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 | |
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| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| 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).
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Allocinnamic acid is a cis-isomer of cinnamic acid, into which the cinnamic acid is easily converted.[1][2]
Synthesis
[edit | edit source]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
[edit | edit source]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
[edit | edit source]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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