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 ☒N
ChemSpider
  • 10274 ☒N
ECHA InfoCard 100.008.201 Edit this at Wikidata
EC Number
  • 209-020-6
KEGG
  • C01456 ☒N
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) ☒N
    Key: JACRWUWPXAESPB-UHFFFAOYSA-N ☒N
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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 synthesis 1:[1] Tropic acid synthesis 2:[1]

Prepn:[2][3][4][5]

References

  1. ^ a b Gadzikowska, M; Grynkiewicz, G (2002). "Tropane alkaloids in pharmaceutical and phytochemical analysis". Acta Poloniae Pharmaceutica. 59 (2): 149–60. PMID 12365608.
  2. ^ Sletzinger, Paulsen, U.S. patent 2,390,278 (1945 to Merck & Co.).
  3. ^ Blicke, U.S. patent 2,716,650 (1955 to University of Michigan).
  4. ^ DE 923426, Blicke, Frederick Franklin, "Verfahren zur Herstellung von α-substituierten β-Oxypropionsäuren [Process for the preparation of α-substituted β-oxypropionic acids]", published 1955-02-14, assigned to Sterling Drug Inc. 
  5. ^ Blicke, F. F., Raffelson, H., Barna, B. (January 1952). "The Preparation of Tropic Acid". Journal of the American Chemical Society. 74 (1): 253–253. doi:10.1021/ja01121a504.


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