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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:CHEBI:30765^N
ChemSpider	10274^N
ECHA InfoCard	100.008.201
EC Number	209-020-6
KEGG	C01456^N
MeSH	C011377
PubChem CID	10726
UNII	9RM4U80765^Y
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)^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
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). N verify (what is ^YN ?) 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]^[5]

References

^ ^a ^b Gadzikowska, M; Grynkiewicz, G (2002). "Tropane alkaloids in pharmaceutical and phytochemical analysis". Acta Poloniae Pharmaceutica. 59 (2): 149–60. PMID 12365608.
^ 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, 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.
^ 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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This page was last edited on 5 February 2024, at 16:00

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Synthesis

References