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linalyl cinnamate
Linalyl cinnamate is a cinnamic acid ester known for its balsamic odor and fruity flavor, commonly used in fragrances and flavorings as a perfuming agent and fixer.
General Material Description
Linalyl cinnamate is a synthetic ester formed from cinnamic acid and linalool-derived alcohol. It appears as a colorless to pale yellow liquid with a molecular formula of C19H24O2. The compound is recognized for its balsamic odor with sweet, lily, neroli, labdanum, amber nuances and a fruity, tropical berry flavor profile. It is also known by multiple synonyms including 'cinnamic acid linalyl ester' and '3,7-dimethylocta-1,6-dien-3-yl cinnamate'. It is commonly utilized in flavor and fragrance formulations and is documented in chemical databases such as PubChem. Linalyl cinnamate is produced by esterification processes and can be sourced industrially for use in perfumes and flavorings.
Occurrence, Applicability & Potential Uses
Although linalyl cinnamate does not naturally occur in significant amounts in biological systems, it is widely applied in the fragrance and flavor industry. It imparts nuanced balsamic, floral, and fruity notes that are valuable in perfumery to evoke orange blossom, neroli, jasmine, lavender, rose, and woody accords. It acts as a fixer, enhancing the lasting power of fragrances. Linalyl cinnamate is supported by regulatory standards such as FEMA (US), where it holds FEMA number 2641, indicating its acceptance as a safe flavoring substance under specified use levels. Its usage extends to cosmetic perfuming agents, emphasizing its functional versatility in aroma formulations.
Physico-Chemical Properties Summary
Linalyl cinnamate is a moderately lipophilic ester with an estimated octanol-water partition coefficient (log P) of approximately 5.6, indicating substantial hydrophobic character. It exhibits low vapor pressure near 1.0E-6 mmHg at 25 °C, contributing to its notable substantivity in fragrance applications, with a lasting time around 132 hours at full concentration. The compound is soluble in alcohol solvents and sparingly soluble in water, with experimental solubility approximately 4 mg/L at 20 °C. Its flash point is relatively high at 100 °C (212 °F), signaling caution in handling combustible materials. These properties influence its formulation characteristics, favoring oil- or ethanol-based delivery systems in flavor and fragrance applications.
FAQ
What is linalyl cinnamate and what are its main properties?
Linalyl cinnamate is an ester derived from cinnamic acid and linalool-related alcohol. It is a colorless to pale yellow liquid used primarily for its balsamic and fruity odor and flavor. Known for enhancing floral and woody notes, it serves as a perfuming agent and a fixer in various formulations. Chemically, it has the formula C19H24O2 and shows low volatility, considerable lipophilicity, and limited water solubility, characteristics that support its stability and lasting effect in scents and flavors.
How is linalyl cinnamate used, and where is it typically found?
Linalyl cinnamate is extensively used in the fragrance industry to create complex floral and balsamic accords reminiscent of orange blossom, jasmine, and neroli. It functions as a fixer, prolonging scent longevity in perfumes and cosmetic products. Additionally, it finds application as a flavoring agent in foods and beverages, approved for use under regulated amounts. Although it is synthetic, it mimics natural aromatic profiles, making it valuable in both fine fragrances and flavor formulations.
What regulations and safety considerations apply to linalyl cinnamate?
Linalyl cinnamate is recognized by FEMA (Flavor and Extract Manufacturers Association, US) with FEMA number 2641, indicating it is generally accepted as safe when used within established limits. It is included in IFRA (International Fragrance Association) standards specifying maximum use levels in cosmetics and fine fragrances to ensure consumer safety. Safety assessments report low toxicity with no significant irritation or sensitization at typical concentrations. Compliance with REACH (EU) requirements and adherence to good manufacturing practices further ensure its safe application in consumer products.
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): | HMDB30432 |
| FooDB: | FDB002296 |
| Export Tariff Code: | 2916.12.6000 |
| ChemSpider: | View |
General Material Information
| Preferred name | linalyl cinnamate |
| Trivial Name | Linalyl cinnamate |
| Short Description | cinnamic acid, linalyl ester |
| Formula | C19 H24 O2 |
| CAS Number | 78-37-5 |
| FEMA Number | 2641 |
| Flavis Number | 9.736 |
| ECHA Number | 201-110-3 |
| FDA UNII | 5E73T3S69W |
| Nikkaji Number | J9.830B |
| Beilstein Number | 3140688 |
| MDL | MFCD00048303 |
| COE Number | 329 |
| xLogP3-AA | 5.40 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 668 linalyl cinnamate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 78-37-5 ; LINALYL CINNAMATE |
| Synonyms |
|
Suppliers
| BOC Sciences | Givaudan |
| Lluch Essence | Pell Wall Perfumes |
| Penta International | R C Treatt & Co Ltd |
| Sigma-Aldrich: Aldrich | Vigon International |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 284.39868164062 |
| Vapor Pressure | 1.0E-6 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 5.62 est |
| Solubility | |
| alcohol | Yes |
| water, 4 mg/L @ 20 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Balsamic | |
| sweet, balsamic, lily, neroli, labdanum, amber | |
| Odor strength | medium |
| Substantivity | 132 hour(s) at 100.00 % |
| Luebke, William tgsc, (1996) | At 100.00 %. sweet balsam lily neroli labdanum amber |
| Flavor Type: Fruity | |
| fruity, tropical, berry, balsamic, cinnamon, spicy | |
| Luebke, William tgsc, (1996) | Sweet fruity tropical berry balsamic cinnamon spicy |
Potential Uses
| Applications | |
| Odor purposes | Amber , Balsam , Champaca , Freesia , Jasmin , Labdanum , Lavender , Lily , Lotus , Magnolia , Neroli , Orange blossom , Oriental , Rose , Tuberose , Woody |
| Other purposes | Fixer |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. | |
| 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. | |
| Human Experience: | |
| 8 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| gavage-rat LD50 [sex: M,F] 9960 mg/kg Published study. Confidence limits of 8230-12050 mg/kg bw, groups of 5 M and 5 F. (Jenner et al., 1964) oral-rat LD50 9960 mg/kg Food and Cosmetics Toxicology. Vol. 14, Pg. 463, 1976. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 14, Pg. 463, 1976. | |
| 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 | |||
| maximum skin levels for fine fragrances: | |||
| 0.4200 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2002) | |||
| Recommendation for linalyl cinnamate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 1.0500 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.0268 mg/kg/day (IFRA, 2002) | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 6.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 3.00 (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.10000 | |
| beverages(nonalcoholic): | - | 0.57000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.59000 | |
| fruit ices: | - | 0.59000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 2.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 68 (FGE.68): Consideration of cinnamyl alcohol and related flavouring agents evaluated by JECFA (55th meeting) evaluated by EFSA in FGE.15Rev1 (2008) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):78-37-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5355858 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3,7-dimethylocta-1,6-dien-3-yl (E)-3-phenylprop-2-enoate |
| Chemidplus:0000078375 |