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methyl cinnamate
Methyl cinnamate is an ester of cinnamic acid with a balsamic, spicy aroma used as a flavor and fragrance agent, naturally found in cinnamon and basil.
General Material Description
Methyl cinnamate is a pure odor and flavor compound classified chemically as an ester with the molecular formula C10H10O2. It typically appears as a clear liquid with a characteristic balsamic and spicy aroma reminiscent of cinnamon and strawberry. Known also by several synonyms including cinnamic acid methyl ester and methyl 3-phenylpropenoate, methyl cinnamate is listed in chemical databases like PubChem. This compound is naturally extracted from essential oils such as cinnamon bark, basil leaf, and bay laurel fruit. It serves mainly as a flavoring and perfuming agent in various commercial applications due to its distinctive aroma and flavor properties.
Occurrence, Applicability & Potential Uses
Methyl cinnamate occurs naturally in various plants and their extracts, including cinnamon bark, basil leaf and oil, bay laurel fruit oil, and other botanicals such as champaca and jasmine absolutes. It features prominently in the fragrance industry as a balsamic and spicy note, often substituting for basil oil. In flavor applications, it imparts sweet, fruity, and spicy accents and can be used to evoke notes of strawberry, cherry, and vanilla. This compound is regulated by FEMA (US) as number 2698, and by IFRA (Global) guidelines for fragrance use, which recommend usage levels to ensure safety. The compound is also classified under REACH (EU) regulations, emphasizing its controlled application in consumer products.
Physico-Chemical Properties Summary
Methyl cinnamate is a moderately volatile ester with a boiling point range of 260 to 262°C at standard atmospheric pressure (760 mm Hg) and 164 to 165°C at reduced pressure (50 mm Hg). It has a molecular weight of approximately 162.19 g/mol and a log P value of 2.62, indicating moderate lipophilicity. Its flash point is about 141°C (286°F), suggesting it is relatively stable under normal handling conditions. The compound exhibits low vapor pressure at room temperature (0.011 mmHg at 25°C), which contributes to its lingering odor profile. Solubility tests show it dissolves in alcohols, dipropylene glycol, fixed oils, paraffin oil, and is sparingly soluble in water (around 387 mg/L at 25°C). It maintains stability in various matrices, including creams, shampoos, and bath foams, without significant discoloration or degradation, making it suitable for diverse formulation purposes.
FAQ
What is methyl cinnamate and what are its primary characteristics?
Methyl cinnamate is an ester derived from cinnamic acid with the chemical formula C10H10O2. It exhibits a balsamic, spicy aroma that is often described as sweet with fruity undertones reminiscent of strawberry and cinnamon. It commonly appears as a clear liquid used as a flavor and fragrance agent. The compound naturally occurs in several plant sources including cinnamon and basil. It is also recognized by various synonyms such as cinnamic acid methyl ester and methyl 3-phenylpropenoate.
Where does methyl cinnamate naturally occur and how is it typically used?
Methyl cinnamate is found in nature within essential oils extracted from plants such as cinnamon bark, basil leaves, bay laurel fruit, and various floral absolutes like jasmine and narcissus. It is widely employed in the fragrance industry to impart spicy, balsamic, and fruity notes, often serving as a basil oil substitute. Additionally, it is used in flavor applications to add sweet, fruity, and warm spicy characteristics to products. Its compatibility with multiple solvents and stability in cosmetic formulations like creams and shampoos expand its utility in consumer product manufacturing.
What regulations apply to methyl cinnamate and how is it sourced for commercial use?
Methyl cinnamate is regulated under FEMA (US) as FEMA number 2698 and is subject to the IFRA (Global) Code of Practice, which provides guidelines on safe maximum levels in fragranced products. It is also covered by REACH regulations within the European Union. Commercially, it is sourced by extraction from natural essential oils or can be synthesized chemically to meet flavor and fragrance industry standards. Its inclusion in the Food Chemical Codex and FEMA GRAS list underscores its approval as a flavoring substance within defined use levels. Safety assessments detail its irritant potential and establish precautions for handling in manufacturing environments.
