not occur naturally but is synthesized for industrial use, particularly in the fragrance sector. It is applied as a perfuming agent to impart pine, rosemary, and hay-like aromas in personal care products, cleaning agents, and home fragrances. Its sensory profile makes it valuable in formulations requiring fresh, green, or woody notes. The material’s use and safety are subject to regulatory frameworks including REACH (European Union), which ensures assessment and registration for chemical substances placed on the market. Trimethyl-3-cyclopentenyl acetonitrile's stability in various matrices such as body lotion, shampoo, and household cleaners supports its versatility as a fragrance ingredient.
Physico-Chemical Properties Summary
Trimethyl-3-cyclopentenyl acetonitrile exhibits physical and chemical properties that support its application in fragrances. The compound has a boiling point range near 230–231°C at atmospheric pressure (760 mm Hg), indicating moderate volatility suitable for sustained scent release. Its specific gravity is approximately 0.91 at 25°C, reflecting a density slightly less than water, and its refractive index ranges from 1.464 to 1.469 at 20°C. The vapor pressure is low, about 0.067 mm Hg at 25°C, suggesting limited evaporation at ambient temperature. A moderate estimated logP value around 2.8 indicates moderate lipophilicity, which influences solubility and interaction with formulation components. It is soluble in alcohol and sparingly soluble in water. The flash point is about 210°F (approximately 99°C), which is relevant for handling and storage considerations. Stability tests show excellent performance in shampoos and detergents but reduced stability in bleach formulations.
FAQ
What is trimethyl-3-cyclopentenyl acetonitrile and what are its main uses?
Trimethyl-3-cyclopentenyl acetonitrile is a synthetic fragrance compound known for its distinctive pine odor. It is primarily used as a perfuming agent in various consumer products including personal care items and household cleaners. Its olfactory profile, which includes pine, rosemary, and hay-like tonalities, makes it valuable for adding fresh and green aromatic notes. It is marketed under trade names like Cantryl by fragrance manufacturers.
How is trimethyl-3-cyclopentenyl acetonitrile typically formulated and where is it used?
The compound is incorporated into fragrance compositions and personal care products such as shampoos, soaps, and lotions due to its scent and chemical stability. It exhibits good to excellent stability in formulations including body lotions and cleaners, although it is incompatible with bleach. Its moderate volatility and solubility in alcohol facilitate its use in liquid and semi-solid products. Usage concentrations generally remain controlled to maintain the desired olfactory effect without overexposure.
What regulations and safety considerations apply to trimethyl-3-cyclopentenyl acetonitrile?
Trimethyl-3-cyclopentenyl acetonitrile is regulated under REACH (European Union) which governs chemical safety and market placement. It is classified as an irritant to eyes, respiratory system, and skin under European hazard criteria but lacks specific GHS hazard labeling under OSHA HCS (United States). The compound has an oral rat LD50 greater than 2000 mg/kg indicating low acute toxicity. IFRA standards provide usage guidelines restricting its use to fragrance applications only, disallowing flavor uses. Appropriate protective measures should be taken to avoid irritation during handling.
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 |
| HMDB (The Human Metabolome Database): | Search |
| ChemSpider: | View |
General Material Information
| Preferred name | trimethyl-3-cyclopentenyl acetonitrile |
| Trivial Name | 2,2,3-Trimethyl-3-cyclopentene-1-acetonitrile |
| Short Description | cantryl (Symrise) |
| Formula | C10 H15 N |
| CAS Number | 15373-31-6 |
| Deleted CAS Number | 18674-52-7 |
| ECHA Number | 239-405-4 |
| FDA UNII | Search |
| Nikkaji Number | J218.411G |
| xLogP3-AA | 2.10 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Associate Allied Chemicals | Moellhausen |
| Penta International | Symrise |
| Tadimety Aromatics | Vigon International |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 149.23655700684 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.547 to 7.597 |
| Refractive Index | 1.464 to 1.469 @ 20 °C |
| Boiling Point | 230 to 231°C @ 760 mm Hg |
| Vapor Pressure | 0.067 mmHg @ 25 °C |
| Vapor Density | 5.2 |
| Flash Point TCC Value | 98.89 °C TCC |
| logP (o/w) | 2.837 est |
| Solubility | |
| alcohol | Yes |
| water, 59.81 mg/L @ 25 °C (est) | Yes |
| Stability | |
| AP roll-on 15% (very good) | Unspecified |
| bleach (poor) | Unspecified |
| body lotion (good) | Unspecified |
| cleaner APC liquid (very good) | Unspecified |
| cleaner liquid citric acid (excellent) | Unspecified |
| detergent powder conc. (very good) | Unspecified |
| shampoo/shower gel (excellent) | Unspecified |
| soap (very good) | Unspecified |
Organoleptic Properties
| Odor Type: Pine | |
| pine, rosemary, hay | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 44 hour(s) at 100.00 % |
| General comment | At 10.00 % in dipropylene glycol. pine rosemary hay |
| Stable in: body lotion (good), shampoo (excellent), soap (very good), ap roll-on (very good), powder (very good), cleaner citric (excellent), cleaner apc (very good), bleach (poor). | Powerful odor with pine, rosemary and hay-like tonalities |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing. | |
| 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 > 2000 mg/kg | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| 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 trimethyl-3-cyclopentenyl acetonitrile flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):15373-31-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :85833 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 2-(2,2,3-trimethyl-1-cyclopent-3-enyl)acetonitrile |
| Chemidplus:0015373316 |