D-(-)-PANTOLACTONE

Chemical properties

WHITE CRYSTALLINE POWDER OR CRYSTALS

The Uses of D-(-)-PANTOLACTONE

D-(-)-PANTOLACTONE is an important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia.

The Uses of D-(-)-PANTOLACTONE

D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.
It can be used as a chiral starting material to synthesize:

• An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.
• (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.
• A bicyclic diterpene named isofregenedadiol.

Definition

ChEBI: (R)-pantolactone is a butan-4-olide that is dihydrofuran-2(3H)-one substituted by a hydroxy group at position 3 and two methyl groups at position 4 (the R-stereoisomer). It has a role as a Saccharomyces cerevisiae metabolite. It is functionally related to a (R)-pantoic acid.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Purification Methods

Recrystallise the lactone from Et2O/pet ether, diisopropyl ether or *C6H6/pet ether and sublime it at 25o/0.0001mm. It hydrolyses readily to the hydroxy-acid and racemises when heated above 145o. The Brucine salt has m 211-212o (from EtOH). [Kuhn & Wieland Chem Ber 73 1134 1940, and Stiller et al. J Am Chem Soc 62 1779 1940, Bental & Tishler J Am Chem Soc 68 1463 1946, Beilstein 18/1 V 22.]