Cinnamic acid

Base Information

• Chemical Name: Cinnamic acid
• CAS No.: 140-10-3
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 29163900
• European Community (EC) Number: 210-708-3
• NSC Number: 623441,44010,9189
• UNII: U14A832J8D
• DSSTox Substance ID: DTXSID5022489
• Nikkaji Number: J2.024I,J2.087G
• Wikipedia: Cinnamic acid
• Wikidata: Q164785
• RXCUI: 2621720
• Pharos Ligand ID: SDWA6YB1C7G2
• Metabolomics Workbench ID: 37506
• ChEMBL ID: CHEMBL27246
• Mol file: 140-10-3.mol

Synonyms:(E)-cinnamic acid, 2-(14)C-labeled cpd;cinnamic acid;cinnamic acid, (trans)-(E)-isomer;cinnamic acid, (Z)-isomer;cinnamic acid, 1-(13)C-labeled cpd;cinnamic acid, 1-14C-labeled cpd;cinnamic acid, 13C-labeled cpd;cinnamic acid, 14C-labeled cpd;cinnamic acid, 14C-labeled cpd (E)-isomer;cinnamic acid, 2-(13)C-labeled cpd;cinnamic acid, 2-(14)C-labeled cpd;cinnamic acid, 3-(14)C-labeled cpd;cinnamic acid, 3H-labeled cpd (E)-isomer;cinnamic acid, 3H-labeled cpd (Z)-isomer;cinnamic acid, ion(1-);cinnamic acid, ion(1-)-(E)-isomer;cinnamic acid, nickel (+2) salt;cinnamic acid, potassium salt;cinnamic acid, radical ion(1-);cinnamic acid, sodium salt;cinnamic acid, sodium salt(E)-isomer;cinnamic acid, sodium salt(Z)-isomer;cinnamic acid, zinc salt(E)-isomer;cis-cinnamic acid;E-cinnamic acid;E-Z cinnamic acid;sodium cinnamate;trans-cinnamic acid;tritium labeled (E)-cinnamic acid;tritium labeled (Z)-cinnamic acid

Chemical Property of Cinnamic acid

Chemical Property:

• Appearance/Colour: White to almost white crystalline powder
• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 133 °C(lit.)
• Refractive Index: 1.616
• Boiling Point: 265 °C at 760 mmHg
• PKA: 4.44(at 25℃)
• Flash Point: 189.5 °C
• PSA: 37.30000
• Density: 1.184 g/cm³
• LogP: 1.78440
• Storage Temp.: Store at RT.
• Solubility.: 0.4g/l
• Water Solubility.: 0.4 g/L (20 ºC)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

≥ 99% ^*data from raw suppliers

Cinnamic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(=O)O
• Uses: trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber. trans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.

Technology Process of Cinnamic acid

There total 651 articles about Cinnamic acid 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: 85.0%

cyclohexanepropionic acid (701-97-3) → (E)-3-phenylacrylic acid (140-10-3) + (E)-3-cyclohexylprop-2-enoic acid (56453-86-2)

Guidance literature:

cyclohexanepropionic acid; With Zn(2,2,6,6-tetramethylpiperidine)_2*2LiCl; zinc(II) chloride; In tetrahydrofuran; at -40 ℃; for 1.5h; Inert atmosphere; Sealed tube;

With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate; In tetrahydrofuran; at -40 - 60 ℃; for 12h; diastereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201706893

Reference yield: 42.5%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + carbon dioxide (124-38-9,18923-20-1) → hydratropic acid (492-37-5,2328-24-7) + (E)-3-phenylacrylic acid (140-10-3) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; at -78 - 85 ℃;

DOI:10.1016/0022-328X(86)80487-9

Reference yield: 11.0%

trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5) → (E)-3-phenylacrylic acid (140-10-3) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7)

Guidance literature:

With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; iodosylbenzene; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1039/P19960002309

upstream raw materials:

pyridine

malonic acid

(diethoxymethyl)benzene

benzaldehyde

Downstream raw materials:

(+/-)-5-hydroxy-7-methyl-4-phenyl-3,4-dihydrocoumarin

3,4-Dihydro-7-hydroxy-5-methyl-4-phenylcoumarin

(E)-propyl cinnamate

ethyl 3-phenylheptanoate

Refernces

• 1、 Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.. "A Rapid and Efficient Microwave-Assisted Synthesis of Substituted 3-Phenylpropionic Acids from Benzaldehydes in Minutes". . p. 1186 - 1187. Retrieved 2003.
• 2、 Saito, Shinichi,Nakagawa, Satomi,Koizumi, Toru,Hirayama, Kyoko,Yamamoto, Yoshinori. "Nickel-mediated regio- and chemoselective carboxylation of alkynes in the presence of carbon dioxide". . p. 3975 - 3978. Retrieved 1999.
• 3、 Ali, Liaqat,Rizvi, Tania Shamim,Ahmad, Manzoor,Shaheen, Farzana. "New iridoid glycoside from Gratiola officinalis". . p. 1191 - 1195. Retrieved 2012.
• 4、 Takemoto,Yasuda,Ley. "Solid-supported reagents for the oxidation of aldehydes to carboxylic acids". . p. 1555 - 1556. Retrieved 2001.
• 5、 Utermohlen,Wallace. "-". . p. 547. Retrieved 1947.
• 6、 Wade et al.. "". . p. 731. Retrieved 1978.
• 7、 Obermayer, David,Damm, Markus,Kappe, C. Oliver. "Simulating microwave chemistry in a resistance-heated autoclave made of semiconducting silicon carbide ceramic". . p. 15827 - 15830. Retrieved 2013.
• 8、 Erlenmeyer,Gaertner. "". . p. 145,146, 148. Retrieved 1936.
• 9、 Koppel,Kinnick. "Carboxyvinylation; a one step synthesis of α,β unsaturated acids". . p. 711 - 713. Retrieved 1974.
• 10、 Kistiakowsky,Smith. "-". . p. 2428. Retrieved 1936.