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| | D-(-)-PANTOLACTONE Basic information |
| | 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) | | 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 Statements | 22-24/25 | | WGK Germany | 1 | | F | 3-10 | | TSCA | Yes | | HS Code | 29322090 |
| | 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 Preparation Products And Raw materials |
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