D-(-)-PANTOLACTONE Chemical Properties

Melting point:

91 °C(lit.)

Boiling point:

120-122 °C15 mm Hg(lit.)

Density 

1.1066 (rough estimate)

vapor pressure 

0.3-3.28Pa at 15-35℃

refractive index 

-50.8 ° (C=2, H2O)

Flash point:

120-122°C/15mm

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)

pka

13.12±0.40(Predicted)

form 

Crystals or Crystalline Powder

color 

White

Odor

cotton candy

optical activity

[α]25/D 49.8°, c = 2 in H2O

Water Solubility 

almost transparency

Sensitive 

Hygroscopic

Merck 

14,7013

BRN 

80957

InChIKey

SERHXTVXHNVDKA-BYPYZUCNSA-N

LogP

-0.973--0.46 at 22.5-25℃ and pH7.1

CAS DataBase Reference

599-04-2(CAS DataBase Reference)

EPA Substance Registry System

Pantolactone (599-04-2)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

1

F 

3-10

TSCA 

Yes

HS Code 

29322090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

D-(-)-PANTOLACTONE Usage And Synthesis

Chemical Properties

WHITE CRYSTALLINE POWDER OR CRYSTALS

Uses

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.

Uses

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.

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.]

D-(-)-PANTOLACTONE(599-04-2)Related Product Information

• H-BETA-ALA-BETA-ALA-OH
• (2S)-2,4-Dihydroxy-3,3-dimethylbutanoic acid
• (R)-Methyl 3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate
• Vitamin B5 Impurity 1
• 3,3-BIS(N,N-DIPROPANOIC ACID)
• DL-Pantolactone
• PICROTOXIN
• L-Pantolactone, (S)-(+)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone,(S)-(+)-PANTOLACTONE,L-PANTOLACTONE
• ALPHA-HYDROXY-GAMMA-BUTYROLACTONE
• Bilobalide
• GINKGOLIDEM
• Ginkgolide A
• Ginkgolide J
• PICROTOXININ
• Ginkgolide B
• Ginkgolide C
• PICROTIN
• Gamma Butyrolactone