ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Carboxylic acids and esters > Aromatic carboxylic acid ester > Ethyl cinnamate
Basic information Application of spices and fragrance Content analysis Toxicity Use the limit Maximal allowable amount as additive and maximal allowable residue Chemical properties Uses Production method Safety Related Supplier
Ethyl cinnamate Chemical Properties
- Melting point:6-8 °C (lit.)
- Boiling point:271 °C (lit.)
- Density 1.049 g/mL at 20 °C (lit.)
- FEMA 2430 | ETHYL CINNAMATE
- refractive index n
- Flash point:>230 °F
- storage temp. Refrigerator (+4°C)
- form Liquid
- color Clear colorless to pale yellow
- Water Solubility insoluble
- Merck 14,2299
- JECFA Number659
- BRN 1238804
- Stability:Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.
- CAS DataBase Reference103-36-6(CAS DataBase Reference)
- NIST Chemistry Referencetrans-Ethyl cinnamate(103-36-6)
- EPA Substance Registry SystemEthyl cinnamate (103-36-6)
Ethyl cinnamate Usage And Synthesis
- Application of spices and fragranceEthyl cinnamate is also known as β-phenyl acrylate and ethyl 3-phenylpropionate. At room temperature, it appears as colorless oily liquid. It is naturally presented in guava, strawberries, white and red wine, brandy, rum, vanilla and prickly pear. Aroma characterization: sweet amber cream, sweet orange and grape-like rhyme with elegant fragrance of balsam and honey-fragrance. Flavor: strong sweet fruit, plum, cherry-like scent, sweet fruit flavor, fragrance incense, berries, mixed sweet drinks, green incense with vanilla fragrant orchid fragrance. It can be used for the formulation of edible fragrance of almond, vanilla, cinnamon, honey, berries, mixed sweet drinks, fragrance flavor, spicy type, grape and cherry flavors.
- Content analysisAs determined by the determination method 1 in the ester assay (OT-18). The amount of taken sample was 1.2 g. The equivalent factor (e) in the calculation is taken as 88.11.
It can be alternatively determined by polar column method in GT-10-4.
- ToxicityADI 1.25 mg/kg (CE).
LD50: 4000 m/kg (rat, oral administration).
- Use the limitFEMA (mg/kg): soft drinks 4.1; cold drinks 8.8; candy 9.5; baked goods 12; pudding 2.4; gum 1l~40.
Appropriate amount should be the limitation (FDA § 172.515, 2000).
- Maximal allowable amount as additive and maximal allowable residue▼▲Name of additiveFood allowed to use it as additivesFunction of additiveMaximal allowable residue（g/kg）Maximal allowable residue（g/kg）Ethyl cinnamateFoodEdible spiceSpices used for the formulation of fragrance should not exceed the maximal allowable amount and maximal allowable residue provided in GB2760/
- Chemical propertiesIt appears as nearly colorless, transparent oily liquid with light, long lasting cinnamon and strawberry aroma and sweet honey aroma. It has no optical activity with the melting point of 12 ° C, the boiling point of 272 ° C and the flash point of 93.5 ° C. It is miscible in ethanol, ether and most non-volatile oils. It is almost insoluble in glycerol and water. It is slightly soluble in propylene glycol.
Its natural product exists in the Soviet Union balsam, galangal oil and so on.
- Uses1. GB 2760-96 provides it as food spices allowable for temporary use. It is mainly used for the preparation of strawberry, raspberry and plum, cherry and other type of flavor. Owing to the high boiling point and stability, it is appropriate to be used for baked goods.
2. It is an important kind of fragrance and spices intermediates. It can also be used as the intermediates of medicine and food additives.
3. It can be used for the perfume industry.
4. It is suitable to be applied to the roses, daffodils, ambergris-amber, citrus incense, fern, chypre, Cologne, re-oriental and woody-incense and other flavor. It can be used to coordinate the other ointment in the soap, toiletries water and powder flavor and also has incense fixative effect. It can also be used as flavoring agent to be applied to flavor such as cherry, grape, strawberry, raspberry, peach, plum, cinnamon, spicy and vanilla bean.
