Tropic acid

Tropic acid
Names
	IUPAC name 3-Hydroxy-2-phenylpropanoic acid
	Other names 2-Phenylhydracrylic acid; Tropate
Identifiers
CAS Number	529-64-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:CHEBI:30765 ;
ChemSpider	10274 ;
ECHA InfoCard	100.008.201
EC Number	209-020-6;
KEGG	C01456 ;
MeSH	C011377
PubChem CID	10726;
CompTox Dashboard (EPA)	DTXSID90862179 ;
	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	166.176 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

^ ^a ^b Template:Cite PMID
^ Sletzinger, Paulsen, U.S. patent 2,390,278 (1945 to Merck & Co.).
^ Blicke, U.S. patent 2,716,650 (1955 to University of Michigan).
^ DE 923426 (1955 to Sterling Drug).

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[Gadzikowska-1] Template:Cite PMID

[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).

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