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 ;
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;
UNII	9RM4U80765 ;
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][5]

Drugs

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.
tropicamide
Anisodamine.
Quats: Hyoscine butylbromide, Butropium bromide (Coliopan®), Fentonium, Methylatropine, methscopolamine, Cimetropium.
Eucatropine
Amprotropine
Tropesin [65189-78-8] [65828-79-7].
Pimetremide
Ipragratine
Solandrine (Norhyoscyamine)

References

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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[Gadzikowska-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, 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.