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| CAS No.: | 104-55-2 |
|---|---|
| Name: | Cinnamaldehyde |
| Article Data: | 711 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H8O |
| Molecular Weight: | 132.162 |
| Synonyms: | 2-Propenal,3-phenyl-;3-Phenyl-2-propen-1-al;3-Phenyl-2-propenal;3-Phenyl-2-propenaldehyde;3-Phenyl-2-propene-1-al;3-Phenylacrolein;3-Phenylacrylaldehyde;3-Phenylpropenal;Abion CA;Benzylideneacetaldehyde;Cassia aldehyde;Cinnacure;Cinnamal;Cinnamic aldehyde;Cinnamite;Cinnamyl aldehyde;NSC16935;NSC 40346;Phenylacrolein;Zimtaldehyde;b-Phenylacrolein;Cinnamaldehyde/cinnamic aldehyde; |
| EINECS: | 203-213-9 |
| Density: | 1.034 g/cm3 |
| Melting Point: | -9 - -4 °C(lit.) |
| Boiling Point: | 246.8 °C at 760 mmHg |
| Flash Point: | 71.1 °C |
| Solubility: | slightly soluble in water |
| Appearance: | yellow liquid with an odour of cinnamon |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38-43 |
| Safety: | 26-36/37 |
| PSA: | 17.07000 |
| LogP: | 1.89870 |
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| Conditions | Yield |
|---|---|
| With dimethyl selenoxide In dichloromethane for 7h; Heating; | 100% |
| With 2,2'-bipyridylchromium peroxide In benzene for 1.25h; Heating; | 100% |
| With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 63h; Heating; | 100% |
- 26958-41-8
cinnamyl-1,3-dithiane
- 104-55-2
3-phenyl-propenal
| Conditions | Yield |
|---|---|
| With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 1h; micellar medium; | 100% |
| With dimethyl sulfoxide at 20℃; for 1h; Reagent/catalyst; Solvent; | 94% |
| With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 1h; Micellar solution; | 92% |
| Conditions | Yield |
|---|---|
| With water at 20℃; for 2h; | 100% |
| With boron trifluoride diethyl etherate; tetraethylammonium iodide In chloroform for 2h; Heating; | 81% |
| With sulfuric acid In nitromethane for 48h; Ambient temperature; Yield given; |
- 83977-12-2, 5660-60-6
2-((E)-Styryl)-[1,3]dioxolane
- 104-55-2
3-phenyl-propenal
| Conditions | Yield |
|---|---|
| With water at 20℃; for 2h; | 100% |
| With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 1h; Heating; | 97% |
| With tetrachlorosilane In dichloromethane at 20℃; for 0.25h; | 96% |
| Conditions | Yield |
|---|---|
| With iodosylbenzene; 4 A molecular sieve; sodium ruthenate(VI) In dichloromethane at 20℃; for 3h; Oxidation; | 100% |
| With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1-ethyl-3-methylimidazolium hexafluorophosphate In dichloromethane at 20℃; for 1h; | 95% |
| With N-Bromosuccinimide; β‐cyclodextrin In methanol; water; acetone at 20℃; for 8h; | 94% |
| Conditions | Yield |
|---|---|
| With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 1h; | 100% |
| With bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen; toluene-4-sulfonic acid; 1,3,5-trimethyl-benzene In tert-butyl alcohol at 25℃; under 760.051 Torr; for 7h; | 94% |
| With manganese(IV) oxide; benzyl-methyl-amine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Solvent; | 78% |
| Conditions | Yield |
|---|---|
| With water at 20℃; for 2h; | 100% |
| With iron(III) p-toluenesulfonate hexahydrate In water at 20℃; for 4h; | 96% |
- 61912-03-6
2-hydroxy-4-phenyl-3-butenenitrile
- 104-55-2
3-phenyl-propenal
| Conditions | Yield |
|---|---|
| With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 100% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry; | 99.9% |
| With formic acid; platinum(IV) oxide In water at 55 - 60℃; for 20h; | 56% |
- 37973-54-9, 64847-78-5
1,1-diacetoxy-3-phenylprop-2-ene
- 104-55-2
3-phenyl-propenal
| Conditions | Yield |
|---|---|
| With tin(ll) chloride In acetonitrile at 25℃; for 0.0333333h; Hydrolysis; | 99% |
| With pyrographite In dichloromethane for 0.25h; Heating; | 98% |
| With iron(II) sulfate In dichloromethane for 0.25h; Heating; | 98% |
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History
Cinnamaldehyde (CAS NO.104-55-2) was isolated from cinnamon essential oil in 1834 by Dumas and Péligot and synthesized in the laboratory by Chiozza in 1856.
