Chemistry:Allocinnamic acid
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| Names | |
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| IUPAC name
(Z)-3-phenylprop-2-enoic acid
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| Other names
cis-β-carboxystyrene, cis-cinnamic acid;
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| EC Number |
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| 279588 | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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). | |
| 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" (in en). NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C102943.
- ↑ 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.
- ↑ 3.0 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.
- ↑ 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.
- ↑ 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.
- ↑ (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.
- ↑ 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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