Tropic acid

Tropic acid
Names
Preferred IUPAC name
3-Hydroxy-2-phenylpropanoic acid
Other names
2-Phenylhydracrylic acid; Tropate
Identifiers
CAS Number
  • 529-64-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:CHEBI:30765 checkY
ChemSpider
  • 10274 checkY
ECHA InfoCard 100.008.201 Edit this at Wikidata
EC Number
  • 209-020-6
KEGG
  • C01456 checkY
MeSH C011377
PubChem CID
  • 10726
UNII
  • 9RM4U80765 checkY
CompTox Dashboard (EPA)
  • DTXSID90862179 Edit this at Wikidata
InChI
  • InChI=1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12) checkY
    Key: JACRWUWPXAESPB-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
    Key: JACRWUWPXAESPB-UHFFFAOYAV
  • C1=CC=C(C=C1)C(CO)C(=O)O
Properties
Chemical formula
 C9H10O3
Molar mass 166.176 g·mol−1
Melting point 116 °C (241 °F; 389 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Tropic acid is a chemical with IUPAC name 3-hydroxy-2-phenylpropanoic acid and condensed structural formula HOCH2CHPhCOOH. It is a laboratory reagent used in the chemical synthesis of atropine and hyoscyamine. Tropic acid is a chiral substance, existing as either a racemic mixture or as a single enantiomer.

Synthesis

Tropic acid can be prepared by the Ivanov reaction between phenylacetic acid and formaldehyde. In this method, the dianion of the acid is formed using a Grignard reagent, isopropyl magnesium chloride, and this reacts with the aldehyde to form the magnesium salt of the product, from which the pure acid is obtained after acidification with sulfuric acid.[1]

Many other methods have been used to make tropic acid, for example starting from acetophenone (1).[2]

Uses

Tropic acid is used in the chemical synthesis of atropine and hyoscyamine.[1]

References

  1. ^ a b Blicke, F. F.; Raffelson, Harold; Barna, Bohdan (1952). "The Preparation of Tropic Acid". Journal of the American Chemical Society. 74: 253. doi:10.1021/ja01121a504.
  2. ^ Gadzikowska, M; Grynkiewicz, G (2002). "Tropane alkaloids in pharmaceutical and phytochemical analysis". Acta Poloniae Pharmaceutica. 59 (2): 149–60. PMID 12365608.


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