Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID InChI1 InChIKey1 SMILES1. |
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey. |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| ChemSpiderID = 610577 |
| ChemSpiderID = 610577 |
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| InChI = 1/C15H12O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H,(H,16,17)/b14-11+ |
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| InChIKey = BIDDLDNGQCUOJQ-SDNWHVSQBV |
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| SMILES1 = O=C(O)\C(=C\c1ccccc1)c2ccccc2 |
| SMILES1 = O=C(O)\C(=C\c1ccccc1)c2ccccc2 |
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| StdInChI = 1S/C15H12O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H,(H,16,17)/b14-11+ |
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| StdInChIKey = BIDDLDNGQCUOJQ-SDNWHVSQSA-N |
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| CASNo = 91-48-5 |
| CASNo = 91-48-5 |
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| SMILES = OC(=O)C(=C/C1=CC=CC=C1)/C2=CC=CC=C2}} |
| SMILES = OC(=O)C(=C/C1=CC=CC=C1)/C2=CC=CC=C2}} |
Revision as of 11:03, 29 November 2010
Names | |
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IUPAC name
(2E)-2,3-Diphenylprop-2-enoic acid
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Other names
α-Phenylcinnamic acid, α-(Phenylmethylene)benzeneacetic acid, α-Phenyl-trans-cinnamic acid
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.882 |
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Properties | |
C15H12O2 | |
Molar mass | 224.259 g·mol−1 |
Appearance | White to light yellow powder |
Melting point | 172-174 °C |
Boiling point | 224-225 °C |
Slightly soluble | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Irritant[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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α-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C15H12O2 and appears as an off-white crystalline solid[2].
Uses
α-Phenylcinnamic acid is frequently used as a compound synthesized in undergraduate laboratories to study the Perkin reaction, but is primarily seen as in intermediate or precursor to other, more useful phenylpropanoids.
Synthesis
There are many ways to synthesize α-phenylcinnamic acid. Some of the more popular methods of formation include the condensation of phenylacetyl chloride with benzaldehyde in the presence of triethylamine, the distillation of benzylmandelic acid, or by the reaction of sodium phenylacetate with benzaldehyde in acetic anhydride [3]. There are two isomers of this compound, differing in the geometry of the alkene. The E isomer, in which the two phenyl rings are cis to each other, is the major product formed by most synthetic routes. However, this compound can be converted using heat or ultraviolet light into a mixture containing nearly 50% of the Z isomer.[4]
References
- ^ http://msds.chem.ox.ac.uk/PH/alpha-phenyl_cinnamic_acid.html
- ^ http://www.chemexper.com/search/cas/91485.html
- ^ Organic Syntheses, Coll. Vol. 4, p.777 (1963); Vol. 33, p.70 (1953).Link
- ^ István Pálinkó, Béla Török, Gyula Tasi, Tamás Körtvélyesi. "Experimental and Computational Tools for Mechanistic Study: A Modified Perkin Condensation leading to Alpha-Phenylcinnamic Acid Isomers". Electronic Conferences on Trends in Organic Chemistry: ECTOC-1: June 12-July 7, 1995.
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: CS1 maint: multiple names: authors list (link)