Tropic acid

Tropic acid

Names
IUPAC name 3-Hydroxy-2-phenylpropanoic acid
Other names 2-Phenylhydracrylic acid; Tropate
Identifiers
CAS Number	529-64-6
ChEBI	CHEBI:CHEBI:30765
ChemSpider	10274
EC Number	209-020-6
Jmol interactive 3D	Image
KEGG	C01456
MeSH	C011377
PubChem	10726
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) Key: JACRWUWPXAESPB-UHFFFAOYSA-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
SMILES C1=CC=C(C=C1)C(CO)C(=O)O
Properties
Chemical formula	C9H10O3
Molar mass	166.18 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

Pharmaceutical Uses

• Tropic acid is reacted with tropine (product of tropinone) to produce atropine (cf. Homatropine).
• Scopine is reacted with tropic acid in a Fischer esterification to produce scopolamine also.
• Other examples: tropicamide, Anisodamine.
• Quats: Hyoscine butylbromide, Butropium bromide (Coliopan®), Fentonium, Methylatropine, methscopolamine.

References

1. 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  (1955 to Sterling Drug).