5. It can be used as the incense fixative agent and modification agents for fragrance. It can also be applied to glass prism
6. This product exists in the natural storax with a fruit-like aroma and the atmosphere being clear and sweet with oriental fragrance. It has excellent effect when being used in combination with the natural fruit essential oils with the effect being better for fragrance, perfume and flavor. It can also be used in edible waxberry essence.
- Production methodIt can be obtained through the esterification between cinnamic acid and ethanol in the presence of sulfuric acid with a yield of about 60%. It can also be derived through the reaction bewteen benzaldehyde and ethyl acetate.
It can be obtained through the reaction between benzaldehyde and ethyl acetate in the presence of sodium metal.
It is derived from the heating of cinnamic acid, ethanol and sulfuric acid to 100 °C in the presence of aluminum sulfate.
- DescriptionEthyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon. Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note".
The p-methoxy derivative is reported to be a mono amine oxidase inhibitor.
- Chemical PropertiesEthyl cinnamate has a sweet balsami honey-note odor.
- Chemical Propertiescolourless liquid
- OccurrenceNormally occurring in the trans-form; a cis-form also exists. Reported found in Oriental styrax, in the oil of Campheria galanga and in the rhizomes of Hedychium spicatum. Also reported found in cherry, American cranberry, pineapple, guava, strawberry, fresh blackberry, strawberry jam, soybean, yellow passion fruit juice, hybrid passion fruit juice, apple brandy, quince, prickly pear, strawberry wine, Bourbon vanilla, sea buckthorn, cinnamon leaf and root bark, clove, brandy, rum, sherry, grape wines, cocoa, soybean and other natural sources.
- UsesPerfumery, flavoring extracts.
- Production MethodsEthyl cinnamate is found in storax oil, Kaempferia galanga, and several other oils. It is produced by the direct esterification esterification of ethanol with cinnamic acid under azeotropic conditions or by Claisen-type condensation of ethyl acetate and benzaldeyde in the presence of sodium metal .
- PreparationBy heating to 100°C cinnamic acid, alcohol and sulfuric acid in the presence of aluminum sulfate; also by Claisen condensation of benzaldehyde and ethyl acetate
- Aroma threshold valuesDetection: 17 to 40 ppb
- Taste threshold valuesTaste characteristics at 20 ppm: balsamic, powdery, fruity, berry, punch, spice, sweet and green.
- Synthesis Reference(s)Journal of the American Chemical Society, 110, p. 2655, 1988 DOI: 10.1021/ja00216a053
Tetrahedron Letters, 30, p. 5153, 1989 DOI: 10.1016/S0040-4039(01)93472-0
- Safety ProfileModerately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS
- Purification MethodsWash the ester with aqueous 10% Na2CO3, then water, dry (MgSO4), and distil it. The purified ester is saponified with aqueous KOH, and, after acidifying the solution, cinnamic acid is isolated, washed and dried. The ester is reformed by refluxing for 15hours the cinnamic acid (25g) with absolute EtOH (23g), conc H2SO4 (4g) and dry *benzene (100mL), after which it is isolated, washed, dried and distilled under reduced pressure [Jeffery & Vogel J Chem Soc 658 1958]. [Beilstein 9 IV 2006.]
Ethyl cinnamate Preparation Products And Raw materials
- Isopropyl myristate Benzyl cinnamate Myristic acid TRIMYRISTIN (aR)-alpha-[(1S)-1-[2,6-Dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-4-hydroxy-3-methoxybenzenemethanol MONOMYRISTIN Cinnamyl alcohol Cinnamic acid PHENYL RESIN Propyl cinnamate CINNAMATE Ethyl acetate Ethanol Octyl 4-methoxycinnamate Trinexapac-ethyl Ethyl formate Ethyl propionate 2-Ethoxyethanol
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