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citronellal oxime
Citronellal oxime is a citrus-scented fragrance compound used primarily for its lime and bergamot-like odor in perfumery and aroma formulations.
General Material Description
Citronellal oxime is a synthetic organic compound classified under oximes derived from aldehydes, specifically 3,7-dimethyl-6-octenal. Its molecular formula is C10H19NO, and it commonly appears as a pale liquid. The compound exhibits a distinct citrus odor reminiscent of bergamot and lime. Known also by synonyms such as 3,7-dimethyl-6-octenaldoxime and N-(3,7-dimethyloct-6-enylidene)hydroxylamine, citronellal oxime is listed on chemical databases including PubChem. It is primarily synthesized for use in fragrance applications, obtained typically through the oximation of citronellal. This compound contributes fresh, citrusy notes to flavor and fragrance formulations.
Occurrence, Applicability & Potential Uses
Citronellal oxime does not naturally occur in significant quantities in biological systems but is manufactured for its fragrance characteristics. It is widely applied as an odorant with prominent citrus and lime nuances, used especially in perfumery and aroma compositions. The compound is recognised under the FEMA (US) standard for fragrance agents, reflecting its acceptance in the industry for olfactory purposes. It enhances freshness in scent profiles and is valued for imparting citrus notes reminiscent of bergamot. Potential uses extend to applications requiring citrus aroma contributions where its moderate volatility allows balanced scent release.
Physico-Chemical Properties Summary
Citronellal oxime has a molecular weight of approximately 169.27 g/mol and an estimated partition coefficient (log P) of around 3.25, indicating moderate lipophilicity. Its vapor pressure at 25 °C is very low (0.002 mmHg), consistent with limited volatility suitable for sustained fragrance release. The compound is soluble in alcohol solvents and exhibits slight water solubility estimated at 64.78 mg/L at room temperature, which affects its miscibility in aqueous versus non-aqueous formulations. The flash point of 317 °F (about 158 °C) highlights its relatively low flammability risk during handling. These physical and chemical properties influence its selection and stability within fragrance products.
FAQ
What is citronellal oxime and how is it used in fragrances?
Citronellal oxime is an oxime derivative of citronellal with the molecular formula C10H19NO. It is primarily used as a fragrance agent due to its citrus and lime odor notes. This compound adds fresh, bergamot-like nuances to perfumery compositions, enhancing their olfactory complexity. Its use is limited to aroma applications rather than flavorings.
Where does citronellal oxime occur and what are its chemical characteristics?
Citronellal oxime is not naturally abundant but synthesized through chemical modification of citronellal. It is a pale liquid exhibiting moderate lipophilicity with an estimated log P near 3.25. The compound has low vapor pressure at room temperature, making it less volatile compared to some aroma chemicals, and dissolves well in alcohol. Its relatively high flash point supports safe handling in industrial settings.
What regulations or safety standards apply to citronellal oxime in the fragrance industry?
Citronellal oxime is recognized within the FEMA (US) framework as a fragrance agent. According to IFRA (Global), usage guidelines exist to ensure safe concentration limits in perfumes and related products. No specific hazard classifications under OSHA regulations have been assigned. While no data supports its use as a flavoring, its fragrance use is subject to standardized industry controls to maintain consumer safety.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
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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 |
| ChemSpider: | View |
General Material Information
| Preferred name | citronellal oxime |
| Trivial Name | 6-Octenal, 3,7-dimethyl-, oxime |
| Short Description | 3,7-dimethyl-6-octenaldoxime |
| Formula | C10 H19 N O |
| CAS Number | 22457-25-6 |
| ECHA Number | 245-011-3 |
| FDA UNII | Search |
| xLogP3-AA | 3.20 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 169.26762390137 |
| Vapor Pressure | 0.002 mmHg @ 25 °C |
| Flash Point TCC Value | 158.1 °C TCC |
| logP (o/w) | 3.253 est |
| Solubility | |
| alcohol | Yes |
| water, 64.78 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Citrus | |
| citrus, bergamot, lime | |
| General comment | At 100.00 %. citrus bergamot lime |
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: | |||
| 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 citronellal oxime 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):22457-25-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :89723 |
| National Institute of Allergy and Infectious Diseases:Data |
| N-(3,7-dimethyloct-6-enylidene)hydroxylamine |
| Chemidplus:0022457256 |