Tropic acid

Structural formula
	Structural formula without stereochemistry
General
Surname	Tropic acid
other names	2-phenylhydracrylic acid; 3-hydroxy-2-phenylpropionic acid;
Molecular formula	C 9 H 10 O 3
Brief description	colorless to beige solid
External identifiers / databases
EC number	209-020-6
ECHA InfoCard	100.008.201
PubChem	10726
ChemSpider	10274
Wikidata	Q2823318
properties
Molar mass	166.17 g mol −1
Physical state	firmly
Melting point	116-118 ° C ( racemate ); 129–130 ° C ( R and S shape);
solubility	soluble in water and benzene; soluble in ethanol and ether;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tropic acid is a chemical compound from the group of carboxylic acids and a component of some tropane alkaloids .

Extraction and presentation

Tropic acid can best be obtained by the reaction of acetophenone cyanohydrin via 2-phenyllactic acid , atropic acid and chlorohydro tropic acid followed by hydrolysis . (-) - (S) - or (±) -Tropasäure is in the saponification of (-) - hyoscyamine , atropine , scopolamine and other tropane - alkaloids in which tropic acid is present esterified obtained. The formation of tropic acid was discovered in 1864 when atropine was boiled with barite water .

Tropic acid synthesis 1

Tropic acid synthesis 2

Synthesis:

properties

Tropic acid is an almost odorless, colorless to beige solid that is soluble in water. When heated or by enzymatic hydrolysis, atropic acid is formed through elimination of water .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet Tropic acid, 98% from Sigma-Aldrich , accessed on June 4, 2016 ( PDF ).
^ J. Buckingham: Dictionary of Organic Compounds . CRC Press, 1986, ISBN 978-0-412-54090-5 , pp. 3807 ( limited preview in Google Book Search).
^ ^A ^b ^c W. LF Armarego, Christina Li Lin Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2013, ISBN 0-12-382161-4 , pp. 395 ( limited preview in Google Book search).
↑ ^a ^b Entry on tropic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 4, 2016.
^ H. Altenburg, I. Bang, K. Bartelt, Fr. Baum, C. Brahm, W. Cramer, K. Dieterich, R. Ditmar, M. Dohrn, H. Einbeck, H. Euler, ES Faust, C. Funk, O. v. Fürth, O. Gerngroß: Biochemisches Handlexikon V. Volume . Springer-Verlag, 2013, ISBN 978-3-642-90815-6 , pp. 79 ( limited preview in Google Book search).
↑ ^a ^b M. Gadzikowska, G. Grynkiewicz: Tropane alkaloids in pharmaceutical and phytochemical analysis. In: Acta Pol Pharm. 59, pp. 149-160, PMID 12365608 .
↑ Sletzinger, Paulsen, US patent 2390278 (1945 to Merck & Co. ).
↑ Views, US patent 2716650 (1955 to University of Michigan ).
↑ Patent 923426 (1955 to Sterling Drug ).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet Tropic acid, 98% from Sigma-Aldrich , accessed on June 4, 2016 ( PDF ).

[J._Buckingham-2] J. Buckingham: Dictionary of Organic Compounds . CRC Press, 1986, ISBN 978-0-412-54090-5 , pp. 3807 ( limited preview in Google Book Search).

[W._L._F._Armarego,_Christina_Li_Lin_Chai-3] A ^b ^c W. LF Armarego, Christina Li Lin Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2013, ISBN 0-12-382161-4 , pp. 395 ( limited preview in Google Book search).

[RömppOnline-4] Entry on tropic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 4, 2016.

[H._Altenburg,_I._Bang,_K._Bartelt,_Fr._Baum,_C._Brahm,_W._Cramer,_K._Dieterich,_R._Ditmar,_M._Dohrn,_H._Einbeck,_H._Euler,_E.S._Faust,_C._Funk,_O._v._Fürth,_O._Gerngroß-5] H. Altenburg, I. Bang, K. Bartelt, Fr. Baum, C. Brahm, W. Cramer, K. Dieterich, R. Ditmar, M. Dohrn, H. Einbeck, H. Euler, ES Faust, C. Funk, O. v. Fürth, O. Gerngroß: Biochemisches Handlexikon V. Volume . Springer-Verlag, 2013, ISBN 978-3-642-90815-6 , pp. 79 ( limited preview in Google Book search).

[PMID12365608-6] M. Gadzikowska, G. Grynkiewicz: Tropane alkaloids in pharmaceutical and phytochemical analysis. In: Acta Pol Pharm. 59, pp. 149-160, PMID 12365608 .

[7] Sletzinger, Paulsen, US patent 2390278 (1945 to Merck & Co. ).

[8] Views, US patent 2716650 (1955 to University of Michigan ).

[9] Patent 923426 (1955 to Sterling Drug ).