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citronellal / methyl anthranilate schiff's base
Citronellal / methyl anthranilate Schiff's base is a fragrance compound exhibiting fresh citrus and woody notes, commonly used in perfuming agents.
General Material Description
Citronellal / methyl anthranilate Schiff's base is a synthetic chemical compound used extensively as a fragrance agent. It is known under multiple synonyms, including methyl 2-[(3,7-dimethyl-6-octen-1-ylidene)amino]benzoate and citronama, the latter being its trade name by IFF. This compound is classified as a Schiff base formed from the condensation of citronellal and methyl anthranilate. It appears as a clear liquid with a medium-intensity citrus odor, coupled with weedy, grassy, sharp, and woody nuances when diluted in dipropylene glycol at a 10% concentration. Its molecular formula is C18H25NO2, and it is referenced in chemical databases such as PubChem. The compound is produced via synthetic chemical processes starting from natural or synthetic citronellal and methyl anthranilate. This hybrid molecule combines characteristics of its precursor components, contributing unique olfactory properties to fragrance formulations.
Occurrence, Applicability & Potential Uses
Although citronellal / methyl anthranilate Schiff's base does not naturally occur in biological systems, it plays a role in fragrance formulation by mimicking or replacing natural scents. It is primarily employed as a fragrance ingredient to impart fresh citrus and woody aromas and is considered an alternative to palmarosa oil and lily of the valley type notes. The International Fragrance Association (IFRA) (Global) provides guidelines recommending usage levels up to 2% in fragrance concentrates due to safety considerations. Its application potential extends to perfuming agents in cosmetics and personal care products, contributing complex scent profiles that enhance product appeal.
Physico-Chemical Properties Summary
The compound has a molecular weight of approximately 287.4 g/mol and exhibits a moderate lipophilicity, with an estimated logP value of 7.08. It is a clear liquid with a refractive index ranging from 1.5125 to 1.5225 at 20°C and a specific gravity between 1.0055 and 1.0135 at 25°C, reflecting moderate density. The boiling point lies between 408 and 409°C at standard atmospheric pressure (760 mm Hg). Its flash point is around 200°F, indicating relatively low flammability under typical handling conditions. The substance is soluble in alcohol and sparingly soluble in water, with a solubility estimate of 0.2826 mg/L at 25°C. These characteristics influence its formulation behavior, affecting volatility, compatibility with solvents, and stability. Storage recommendations include maintaining it in a cool, dry place away from heat and light to preserve quality over an expected shelf life of 24 months or longer.
FAQ
What is citronellal / methyl anthranilate Schiff's base and what are its primary uses?
Citronellal / methyl anthranilate Schiff's base is a synthetic fragrance compound formed by chemically combining citronellal and methyl anthranilate. It is recognized for its citrus, woody, and slightly grassy odor profile, making it valuable in perfumery. Its use centers on providing fresh, natural-evoking scent notes in various fragrance applications, often serving as a replacement for natural oils such as palmarosa. It is predominantly incorporated as a perfuming agent in cosmetic and personal care formulations.
How is citronellal / methyl anthranilate Schiff's base typically used and where is it regulated?
This compound is used mainly as a fragrance ingredient incorporated at levels up to 2% in fragrance concentrates according to IFRA (Global) standards for safe use. It is not intended for flavoring purposes and lacks approvals for food use. The substance is handled as a synthetic fragrance material in cosmetic products, with usage and safety monitored by international bodies such as IFRA. Formulators apply it considering its physical properties to ensure stability and desirable olfactory effects while adhering to recommended exposure limits.
What safety and regulatory information is available for citronellal / methyl anthranilate Schiff's base?
Safety assessments report no classification for hazards under OSHA HCS (29 CFR 1910), indicating no identified pictograms or precautionary statements associated with this compound. However, producers and users adhere to IFRA's Code of Practice recommendations limiting usage to 2% in fragrances to manage potential sensitization risks. It is not approved for flavoring use and thus should not be included in food products. Storage guidelines advise keeping the compound sealed in a cool, dry environment away from heat and light to maintain stability. Various regulatory databases, including ECHA REACH pre-registrations and EPA registries, list the compound with CAS number 67845-42-5 for reference.
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 | citronellal / methyl anthranilate schiff's base |
| Trivial Name | Methyl 2-[(3,7-dimethyl-6-octen-1-ylidene)amino]benzoate |
| Short Description | citronama (IFF) |
| Formula | C18 H25 N O2 |
| CAS Number | 67845-42-5 |
| ECHA Number | 267-312-9 |
| FDA UNII | 686JW1W8W0 |
| Nikkaji Number | J287.479B |
| xLogP3-AA | 4.60 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 287.40264892578 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.367 to 8.433 |
| Refractive Index | 1.5125 to 1.5225 @ 20 °C |
| Boiling Point | 408 to 409°C @ 760 mm Hg |
| Flash Point TCC Value | 93.33 °C TCC |
| logP (o/w) | 7.08 est |
| 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, 0.2826 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Citrus | |
| fresh, citrus, weedy, grassy, sharp, woody | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 400 hour(s) at 100.00 % |
| General comment | At 10.00 % in dipropylene glycol. fresh citrus weedy grassy sharp woody |
Potential Uses
| Applications | |
| Odor purposes | Lily of the valley , Palmarosa oil replacer |
| 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: | |
| 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 / methyl anthranilate schiff's base usage levels up to: | |||
| 2.0000 % in the fragrance concentrate. | |||
| Recommendation for citronellal / methyl anthranilate schiff's base 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):67845-42-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :106871 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| methyl 2-(3,7-dimethyloct-6-enylideneamino)benzoate |
| Chemidplus:0067845425 |