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 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:35699

ChemSpider |

* 10286933

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

Tracking categories (test):

* SizeSet

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

## Contents

* 1 Synthesis
* 2 Physical properties
* 3 Chemical properties
* 4 References

## 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" (in en). NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C102943.
2. ↑ Senning, Alexander (30 October 2006) (in en). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. p. 14. ISBN 978-0-08-048881-3. https://books.google.com/books?id=Fl4sdCYrq3cC&dq=Allocinnamic+acid&pg=PA14. Retrieved 13 June 2025.
3. ↑ 3.0 3.1 (in en) Quarterly Journal of the Chemical Society of London. Chemical Society (Great Britain). 1890. p. 1417. https://books.google.com/books?id=rALzAAAAMAAJ&dq=Allocinnamic+acid++sulfuric+acid,&pg=PA1417. Retrieved 13 June 2025.
4. ↑ Gattermann, Ludwig (1896) (in en). The Practical Methods of Organic Chemistry. Macmillan. p. 268. https://books.google.com/books?id=IR2-Lhipf30C&dq=Allocinnamic+acid&pg=PA268. Retrieved 13 June 2025.
5. ↑ Whitmore, Frank C. (14 December 2011) (in en). 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. https://books.google.com/books?id=jgZLDwAAQBAJ&dq=Allocinnamic+acid++sulfuric+acid,&pg=PA703. Retrieved 13 June 2025.
6. ↑ (in en) Ullmann's Fine Chemicals. John Wiley & Sons. 7 January 2014. ISBN 978-3-527-68359-8. https://books.google.com/books?id=yZqOAgAAQBAJ&dq=Allocinnamic+acid&pg=PA427. 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. https://academic.oup.com/bcsj/article-abstract/67/5/1475/7349270?redirectedFrom=fulltext. Retrieved 13 June 2025.

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*[CID]: Compound ID
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