| Identification | More | [Name]
D-(-)-PANTOLACTONE | [CAS]
599-04-2 | [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 | [EINECS(EC#)]
209-963-3 | [Molecular Formula]
C6H10O3 | [MDL Number]
MFCD00005392 | [Molecular Weight]
130.14 | [MOL File]
599-04-2.mol |
| Chemical Properties | Back Directory | [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 | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [F ]
3-10 | [TSCA ]
Yes | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [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.] |
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