Pantolactone

Structural formula
	Structural formula of pantolactone without information on stereochemistry
General
Surname	Pantolactone
other names	β, β- dimethyl-α-hydroxy-γ-butyrolactone; DL pantolactone; Dihydro-3-hydroxy-4,4-dimethyl-2 (3 H ) -furanone;
Molecular formula	C 6 H 10 O 3
Brief description	colorless solid
External identifiers / databases
EC number	201-210-7
ECHA InfoCard	100.001.101
PubChem	989
ChemSpider	964
Wikidata	Q22829045
properties
Molar mass	130.14 g mol −1
Physical state	firmly
density	1.25 g cm −3
Melting point	74-78 ° C (racemate); 92 ° C ( R- form);
boiling point	120–122 ° C (20 hPa, R -form)
solubility	soluble in water
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 .

Pantolactone is a chemical compound from the group of substituted lactones .

Isomers

Pantolactone contains a stereocenter , so it is chiral and occurs in two enantiomeric forms , ( R ) -pantolactone and ( S ) -pantolactone. Racemic pantolactone [synonym: ( RS ) -pantolactone] is a 1: 1 mixture of the ( R ) - and the ( S ) -enantiomer.

Isomers of pantolactone
Surname	( S ) -pantolactone	( R ) -pantolactone
other names	(+) - pantolactone	(-) - pantolactone
Structural formula
CAS number	5405-40-3	599-04-2
	79-50-5 (racemate)
EC number	626-470-2	209-963-3
	201-210-7 (racemate)
ECHA info card	100.149.096	100.009.059
	100.001.101 (racemate)
PubChem	736053	439368
	989 (racemate)
Wikidata	Q76962655	Q27102042
	Q22829045 (racemate)

Occurrence

Pantolactone is found in wine and sherry flavor.

Extraction and presentation

( R ) -Pantolactone is obtained by degrading pantothenic acid or by enantioselective reduction of the corresponding oxolactone . Both stereoisomers can be isolated separately by resolution with ( R ) - and ( S ) - phenylethanamine .

properties

Pantolactone is a colorless solid that is soluble in water.

use

In addition to being used as a chiral auxiliary for diastereoselective Diels-Alder reactions , ( R ) -pantolactone is used as a synthetic building block from the so-called “chiral pool”, for example for the synthesis of bryostatin and the antibiotic elfamycin . It is also used as a humectant in the cosmetics industry.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g data sheet DL-α-Hydroxy-β, β-dimethyl-γ-butyrolactone, purum, ≥97.0% (T) from Sigma-Aldrich , accessed on October 19, 2019 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f Entry on pantolactone. In: Römpp Online . Georg Thieme Verlag, accessed on October 19, 2019.
↑ Joachim Paust, Sigberg Pfohl, Werner Reif, Wolfram Schmidt: Racemate resolution of pantolactone with new chiral amines. In: Justus Liebig's Annals of Chemistry. 1978, 1978, p. 1024, doi : 10.1002 / jlac.197819780612 .
↑ Paul Präve: Handbook of biotechnology . Oldenbourg Industrieverlag, 1994, ISBN 978-3-8356-6223-0 , p. 719 ( limited preview in Google Book search).
↑ dr-pfleger.de: INCI-Lexikon - Service for Patients - Products - dr-pfleger.de , accessed on October 19, 2019

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet DL-α-Hydroxy-β, β-dimethyl-γ-butyrolactone, purum, ≥97.0% (T) from Sigma-Aldrich , accessed on October 19, 2019 ( PDF ).

[RömppOnline-2] ↑ ^a ^b ^c ^d ^e ^f Entry on pantolactone. In: Römpp Online . Georg Thieme Verlag, accessed on October 19, 2019.

[DOI10.1002/jlac.197819780612-3] Joachim Paust, Sigberg Pfohl, Werner Reif, Wolfram Schmidt: Racemate resolution of pantolactone with new chiral amines. In: Justus Liebig's Annals of Chemistry. 1978, 1978, p. 1024, doi : 10.1002 / jlac.197819780612 .

[Paul_Präve-4] Paul Präve: Handbook of biotechnology . Oldenbourg Industrieverlag, 1994, ISBN 978-3-8356-6223-0 , p. 719 ( limited preview in Google Book search).

[dr-pfleger.de-5] r-pfleger.de: INCI-Lexikon - Service for Patients - Products - dr-pfleger.de , accessed on October 19, 2019