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Ethyl cinnamate

CAS：103-36-6
MW:176.215
MF：C11H12O2

Ethyl 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. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Ethyl cinnamate

1.2 Synonyms: 2-Propenoic acid, 3-phenyl-, ethyl ester, (2E)-; 2-Propenoic acid, 3-phenyl-, ethyl ester, (E)-; 3-phenylacrylic acid ethyl ester; Cinnamic Acid Ethyl Ester; EINECS 203-104-6; Ethyl (2E)-3-phenyl-2-propenoate; Ethyl (2E)-3-phenylacrylate; ethyl (2E)-3-phenylprop-2-enoate; ethyl 3-phenyl-2-propenoate; ethyl 3-phenylacrylate; Ethyl ciamate; Ethyl Cinnamate Trans; ethyl dihydrocinnamate; Ethyl Gui; Ethyl trans-3-Phenylacrylate; ETHYL TRANS-CINNAMATE; Ethylcinnamat; Ethylphenylacryate; FEMA 2430; MFCD00009189; RARECHEM AL BI 0143; trans-3-Phenylacrylic Acid Ethyl Ester; TRANS-ETHYLCINNAMATE; Zimtsaeureethylester;

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1.3 CAS No.: 103-36-6

1.4 CID: 637758

1.5 EINECS: 203-104-6

1.6 Molecular Formula: C11H12O2

1.7 Inchi: InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+

1.8 InChkey: KBEBGUQPQBELIU-CMDGGOBGSA-N

1.9 Canonical Smiles: CCOC(=O)C=CC1=CC=CC=C1

1.10 Isomers Smiles: CCOC(=O)/C=C/C1=CC=CC=C1

2. Properties

2.1 Appearance: Clear colorless to pale yellow Liquid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: It 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.

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2.4 Color/Form: Oil

2.5 Water Solubility: H2O: insoluble

2.6 Stability: Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.

2.7 StorageTemp: Refrigerator (+4°C)

3. Use and Manufacturing

3.1 Description: Ethyl cinnamate (CAS 103-36-6) is a colorless to pale yellow liquid with a sweet, fruity odor. It has a basic structure consisting of an ethyl group attached to a cinnamate group. This chemical is soluble in alcohol and oils, but only slightly soluble in water. Ethyl cinnamate has a melting point of -8°C and a boiling point of 271°C. It is stable under normal conditions and does not undergo any significant decomposition. However, it may react with strong oxidizing agents.

Applicable Fields
Perfume Industry: Ethyl cinnamate is widely used in the perfume industry as a fragrance ingredient. It provides a sweet, fruity scent and is often used in floral and fruity fragrances. The mechanism of action involves the interaction of the chemical with olfactory receptors in the nose, resulting in the perception of a pleasant fragrance.

Food Industry: In the food industry, ethyl cinnamate is used as a flavoring agent. It imparts a fruity and sweet taste to various food products, including candies, baked goods, and beverages. The mechanism of action involves stimulating taste receptors on the tongue, enhancing the perception of sweetness.

Pharmaceutical Industry: Ethyl cinnamate has potential applications in the pharmaceutical industry. It exhibits antimicrobial and antioxidant properties, making it suitable for use in topical formulations and as a preservative. The mechanism of action involves inhibiting the growth of microorganisms and preventing oxidative damage.

Storage Conditions
Store in a cool, dry place.

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3.2 Methods of Manufacturing: Benzaldehyde and ethyl acetate are compounded in the presence of sodium metal. By cinnamic acid, ethanol, sulfuric acid in the presence of aluminum sulfate heated to 100 ℃ derived.

3.3 Produe Method: Ethyl cinnamate is found in storax oil, Kaempferia galanga,and several other oils. It is produced by the direct esterification esterificationof ethanol with cinnamic acid under azeotropic conditionsor by Claisen-type condensation of ethyl acetate andbenzaldeyde in the presence of sodium metal .

3.4 Purification Methods: Wash 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 Raw materials

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3.5 Usage: 1. 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 prism6. 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.

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4. Safety and Handling

4.1 Safety Profile: Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Risk Statements: 20-22
R20:Harmful by inhalation.?
R22:Harmful if swallowed.
Safety Statements: 23-24/25
S23:Do not breathe vapour.?
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: GD9010000

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4.4 Specification: ? Ethyl 3-phenyl propenoate , with CAS number of 103-36-6, can be called (2E)-3-Phénylacrylate d'éthyle ; (Z)-Ethyl cinnamate ; 2-propenoic acid, 3-phenyl-, ethyl ester ; 2-propenoic acid, 3-phenyl-, ethyl ester, (2E)- ; 2-Propenoic acid, 3-phenyl-, ethyl ester, (E)- ; Ethyl (2E)-3-phenyl-2-propenoate ; Ethyl (2E)-3-phenylacrylate ; ethyl (2E)-3-phenylprop-2-enoate . It is a?colourless liquid.

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4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	4gm/kg (4000mg/kg)	?	Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.
mouse	LD50	oral	4gm/kg (4000mg/kg)	?	Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)	?	Food and Cosmetics Toxicology. Vol. 12, Pg. 719, 1974.
rat	LD50	oral	4gm/kg (4000mg/kg)	?	Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

103-36-6Total: 104 Synthesis Route

621-82-9 232 Suppliers

103-36-6 178 Suppliers

100-52-7 232 Suppliers

103-36-6 178 Suppliers

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8. Precursor and Product

precursor:

100-52-7

5292-53-5

5464-70-0

3646-50-2

621-82-9

121-39-1

2216-94-6

103-26-4

607-81-8

104-55-2

product:

122-57-6

2021-28-5

5464-70-0

621-82-9

121-39-1

104-54-1

122-97-4

621-79-4

827-42-9

104-55-2

9. Computed Properties

Molecular Weight：176.215g/mol
Molecular Formula：C₁₁H₁₂O₂
Compound Is Canonicalized：True
XLogP3-AA：176.083729621
Monoisotopic Mass：176.083729621
Complexity：179
Rotatable Bond Count：4
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：2
Topological Polar Surface Area：26.3
Heavy Atom Count：：13
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：1
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADACgmAIyCIAABACIAiDSCAACAAAgAAAIiAAAAMgIJCKAMRCCMAAggAAIqYcAgAAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Ethyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.

Storage Conditions: Benzaldehyde and ethyl acetate are compounded in the presence of sodium metal. By cinnamic acid, ethanol, sulfuric acid in the presence of aluminum sulfate heated to 100 ℃ derived.

Production: < 25,000 lb

Manufacturing Info: 2-Propenoic acid, 3-phenyl-, ethyl ester: ACTIVE

11. Toltal 162 Suppliers View more

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12. Related Questions

: What are the uses of ethyl cinnamate Introduction: Ethyl Cinnamate is an organic compound with a sweet aroma, which is widely used in multiple fields. Its aromatherapy makes it an important ingredient in food fragrance, perfume and cosm..; What are the synthesis methods of ETHYL CINNAMATE Introduction: ETHYL CINNAMATE, also known as β-phenyl acrylic ethyl. It is an important spice and food additive with the aroma and heritage of sweet orange and grapes, and the aroma is lasting. It i..; What are the harm of ETHYL CINNAMATE Introduction: ETHYL CINNAMATE is a common organic compound that exists in natural fruits, spices and essential oils. It is also commonly used in food additives, spices and cosmetics. However, in rece..; What is Ethyl Cinnamate Summary: ETHYL CINNAMATE is an organic compound. The chemical formula is C11H12O2. It is a ester -based substance generated by cinnamonic acid and ethanol through esters. It has a sweet aroma, simila..

13. Realated Product Infomation