Allocinnamic acid

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Allocinnamic acid
Allokorichnaia kislota.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 827-073-9
279588
PubChem CID
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
Appearancecolorless 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).

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

Contents

Synthesis

Allocinnamic acid was first discovered by Сarl 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

  1. ↑ Informatics, NIST Office of Data and. "(Z)-3-Phenyl-2-propenoic acid". NIST . Retrieved 13 June 2025.
  2. ↑ Senning, Alexander (30 October 2006). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. p. 14. ISBN   978-0-08-048881-3 . Retrieved 13 June 2025.
  3. 1 2 Quarterly Journal of the Chemical Society of London. Chemical Society (Great Britain). 1890. p. 1417. Retrieved 13 June 2025.
  4. ↑ Gattermann, Ludwig (1896). The Practical Methods of Organic Chemistry. Macmillan. p. 268. Retrieved 13 June 2025.
  5. ↑ Whitmore, Frank C. (14 December 2011). Organic Chemistry, Volume Two: Part III: Aromatic Compounds Part IV: Heterocyclic Compounds Part V: Organophosphorus and Organometallic Compounds. Courier Dover Publications. p. 703. ISBN   978-0-486-60701-6 . Retrieved 13 June 2025.
  6. ↑ Ullmann's Fine Chemicals. John Wiley & Sons. 7 January 2014. ISBN   978-3-527-68359-8 . Retrieved 13 June 2025.
  7. ↑ Lee, Ho-Hi; Senda, Hitoshi; Kuwae, Akio; Hanai, Kazuhiko (1 May 1994). "Crystal and Molecular Structures of Allocinnamic Acid" . Bulletin of the Chemical Society of Japan . 67 (5): 1475–1478. doi:10.1246/bcsj.67.1475 . Retrieved 13 June 2025.
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