Specification
1. Introduction of Cinnamaldehyde
Cinnamaldehyde is the organic compound that gives cinnamon its flavor and odor. This pale yellow, viscous liquid occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum. The IUPAC Name of it is (E)-3-phenylprop-2-enal.
2. Properties of Cinnamaldehyde
Index of Refraction: 1.577
Molar Refractivity: 42.32 cm3
Molar Volume: 127.7 cm3
Polarizability: 16.78×10-24cm3
Surface Tension: 38.9 dyne/cm
Density: 1.034 g/cm3
Flash Point: 71.1 °C
Enthalpy of Vaporization: 48.4 kJ/mol
Melting Point: −9-−4 °C(lit.)
Boiling Point: 246.8 °C at 760 mmHg
Vapour Pressure: 0.0265 mmHg at 25°C
Water Solubility: Slightly soluble
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
Physical Appearance: yellow liquid with an odour of cinnamon
Product Categories: Pharmaceutical Intermediates;Aromatic Aldehydes & Derivatives (substituted);Alphabetical Listings;C-DFlavors and Fragrances;Certified Natural Products;Flavors and Fragrances
3. Structure Descriptors of Cinnamaldehyde
The molecule of cinnamaldehyde consists of a phenyl group attached to an unsaturated aldehyde. As such, the molecule can be viewed as a derivative of acrolein. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.
4. Toxicity of Cinnamaldehyde
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | oral | 1160mg/kg (1160mg/kg) | BEHAVIORAL: COMA | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
| mouse | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 16, 1967. | |
| mouse | LD50 | intravenous | 75mg/kg (75mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07571, | |
| mouse | LD50 | oral | 2225mg/kg (2225mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Yakugaku Zasshi. Journal of Pharmacy. Vol. 92, Pg. 135, 1972. |
| mouse | LDLo | parenteral | 200mg/kg (200mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 687, 1955. | |
| rat | LD50 | oral | 2220mg/kg (2220mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
5. Safety Information of Cinnamaldehyde
Hazard Codes: 
Xi
Risk Statements: 36/37/38-43
R36/37/38:Irritating to eyes, respiratory system and skin.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: GD6476000
F: 10-23
HS Code: 29122900
6. Preparation of Cinnamaldehyde
Although Cinnamaldehyde is obtained from Chinese cassia oils, it is synthesized by action of alkali upon a mixture of benzaldehyde and acetaldehyde.
C6H5CH=O + CH3CH=O → C6H5CH=CHCH=O
This and most other products for fragrances must be purified by, for example, vacuum fractionation.
7. Use of Cinnamaldehyde
1) The extensive use for Cinnamaldehyde is as a flavoring.Concentrations required for flavoring food items like chewing gum, candy, ice cream,and beverages range from 9 to 4900 ppm (that is, less than 0.5%).
2) Cinnamaldehyde is used in some perfumes of natural, sweet, or fruity scents. Almond, apricot, butterscotch, and other aromas may partially employ the compound for their pleasant smells.
3) Cinnamaldehyde can be used as a food adulterant; powdered beechnut husk aromatized with cinnamaldehyde can be marketed as powdered cinnamon.
4) Cinnamaldehyde is also used as a fungicide. .
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