cis-Cinnamaldehyde

Base Information

• Chemical Name: cis-Cinnamaldehyde
• CAS No.: 57194-69-1
• Molecular Formula: C9H8 O
• Molecular Weight: 132.162
• UNII: W3HD274KF5
• DSSTox Substance ID: DTXSID101020957
• Nikkaji Number: J918.664F
• Wikidata: Q27161918
• Metabolomics Workbench ID: 45250
• ChEMBL ID: CHEMBL2289233
• Mol file: 57194-69-1.mol

Synonyms:cis-Cinnamaldehyde;(Z)-cinnamaldehyde;57194-69-1;(Z)-3-phenylprop-2-enal;(2Z)-3-phenylprop-2-enal;cis-Cinnamic aldehyde;(z)-3-phenylacrylaldehyde;(Z)-3-Phenyl-2-propenal;2-Propenal, 3-phenyl-, (2Z)-;(Z)-Cinnamylaldehyde;Cinnamaldehyde, (Z)-;2-Propenal, 3-phenyl-, (Z)-;W3HD274KF5;CHEBI:89729;cis-3-phenyl-propenal;(2Z)-3-phenylacrylaldehyde;UNII-W3HD274KF5;3-Phenyl-(Z)-2-Propenal;(2Z)-3-phenyl-2-propenal;(Z)-3-PHENYLPROPENAL;SCHEMBL159856;CHEMBL2289233;CIS-3-PHENYL-2-PROPENAL;DTXSID101020957;AKOS015962539;EN300-7301892;Q27161918;9Y3

Chemical Property of cis-Cinnamaldehyde

Chemical Property:

• Boiling Point: 246.8°Cat760mmHg
• Flash Point: 71.1°C
• PSA: 17.07000
• Density: 1.034g/cm³
• LogP: 1.89870
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• 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% ^*data from raw suppliers

cis-Cinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC=O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\C=O
• Uses: cis-Cinnamaldehyde acts as an antibacterial agent against Escherichia Coli and Salmonella in vitro. Causes cell structural damage resulting in leakage of cellular content. cis-Cinnamaldehyde is derived from (Z)-Cinnamyl Alcohol (C442105), a useful synthetic intermediate and is also used as a reagent in the synthesis of one-dimensional ZnO nanorods with well-defined morphology as highly selective photocatalyst.

Technology Process of cis-Cinnamaldehyde

There total 28 articles about cis-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: 92.0%

(Z)-cinnamyl alcohol (4510-34-3) → cinnamaldehyde (57194-69-1)

Guidance literature:

With C₃₀H₂₄N₂O₇W; dihydrogen peroxide; In water; acetonitrile; for 14h; Reflux;

DOI:10.1002/ejic.200701043

Reference yield: 63.0%

3-Phenyl-2-propyn-1-ol (1504-58-1) → (E)-3-phenylpropenal (14371-10-9) + cinnamaldehyde (57194-69-1)

Guidance literature:

tris(triphenylphosphine)ruthenium(II) chloride; tributylphosphine; In toluene; for 48h; Heating;

DOI:10.1039/c39890000890

Reference yield: 62.0%

3-Phenylpropenol (104-54-1) → (E)-3-phenylpropenal (14371-10-9) + cinnamaldehyde (57194-69-1)

Guidance literature:

With manganese(IV) oxide; In hexane; at 20 ℃; for 20h;

DOI:10.1039/c4cc00310a

upstream raw materials:

Phenylpropargyl aldehyde

phenylpropargyl aldehyde diethyl acetal

(2Z)-2-bromo-3-phenyl-2-propenal

formic acid

Downstream raw materials:

(2E,4E)-2-cyano-5-phenyl-2,4-pentadienoic acid methyl ester

Refernces

• 1、 Ogumi, Zempachi,Mizoe, Toshiyuki,Zhen, Chen,Takehara, Zen-ichiro. "Application of the SPE Method to Organic Electrochemistry-X. Behaviors of the Manganese Redox Couple Incorporated in Pt-Nafion and Their Mediatory Oxidation of Cinnamyl Alcohol to Cinnamaldehyd". . p. 3365 - 3368. Retrieved 1990.
• 2、 Wu, Qiuyue,Dong, Ziyang,Xu, Jiaxi,Yang, Zhanhui. "Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights". supporting information. p. 3173 - 3180. Retrieved 2021/04/21.
• 3、 Saito, Hiroki,Kato, Ranmaru,Ikeuchi, Kazutada,Suzuki, Takahiro,Tanino, Keiji. "8π Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes". supporting information. p. 9606 - 9610. Retrieved 2021/12/17.