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Ethyl cinnamate

CAS No.103-36-6
Chemical Name:Ethyl cinnamate
CBNumber:CB9226049
Molecular Formula:C11H12O2
Formula Weight:176.21
MOL File:103-36-6.mol

Ethyl cinnamate Property

Melting point 6-8 °C (lit.)
Boiling point 271 °C (lit.)
Density 1.049 g/mL at 20 °C (lit.)
vapor pressure 6Pa at 20℃
FEMA 2430 | ETHYL CINNAMATE
refractive index n20/D 1.558(lit.)
Flash point >230 °F
storage temp. 2-8°C
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form Liquid
color Clear colorless to pale yellow
Odor at 100.00 %. sweet balsam fruity spicy powdery berry plum
Odor Type balsamic
biological source synthetic
Water Solubility insoluble
Merck 14,2299
JECFA Number 659
BRN 1238804
Dielectric constant 5.3（19℃）
Stability Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.
LogP 3.01 at 23.6℃
CAS DataBase Reference 103-36-6(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) ETHYL CINNAMATE
FDA 21 CFR 172.515
EWG's Food Scores 1
FDA UNII C023P3M5JJ
NIST Chemistry Reference trans-Ethyl cinnamate(103-36-6)
EPA Substance Registry System Ethyl cinnamate (103-36-6)
UNSPSC Code 85151701
NACRES NA.24

Safety

Risk Statements :20-22
Safety Statements :23-24/25
WGK Germany :1
RTECS :GD9010000
TSCA :Yes
HS Code :29163990
Toxicity :The acute oral LD₅₀ value in rats was reported as 7.8 g/kg (7.41-8.19 g/kg) (Russell, 1973). The acute dermal LD₅₀ value in rabbits was reported as > 5 g/kg (Russell, 1973).

NFPA 704:

	0
0		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H303
Precautionary statements P270-P301+P312-P403-P501c

Ethyl cinnamate Price More Price(12)

Brand: Sigma-Aldrich(India)
Product number: W243019
Product name : Ethyl cinnamate
Purity: natural, ≥95%, FG
Packaging: 1SAMPLE-K
Price: ₹5347.55
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: W243019
Product name : Ethyl cinnamate
Purity: natural, ≥95%, FG
Packaging: 100G
Price: ₹9038.88
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: W243019
Product name : Ethyl cinnamate
Purity: natural, ≥95%, FG
Packaging: 1KG
Price: ₹45540.78
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W243019
Product name : Ethyl cinnamate
Purity: natural, ≥95%, FG
Packaging: 5KG
Price: ₹199169.18
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W243000
Product name : Ethyl cinnamate
Purity: ≥98%, stabilized, FCC, FG
Packaging: 1SAMPLE-K
Price: ₹5141.88
Updated: 2022/06/14
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Ethyl cinnamate Chemical Properties,Usage,Production

Description Ethyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
Chemical Properties Ethyl Cinnamate, ethyl 3-phenylacrylate, C6H5CH=CHCOOC2H5.Occurs naturally in storax and the volatile oil of Koempferia galanga.The commercial product is a colourless liquid, invariably prepared artificially. Has a sweet balsami honey-note odor of great persistence. Ethyl cinnamate is useful in Oriental bouquets, and in combination with clary sage and citrus oils will make delightful amber colognes.
Occurrence Normally 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.
Uses Ethyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.
Production Methods Ethyl 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 .
Preparation By 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
Definition ChEBI: Ethyl cinnamate is an alkyl cinnamate and an ethyl ester.
Aroma threshold values Detection: 17 to 40 ppb
Taste threshold values Taste 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
General Description Ethyl cinnamate can be used as a flavoring and fragrance ingredient. It is one of the key odor components reported in Burgundy Pinot noir wines.
Biochem/physiol Actions Ethyl cinnamate inhibits the growth of Chlorella pyrenoidosa.
Safety Profile Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS
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.]