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
Show more names
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
- Formal charge
- 0
- Complexity
- 179
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
- FLAVIS Number
- 9.73 · 09.730 | Ethyl cinnamate
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Liquid
- color
- Clear colorless to pale yellow
- Odor
- 100 % · at 100.00 %. sweet balsam fruity spicy powdery berry plum
- Odor Type
- balsamic
- biological source
- synthetic
- Water Solubility
- insoluble
- Merck
- 14 · 14,2299
- JECFA Number
- 659 · 659
- BRN
- 1238804 · 1238804
- Henry's Law Constant
- 2.3 · 2.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 5.3 · 5.3(19℃)
- Stability
- Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- UV ABSORBERPERFUMING
- InChI
- 1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
- InChIKey
- KBEBGUQPQBELIU-CMDGGOBGSA-N
- SMILES
- CCOC(=O)\C=C\c1ccccc1
- LogP
- 3.01 at · 3.01 at 23.6℃
- CAS DataBase Reference
- 103 · 103-36-6(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ETHYL CINNAMATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 23 P3M5JJ · C023P3M5JJ
- NIST Chemistry Reference
- trans-Ethyl cinnamate(103-36-6)
- EPA Substance Registry System
- Ethyl cinnamate (103-36-6)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 303 · H303
- Precautionary statements
- 270 · P270-P301+P312-P403-P501c
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Risk Statements
- 20 · 20-22
- Safety Statements
- 23 · 23-24/25
- WGK Germany
- 1 · 1
- RTECS
- 9010000 · GD9010000
- TSCA
- TSCA listed
- HS Code
- 29163990 · 29163990
- Storage Class
- 10 · 10 - Combustible liquids
- Toxicity
- 50 value · 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).
- REACH Registrations
- Active
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).
- risk_code
- 20-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H303
- REACH Registrations
- Active
- Precautionary statements
- P270-P301+P312-P403-P501c
Chemistry & industry
Applications
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
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Ethyl cinnamate is an alkyl cinnamate and an ethyl ester.
Related reactions
Linked notes
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