237817

D-(−)-Pantolactone

99%

• Synonym(s): (R)-(−)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone, (R)-(−)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone, (R)-(−)-Pantolactone, Pantoic acid γ-lactone
• Empirical Formula (Hill Notation): C₆H₁₀O₃
• CAS Number: 599-04-2
• Molecular Weight: 130.14
• Beilstein: 80957
• EC Number: 209-963-3
• MDL number: MFCD00005392
• UNSPSC Code: 12352005
• PubChem Substance ID: 24854272
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: 99%
• form: solid
• optical activity: [α]25/D −49.8°, c = 2 in H₂O
• bp: 120-122 °C/15 mmHg (lit.)
• mp: 91 °C (lit.)
• functional group: ester; hydroxyl
• SMILES string: CC1(C)COC(=O)[C@@H]1O
• InChI: 1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChI key: SERHXTVXHNVDKA-BYPYZUCNSA-N

Description

Application

D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.[1][2]
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.[3]
• (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.[4]
• A bicyclic diterpene named isofregenedadiol.[5]

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319
• Precautionary Statements: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves