cis-Cinnamic acid

Base Information

• Chemical Name: cis-Cinnamic acid
• CAS No.: 102-94-3
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.161
• European Community (EC) Number: 827-073-9
• NSC Number: 174025
• UNII: YB7ZGY8NE2
• DSSTox Substance ID: DTXSID001019000
• Nikkaji Number: J1.966F
• Wikidata: Q4062664
• Metabolomics Workbench ID: 37312
• Mol file: 102-94-3.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 cis-Cinnamic acid

Chemical Property:

• Melting Point: 42°C
• Refractive Index: 1.5049 (estimate)
• Boiling Point: 264.999 °C at 760 mmHg
• PKA: 4.34±0.10(Predicted)
• Flash Point: 189.53 °C
• PSA: 37.30000
• Density: 1.185 g/cm³
• LogP: 1.78440
• Water Solubility.: 8.45g/L(25 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

(Z)-3-PHENYL-2-PROPENOIC ACID 95.00% ^*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)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\C(=O)O

Technology Process of cis-Cinnamic acid

There total 101 articles about cis-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: 95.0%

diisopropylammonium (Z)-3-phenylacrylate (1265912-86-4) → cis-cinnamic acid (140-10-3,621-82-9,102-94-3)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1021/jm1011676

Reference yield: 79.0%

(E)-3-phenylacrylic acid (140-10-3) → cis-cinnamic acid (140-10-3,621-82-9,102-94-3)

Guidance literature:

With triethanolamine; C₃₃H₂₁IrN₃O₉S₃^(3-); Alkaline conditions; Irradiation;

DOI:10.1039/c9sc04584h

Reference yield: 78.0%

carbon dioxide (124-38-9,18923-20-1) + (Z)-β-bromostyrene (588-73-8,1340-14-3) → cis-cinnamic acid (140-10-3,621-82-9,102-94-3)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; dichloro(2,2'-bipyridine)nickel(II); In N,N-dimethyl-formamide; at -10 ℃; under 760 Torr; Electrolysis;

DOI:10.1246/cl.2005.528

upstream raw materials:

hydratropic acid

(E)-3-phenylacrylic acid

2-benzylidenemalonic acid

truxillic acid

Downstream raw materials:

methyl (2Z)-3-phenylprop-2-enoate

N-benzoyl-O-cis-cinnamoyl-hydroxylamine

3-(2,4-dimethyl-phenyl)-3-phenyl-propionic acid

(E)-3-phenylacrylic acid

Refernces

• 1、 Fuchs,Bloomfield. "". . p. 3423. Retrieved 1966.
• 2、 Cattò, Cristina,Dell'Orto, Silvia,Villa, Federica,Villa, Stefania,Gelain, Arianna,Vitali, Alberto,Marzano, Valeria,Baroni, Sara,Forlani, Fabio,Cappitelli, Francesca. "Unravelling the structural and molecular basis responsible for the anti-biofilm activity of zosteric acid". . . Retrieved 2015.
• 3、 Mizuno, Takahiro,Murai, Toshiaki,Shibahara, Fumitoshi,Shibata, Yoshifuru. "Transfer semihydrogenation of alkynes catalyzed by imidazo[1,5-a]pyrid-3-ylidenepd complexes: Positive effects of electronic and steric features on N-heterocyclic carbene ligands". . p. 332 - 337. Retrieved 2020.
• 4、 Sandris. "". . p. 3583. Retrieved 1968.
• 5、 Bellasoued, Moncef,Gaudemar, Marcel. "STEREOSELECTIVE SYNTHESIS OF (E)-α,β-UNSATURATED ACIDS FROM C,O,O-TRI(TRIMETHYLSILYL) KETENE ACETAL AND ALDEHYDS". . p. 4551 - 4554. Retrieved 1988.
• 6、 Strel'zowa,Schilow. "-". . . Retrieved 1957.
• 7、 Nikolc,Uscumlic,Juranic. "A linear solvation energy relationship study for the reactivity of 2-(4-substituted phenyl)-cyclohe-1-enecarboxylic, 2-(4-substituted phenyl)-benzoic, and 2-(4-substituted phenyl)-acrylic acids with diazodiphenylmethane in various solvents". . p. 430 - 439. Retrieved 2010.
• 8、 Kerzig, Christoph,Wenger, Oliver S.. "Reactivity control of a photocatalytic system by changing the light intensity". . p. 11023 - 11029. Retrieved 2019.
• 9、 Homsi, Fadi,Rousseau, Gerard. "Halodecarboxylation of α,β-acetylenic and α,β-ethylenic acids". . p. 1495 - 1498. Retrieved 1999.
• 10、 Ribas,Vidal. "". . p. 252. Retrieved 1966.