Mandelic acid

Structural formula
	Structure without specifying the stereochemistry
General
Surname	Mandelic acid
other names	Hydroxyphenylacetic acid; Phenylglycolic acid; MANDELIC ACID ( INCI ) ;
Molecular formula	C 8 H 8 O 3
Brief description	colorless crystals
External identifiers / databases
EC number	202-007-6
ECHA InfoCard	100.001.825
PubChem	1292
ChemSpider	1253
Wikidata	Q412293
properties
Molar mass	152.15 g mol −1
Physical state	firmly
density	1.30 g cm −3
Melting point	119 ° C [( RS ) -mandelic acid]; 133 ° C (enantiomerically pure);
pK s value	3.37 (25 ° C)
solubility	soluble in water (158.7 g l −1 at 20 ° C); soluble in diethyl ether , ethanol and isopropanol ;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 318
	P: 260-280-305 + 351 + 338-313
Toxicological data	300 mg kg −1 ( LD 50 , rat , im )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The mandelic acid (α-hydroxyphenylacetic acid) is a chemical compound from the group of aromatic carboxylic acids .

Isomers

Due to the stereocenter at the α-C atom, mandelic acid forms two enantiomers , D - (-) - and L - (+) - mandelic acid [synonyms: ( R ) - and ( S ) -mandelic acid].

Isomers of mandelic acid
Surname	( R ) -mandelic acid	( S ) -mandelic acid
other names	D - (-) - mandelic acid	L - (+) - mandelic acid
Structural formula
CAS number	611-71-2	17199-29-0
	90-64-2 (mixture)
EC number	210-276-6	241-240-8
	202-007-6 (mixture)
ECHA info card	100.009.343	100.037.476
	100.001.825 (mixture)
PubChem	11914	439616
	1292 (mixture)
DrugBank	-	DB2280
	- (mixture)
Wikidata	Q63390533	Q27096314
	Q412293 (mixture)

Synthesis and manufacture

Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) when he heated amygdalin , an extract from bitter almonds , with dilute hydrochloric acid . Mandelic acid is obtained industrially from benzaldehyde and hydrocyanic acid in order to be further processed in various medicines.

The biotechnological production of 4-hydroxy-mandelic acid and mandelic acid on the basis of glucose was demonstrated with the help of a genetically modified yeast Saccharomyces cerevisiae , whereby the naturally occurring hydroxymandelate synthase in the bacterium Amycolatopsis is incorporated into a wild-type strain of yeast, partially changed by the exchange of a gene sequence and was expressed .

properties

It is a white, crystalline solid.

effect

Mandelic acid has a bacteriostatic or bactericidal effect on streptococci , staphylococci and coli bacteria in an acidic environment .

Too high styrene burdens in the breath values mandelic acid in the urine are reflected in the occupational medical diagnostics (plastic production) as high down.

use

( R ) - or ( S ) -mandelic acid is also used in asymmetric aldol reactions and serves as a chiral ligand. ( R ) -Mandelic acid forms diastereomeric salts with racemic amines, which can often be separated by fractional crystallization. The respective enantiomerically pure amine can then be obtained therefrom by adding a base. With this method, for example, the resolution of the drug ( RS ) - penbutolol has been successful. ( S ) -Mandelic acid can also be used as a reagent for the resolution of racemic amines.

Web links

Wiktionary: mandelic acid - explanations of meanings, word origins, synonyms, translations

Individual evidence

↑ entry to Mandelic ACID in CosIng database of the European Commission, accessed on 13 August 2020th
↑ ^a ^b ^c ^d Entry on mandelic acid. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2014.
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 989.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-48.
↑ Data sheet mandelic acid at AlfaAesar, accessed on June 7, 2010 ( PDF )(JavaScript required) .
↑ ^a ^b Entry on mandelic acid in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Entry on Mandelic acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on January 11, 2020.
↑ Mara Reifenrath, Eckhard Boles: Engineering of hydroxymandelate synthases and the aromatic amino acid pathway enables de novo biosynthesis of mandelic and 4-hydroxymandelic acid with Saccharomyces cerevisiae. Metabolic Engineering January 45, 2018; Pp. 246-254. doi : 10.1016 / j.ymben.2018.01.001 .
↑ AWMF online work under the influence of benzene, its homologues or styrene ( Memento from September 30, 2007 in the Internet Archive ).
↑ Rainer Mahrwald: Titanium (IV) alkoxides Ligand Exchange with α-Hydroxy Acids: The Enantioselective aldol addition. In: Organic Letters. 2, 2000, pp. 4011-4012, doi : 10.1021 / ol0002727 .
↑ Hermann J. Roth , Christa E. Müller and Gerd Folkers: Stereochemie & Arzneimittel, Wissenschaftliche Verlagsgesellschaft Stuttgart, 1998, ISBN 3-8047-1485-4 , pp. 164-165.

[CosIng-1] try to Mandelic ACID in CosIng database of the European Commission, accessed on 13 August 2020th

[roempp-2] Entry on mandelic acid. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2014.

[MerckIndex-3] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 989.

[CRC90_8_48-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-48.

[alfa-5] Data sheet mandelic acid at AlfaAesar, accessed on June 7, 2010 ( PDF )(JavaScript required) .

[GESTIS-6] Entry on mandelic acid in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[7] Entry on Mandelic acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on January 11, 2020.

[Reifenrath_&_Boles_2018-8] Mara Reifenrath, Eckhard Boles: Engineering of hydroxymandelate synthases and the aromatic amino acid pathway enables de novo biosynthesis of mandelic and 4-hydroxymandelic acid with Saccharomyces cerevisiae. Metabolic Engineering January 45, 2018; Pp. 246-254. doi : 10.1016 / j.ymben.2018.01.001 .

[9] AWMF online work under the influence of benzene, its homologues or styrene ( Memento from September 30, 2007 in the Internet Archive ).

[10] Rainer Mahrwald: Titanium (IV) alkoxides Ligand Exchange with α-Hydroxy Acids: The Enantioselective aldol addition. In: Organic Letters. 2, 2000, pp. 4011-4012, doi : 10.1021 / ol0002727 .

[Roth-11] Hermann J. Roth , Christa E. Müller and Gerd Folkers: Stereochemie & Arzneimittel, Wissenschaftliche Verlagsgesellschaft Stuttgart, 1998, ISBN 3-8047-1485-4 , pp. 164-165.