Ethyl 3-phenylprop-2-enoate

HCID 7649CAS 103-36-6

Basic information

Standard SMILES
CCOC(=O)C=Cc1ccccc1
InChIKey
KBEBGUQPQBELIU-UHFFFAOYSA-N
Molecular formula
C11H12O2
Average molar mass
176.21 g/mol
Monoisotopic mass
176.08372962

Overview

ethyl (E/Z)-cinnamate has been reported in Mandragora autumnalis, Kaempferia galanga, and other organisms with data available.

Names & identifiers

Preferred name
Ethyl 3-phenylprop-2-enoate
IUPAC
ethyl 3-phenylprop-2-enoate
English name
Ethyl cinnamate
Molecular formula
C11H12O2
Molecular weight
176.21

Names & synonyms

Ethyl 3-phenylprop-2-enoateRefChem:1084880Ethyl 3-phenylacrylateethyl-(E)-cinnamate,ethyl-trans-cinnamate2-Propenoic acid, 3-phenyl-, ethyl ester, (2Z)-cis-Ethyl Cinnamate (contains up to 10% Ethyl dihydrocinnamateSCHEMBL112446orb1297381orb1940114orb3025570SCHEMBL1556354SCHEMBL3348480
Show more names
CINNAMIC ACID ETHYL ESTER2-Propenoic acid, 3-phenyl-, ethyl esterFEMA 2430EthylphenylacryateETHYL TRANS-CINNAMATEEthyl 3-phenyl-2-propenoateEthyl (E)-3-phenylprop-2-enoateethyl (2E)-3-phenylprop-2-enoateNSC 6773
SCHEMBL9024482SCHEMBL9869478SCHEMBL9869485CHEMBL3182745SCHEMBL11372177SCHEMBL11372184SCHEMBL11533016Cinnamic acid, ethyl ester (6CI,7CI,8CI); 3-Phenyl-2-propenoic acid ethyl ester

Database identifiers

CAS
103-36-6
PubChem CID
7649
DTXSID
DTXSID9022520
ChEMBL
CHEMBL3182745

Properties

Computed structural properties

XLogP
3
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
13

Physicochemical properties

Melting point
6 · 6-8 °C (lit.)
Boiling point
271 °C · 271 °C (lit.)
Density
1.049 g/mL · 1.049 g/mL at 20 °C (lit.)
vapor pressure
6 Pa · 6Pa at 20℃
refractive index
20 · n20/D 1.558(lit.)
FEMA
2430 · 2430 | ETHYL CINNAMATE

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
1
tsca
TSCA listed
rtecs
GD9010000
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).

Chemistry & industry

Applications · 4 items

DescriptionEthyl 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.

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.

UsesEthyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.

General DescriptionEthyl cinnamate can be used as a flavoring and fragrance ingredient. It is one of the key odor components reported in Burgundy Pinot noir wines.

Preparation methods

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]

Additional notes

DefinitionChEBI: Ethyl cinnamate is an alkyl cinnamate and an ethyl ester.

Related reactions

64 records

Linked notes

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