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 |
Literature & References
| methyl 3-phenylprop-2-enoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 103-26-4 |
| Pubchem (cid): | 7644 |
| Pubchem (sid): | 134971915 |
| Flavornet: | 103-26-4 |
| Pherobase: | View |
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 |
| CHEMBL: | View |
| KEGG (GenomeNet): | C06358 |
| HMDB (The Human Metabolome Database): | HMDB33833 |
| FooDB: | FDB012001 |
| YMDB (Yeast Metabolome Database): | YMDB01744 |
| Export Tariff Code: | 2916.39.7900 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Trivial Name | methyl cinnamate |
| Short Description | cinnamic acid methyl ester |
| Formula | C10 H10 O2 |
| CAS Number | 103-26-4 |
| FEMA Number | 2698 |
| Flavis Number | 9.74 |
| ECHA Number | 203-093-8 |
| FDA UNII | 533CV2ZCQL |
| Beilstein Number | 0386468 |
| MDL | MFCD00008458 |
| COE Number | 333 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 658 methyl cinnamate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 103-26-4 ; METHYL CINNAMATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 162.18809509277 |
| Boiling Point | 260 to 262°C @ 760 mm Hg |
| Boiling Point | 164 to 165°C @ 50 mm Hg |
| Acid Value | 2 max KOH/g |
| Vapor Pressure | 0.011 mmHg @ 25 °C |
| Flash Point TCC Value | 141.11 °C TCC |
| logP (o/w) | 2.62 |
| Solubility | |
| alcohol | Yes |
| dipropylene glycol | Yes |
| fixed oils | Yes |
| paraffin oil | Yes |
| water, 387.1 mg/L @ 25 °C (est) | Yes |
| Stability | |
| bath foam | Unspecified |
| cream | Unspecified |
| hair spray | Unspecified |
| non-discoloring in most media | Unspecified |
| powder | Unspecified |
| shampoo | Unspecified |
Organoleptic Properties
| Odor Type: Balsamic | |
| sweet, balsamic, strawberry, cherry, cinnamyl | |
| Odor strength | medium |
| Substantivity | 164 hour(s) at 100.00 % |
| Luebke, William tgsc, (1983) | At 100.00 %. sweet balsam strawberry cherry cinnamon |
| Flavor Type: Spicy | |
| cinnamyl, balsamic, spicy, fruity, mango, papaya, cherry | |
| Luebke, William tgsc, (1983) | Cinnamyl balsamic spicy fruity mango papaya cherry |
| Useful in: vanilla, fruity red, fruity yellow, fruity tropical. | Cinnamon, sweet, balsamic, heavy-fruity, strawberry |
| General comment | Sweet, strawberry |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Amber , Balsam , Basil oil replacer , Blackberry , Butter , Carnation , Cherry , Cherry blossom , Currant , Galangal root , Honeysuckle , Incense , Jasmin , Lavender , Lilac , Mulberry , Musk , Narcissus , Oriental , Peach , Pepper , Plum , Raspberry , Rose , Spice , Strawberry , Tobacco , Vanilla , Wisteria , Woody |
| Flavoring purposes | Galangal root |
| Other purposes | Fixer , Origan |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. 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) | |
| Acute toxicity, Oral (Category 4), H302 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |  |
| Signal word | Warning |
| Hazard statement(s) | |
| H302 - Harmful if swallowed | |
| Precautionary statement(s) | |
| P264 - Wash skin thouroughly after handling. P270 - Do not eat, drink or smoke when using this product. P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P330 - Rinse mouth. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Human Experience: | |
| 10 % solution no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 [sex: M,F] 2610 mg/kg Confidence limits of 2000-3410 mg/kg bw, 6 doses up to 6000 mg/kg bw) were given to groups of 5 M and 5 F. (Wong & Weir, 1971b) oral-rat LD50 2610 mg/kg Food and Cosmetics Toxicology. Vol. 13, Pg. 849, 1975. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 13, Pg. 849, 1975. | |
| 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: | |||
| 0.3100 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001) | |||
| Recommendation for methyl cinnamate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 0.2100 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.0054 mg/kg/day (IFRA, 2001) | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 2400.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 830.00 (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: | - | 13.00000 | |
| beverages(nonalcoholic): | - | 1.90000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 2.70000 | 40.00000 | |
| condiments / relishes: | - | 0.40000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 3.80000 | |
| fruit ices: | - | 3.80000 | |
| gelatins / puddings: | 1.70000 | 14.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 8.70000 | |
| 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 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) 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 |
| Safety and efficacy of aryl-substituted primary alcohol, aldehyde, acid, ester and acetal derivatives belonging to chemical group 22 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):103-26-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7644 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| methyl 3-phenylprop-2-enoate |
| Chemidplus:0000103264 |
| RTECS:GE0190000 for cas# 103-26-4 |