Allocinnamic acid

Allocinnamic acid
Names
	IUPAC name (Z)-3-phenylprop-2-enoic acid
	Other names cis-β-carboxystyrene, cis-cinnamic acid;
Identifiers
CAS Number	102-94-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35699;
ChemSpider	10286933;
ECHA InfoCard	100.262.470
EC Number	827-073-9;
Gmelin Reference	279588
PubChem CID	5372954;
UNII	YB7ZGY8NE2;
CompTox Dashboard (EPA)	DTXSID001019000;
	InChI 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;
	SMILES C1=CC=C(C=C1)C=CC(=O)O;
Properties
Chemical formula	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)
Solubility in water	soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

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

^ Informatics, NIST Office of Data and. "(Z)-3-Phenyl-2-propenoic acid". NIST. Retrieved 13 June 2025.
^ 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.
^ ^a ^b Quarterly Journal of the Chemical Society of London. Chemical Society (Great Britain). 1890. p. 1417. Retrieved 13 June 2025.
^ Gattermann, Ludwig (1896). The Practical Methods of Organic Chemistry. Macmillan. p. 268. Retrieved 13 June 2025.
^ 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.
^ Ullmann's Fine Chemicals. John Wiley & Sons. 7 January 2014. ISBN 978-3-527-68359-8. Retrieved 13 June 2025.
^ 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.

[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.

[QJ-3] 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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