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cinnamyl nitrile
Cinnamyl nitrile is a chemical compound with a spicy cinnamon aroma used primarily as a fragrance agent in perfumery.
General Material Description
Cinnamyl nitrile, also known by synonyms including cinnamonitrile and 3-phenyl acrylonitrile, is an organic nitrile compound with the molecular formula C9H7N. It appears as a colorless to pale liquid with a characteristic spicy cinnamon-like odor, making it valuable in fragrance formulations. Structurally, it consists of a phenyl ring attached to an unsaturated nitrile group (–C≡N), as defined by its standardized chemical identifiers and InChI. This compound is typically derived synthetically but can be found naturally at trace levels in materials such as champaca concrete and fig leaf extracts. For detailed chemical information, see its PubChem entry. Its olfactory properties contribute to its use in perfuming agents within the fragrance industry.
Occurrence, Applicability & Potential Uses
Cinnamyl nitrile naturally occurs at trace concentrations in botanical materials such as champaca concrete and fig leaf extracts. Its pronounced spicy, cinnamon-like odor makes it applicable as a fragrance agent, imparting cassia and spice notes within perfume blends. It is recognized in the fragrance sector under standards such as IFRA (Global), where usage restrictions are applied to ensure safety, particularly regarding dermal sensitization effects. The compound is primarily employed for its scent profile in perfuming agents and is not used as a flavoring ingredient due to regulatory and safety considerations.
Physico-Chemical Properties Summary
Cinnamyl nitrile exhibits physical properties that influence its handling and formulation in fragrance products. It has a molecular weight of approximately 129.16 g/mol and displays moderate volatility with a boiling point range of 263 to 264 °C at atmospheric pressure (760 mm Hg). Its vapor pressure is low, about 0.01 mmHg at 25 °C, indicating limited evaporation at room temperature. The compound has moderate lipophilicity with an estimated logP value near 2.0, which affects its solubility profile—it is soluble in alcohol and shows limited solubility in water around 1067 mg/L at 25 °C. The flash point is about 105 °C (221 °F), which guides safe storage and use considerations. These physico-chemical characteristics support its use in liquid fragrance formulations and influence its volatility and persistence on skin or substrates.
FAQ
What is cinnamyl nitrile and what are its key characteristics?
Cinnamyl nitrile is an organic compound with the molecular formula C9H7N, characterized by a phenyl group attached to a nitrile moiety. It is known for its spicy, cinnamon-like odor and is primarily utilized as a fragrance ingredient. The compound is a colorless to pale liquid with moderate volatility and solubility properties suitable for perfumery applications. It exists naturally at trace levels in certain botanical extracts such as champaca concrete and fig leaf.
Where is cinnamyl nitrile found and how is it used in industry?
Cinnamyl nitrile occurs in nature at trace concentrations within plant materials including champaca concrete and fig leaf. Industrially, it is synthesized and employed mainly as a fragrance agent to impart spicy and cinnamon notes in perfumes and other scented products. The compound’s physical and chemical properties support its incorporation into liquid fragrance formulations, where its moderate volatility and solubility facilitate desirable scent release profiles. It is not used as a flavoring substance due to safety and regulatory factors.
What regulations govern the use and safety of cinnamyl nitrile?
The usage of cinnamyl nitrile in fragrances is regulated under standards such as the IFRA Code of Practice (Global), which addresses exposure limits and safety concerns including potential dermal sensitization. IFRA specifies maximum concentration limits for various product categories to ensure consumer safety. Additionally, cinnamyl nitrile’s safety data include established oral and dermal toxicity thresholds in animal studies, although no specific GHS hazard classifications apply. Regulatory bodies require adherence to these guidelines to control its concentration in consumer products and prevent adverse reactions.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| 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 |
| FooDB: | FDB012054 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | cinnamyl nitrile |
| Trivial Name | Cinnamonitrile |
| Short Description | cinnamonitrile |
| Formula | C9 H7 N |
| CAS Number | 4360-47-8 |
| Deleted CAS Number | 132721-34-7 |
| ECHA Number | 224-441-5 |
| FDA UNII | Search |
| Beilstein Number | 1209545 |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 129.16178894043 |
| Boiling Point | 263 to 264°C @ 760 mm Hg |
| Vapor Pressure | 0.01 mmHg @ 25 °C |
| Flash Point TCC Value | 105 °C TCC |
| logP (o/w) | 2.008 est |
| Solubility | |
| alcohol | Yes |
| water, 1067 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| spicy, cinnamon, cassia | |
| General comment | At 10.00 % in dipropylene glycol. spicy cinnamon nitrile |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Cassia , Cinnamon , Spice |
| Cosmetic purposes | Perfuming agents |
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: | |
| oral-rat LD50 4150 mg/kg Food and Cosmetics Toxicology. Vol. 14, Pg. 721, 1976. intravenous-rabbit LDLo 34 mg/kg Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 153, Pg. 895, 1911. | |
| Dermal Toxicity: | |
| subcutaneous-guinea pig LDLo 130 mg/kg Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 153, Pg. 895, 1911. | |
| 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 | |||
| IFRA Critical Effect: | |||
| Dermal sensitization | |||
| View the IFRA Standard | |||
| View IFRA Standards Library for complete information. | |||
| Please review Amendment 49 IFRA documentation for complete information. | |||
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%): | |||
| Category 1: Products applied to the lips | |||
| 0.077 % | |||
| Category 2: Products applied to the axillae | |||
| 0.023 % | |||
| Category 3: Products applied to the face/body using fingertips | |||
| 0.46 % | |||
| Category 4: Products related to fine fragrance | |||
| 0.43 % | |||
| Category 5: Products applied to the face and body using the hands (palms), primarily leave-on | |||
| Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on | |||
| 0.11 % | |||
| Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on | |||
| 0.11 % | |||
| Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on | |||
| 0.11 % | |||
| Category 5D: Baby Creams, baby Oils and baby talc | |||
| 0.11 % | |||
| Category 6: Products with oral and lip exposure | |||
| 0.25 % | |||
| Category 7: Products applied to the hair with some hand contact | |||
| Category 7A: Rinse-off products applied to the hair with some hand contact | |||
| 0.88 % | |||
| Category 7B: Leave-on products applied to the hair with some hand contact | |||
| 0.88 % | |||
| Category 8: Products with significant anogenital exposure | |||
| 0.045 % | |||
| Category 9: Products with body and hand exposure, primarily rinse off | |||
| 0.84 % | |||
| Category 10: Household care products with mostly hand contact | |||
| Category 10A: Household care excluding aerosol products (excluding aerosol/spray products) | |||
| 3.00 % | |||
| Category 10B: Household aerosol/spray products | |||
| 3.00 % | |||
| Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate | |||
| Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure | |||
| 1.70 % | |||
| Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure | |||
| 1.70 % | |||
| Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin | |||
| No Restriction | |||
| Notes: | |||
| IFRA FLAVOR REQUIREMENTS: | |||
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards. | |||
| Recommendation for cinnamyl nitrile 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):4360-47-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :74667 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3-phenylprop-2-enenitrile |
| Chemidplus:0004360478 |