Allocinnamic acid

Chemical compound From Wikipedia, the free encyclopedia

Allocinnamic acid is a cis-isomer of cinnamic acid, into which the cinnamic acid is easily converted.[1][2]

Quick facts Names, Identifiers ...
Allocinnamic acid
Names
IUPAC name
(Z)-3-phenylprop-2-enoic acid
Other names
cis-β-carboxystyrene, cis-cinnamic acid;
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.262.470 Edit this at Wikidata
EC Number
  • 827-073-9
279588
UNII
  • InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-
    Key: WBYWAXJHAXSJNI-SREVYHEPSA-N
  • C1=CC=C(C=C1)C=CC(=O)O
Properties
C9H8O6
Molar mass 212.157 g·mol−1
Appearance colorless crystals
Density 1.49 g/cm³
Melting point 68 °C (154 °F; 341 K)
Boiling point 265 °C (509 °F; 538 K)
soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Allocinnamic acid was first discovered by Carl Liebermann in 1890 in coca leaves,[3][4] then Liebermann found that this acid is formed during the reduction (by zinc dust in an alcoholic solution during boiling) of β-dibromopropiolic acid.

Physical properties

Allocinnamic acid crystallizes in the form of three crystalline modifications with melting points of 68 °C, 58 °C, and 42 °C.[5][6] It is hardly soluble in water and cold ligroin, easily soluble in alcohol and ether, and does not change in dim light.[7]

Chemical properties

When heated briefly with concentrated sulfuric acid, the compound turns into cinnamic acid.[3]

It forms liquid anhydride with acetic anhydride, which turns into cinnamic acid anhydride when heated.

References

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