599-04-2

Name	D-(-)-PANTOLACTONE
CAS	599-04-2
EINECS(EC#)	209-963-3
Molecular Formula	C6H10O3
MDL Number	MFCD00005392
Molecular Weight	130.14
MOL File	599-04-2.mol

Synonyms

2,4-DIHYDROXY-3,3-DIMETHYLBUTYRIC ACID GAMMA-LACTONE ALPHA-HYDROXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE D-1-HYDROXY-2,2-DIMETHYL-3-BUTYROLACTONE D-(-)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE D-ALPHA-HYDROXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE D-(-)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE D-PANTOIC ACID G-LACTONE (-)-D-PANTOLACTONE D-(-)-PANTOLACTONE D-PANTOLACTONE D-(-)-PANTOYL LACTONE D-PANTOYL LACTONE PANTOIC ACID GAMMA-LACTONE PANTOLACTONE PANTOLACTONE-D R(-)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE R(-)-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE (R)-(-)-ALPHA-HYDROXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE (R)-(-)-BETA,BETA-DIMETHYL-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE (R)-(-)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE

Chemical Properties

Appearance	WHITE CRYSTALLINE POWDER OR CRYSTALS
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)
Fp	120-122°C/15mm
storage temp.	2-8°C
solubility	Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)
form	Crystals or Crystalline Powder
pka	13.12±0.40(Predicted)
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 Data

Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	1
F	3-10
TSCA	Yes
HS Code	29322090

Raw materials And Preparation Products

Hazard Information

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.]

Spectrum Detail

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