Cinnamaldehyde

Base Information

• Chemical Name: Cinnamaldehyde
• CAS No.: 14371-10-9
• Molecular Formula: C9H8O
• Molecular Weight: 132.162
• Hs Code.: 29122990
• European Community (EC) Number: 203-213-9,604-377-8,946-230-3
• NSC Number: 40346,16935
• UNII: SR60A3XG0F
• DSSTox Substance ID: DTXSID6024834
• Nikkaji Number: J2.850I,J43.393D
• Wikipedia: Cinnamaldehyde
• Wikidata: Q204036
• NCI Thesaurus Code: C76703
• RXCUI: 1368153
• Pharos Ligand ID: JFB6JYGKLS9F
• Metabolomics Workbench ID: 38332
• ChEMBL ID: CHEMBL293492
• Mol file: 14371-10-9.mol

Synonyms:3-phenyl-2-propenal;3-phenylprop-2-enaldehyde;beta-phenylacrolein;cinnamaldehyde;cinnamic aldehyde;cinnamic aldehyde, (E)-isomer;supercinnamaldehyde;trans-3-phenylprop-2-enaldehyde;trans-cinnamaldehyde

Chemical Property of Cinnamaldehyde

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 0.0265mmHg at 25°C
• Melting Point: -9--4 °C(lit.)
• Refractive Index: n20/D 1.622(lit.)
• Boiling Point: 246.841 °C at 760 mmHg
• Flash Point: 71.111 °C
• PSA: 17.07000
• Density: 1.035 g/cm³
• LogP: 1.89870
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• Water Solubility.: 1.1 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 132.057514874
• Heavy Atom Count: 10
• Complexity: 121

Purity/Quality:

99.9% ^*data from raw suppliers

trans-Cinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-21
• Safety Statements: 26-36/37-37/39-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C1=CC=C(C=C1)C=CC=O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C=O
• Recent ClinicalTrials: Desensitization of Nociceptive Afferents by Application of Topical Capsaicin, Trans-cinnamaldehyde and L-menthol
• Uses: trans-Cinnamaldehyde is used in the flavor and perfume industry. It is also used in medicine. It reacts with glutathione to get an adduct 1'-(glutathion-S-yl)-dihydrocinnamaldehyde. It is used to prepare cinnamylidene-bisacetamide by reacting with acetamide. Further, it inhibits xanthine oxidase. Buildingblock - Cinnamaldehyde is an unsaturated aldehyde so it can easily react to many different compounds to be used in a wide range of fragrance compositions. It is also a building block for several agrochemicals (miticides) or for derivatives like cinnamic alcohol, 3-phenylpropanol, cinnamonitrile, 3-phenylpropionylaldehyde (fragrances and as an alternative to enalapril, lisinopril and ramipril).

Technology Process of Cinnamaldehyde

There total 468 articles about Cinnamaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) + benzyl alcohol (100-51-6,185532-71-2) → (E)-3-phenylpropenal (14371-10-9) + benzaldehyde (100-52-7)

Guidance literature:

With potassium carbonate; In toluene; at 20 ℃; for 12h;

DOI:10.1002/adsc.201000591

Reference yield: 82.0%

trans,trans-1,4-Diphenyl-1,3-butadiene (886-65-7,538-81-8) → (E)-3-phenylpropenal (14371-10-9) + benzaldehyde (100-52-7)

Guidance literature:

With iron(III) sulfate hydrate; oxygen; In water; acetonitrile; at 45 ℃; for 24h; regioselective reaction;

DOI:10.1021/acs.orglett.9b03562

Reference yield: 72.0%

1-propenylbenzene (873-66-5) → (E)-3-phenylpropenal (14371-10-9) + benzaldehyde (100-52-7)

Guidance literature:

With 2-iodo-5-nitrothiophene; In acetonitrile; for 0.75h; Irradiation;

upstream raw materials:

maleic anhydride

N-phenylcinnamaldimine

styrene

3-(N-Methylanilino)-2-propenal

Downstream raw materials:

2-[(E,E)-4-phenylbuta-1,3-dienyl]pyridine

2-benzyl-5-phenyl-penta-2,4-dienal

5-oxo-3,4,5-triphenyl-valeraldehyde

4-trans-cinnamylidene-2-phenyl-4H-oxazol-5-one

Refernces

• 1、 Yamaguchi, Jun-ichi,Yamamoto, Shiori,Takeda, Takeshi. "CuBr2-LiOBut as a New Reagent for Oxidation of Alcohols". . p. 1185 - 1188. Retrieved 1992.
• 2、 Andrews. "-". . p. 3062,3065. Retrieved 1947.
• 3、 Fielder,Rowan. "The synthesis of 6,6,6-2H3-2E-hexenal". . p. 199 - 204. Retrieved 1994.
• 4、 Liao, Yihua,Shabany, Hossein,Spilling, Christopher D.. "The preparation of acyl phosphonates by the heterogeneous oxidation of 1-hydroxy phosphonates". . p. 8389 - 8392. Retrieved 1998.
• 5、 Sahu, Debojeet,Sarmah, Chandan,Das, Pankaj. "A highly efficient and recyclable silica-supported palladium catalyst for alcohol oxidation reaction". . p. 3422 - 3425. Retrieved 2014.
• 6、 Itoh, Akichika,Kodama, Tomohiro,Masaki, Yukio. "New synthetic method of benzaldehydes and α,β-unsaturated aldehydes with I2 under photoirradiation". . p. 686 - 687. Retrieved 2001.
• 7、 Nunno, L. Di.,Scilimati, A.. "SELECTIVE REDUCTION OF ALDEHYDES TO THE CORRESPONDING PRIMARY ALCOHOLS BY LITHIUM ENOLATE OF ACETALDEHYDE". . p. 3639 - 3644. Retrieved 1988.
• 8、 Gangloff, Anthony R.,Judge, Thomas M.,Helquist, Paul. "Light-Induced, Iodine-Catalyzed Aerobic Oxidation of Unsaturated Tertiary Amines". . p. 3679 - 3682. Retrieved 1990.
• 9、 Goettmann, Frederic,Le Floch, Pascal,Sanchez, Clement. "Highly regioselective terminal alkynes hydroformylation and Pauson-Khand reaction catalysed by mesoporous organised zirconium oxide based powders". . p. 180 - 182. Retrieved 2006.
• 10、 Luan, Yi,Wang, Ge,Luck, Rudy L.,Yang, Mu,Han, Xiao. "Oxidation of alcohols with hydrogen peroxide catalyzed by molybdenum(VI)-peroxo complex under solvent-free conditions". . p. 1236 - 1237. Retrieved 2007.