All Photos(2)
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:
Molecular Weight:
130.14
Beilstein:
80957
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.)
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
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Related Categories
Application
D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.
It can be used as a chiral starting material to synthesize:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Total synthesis of isofregenedadiol
Kurhade SE, et al.
Organic Letters, 13(14), 3690-3693 (2011)
Asymmetric diels alder reactions and michael type additions with 6 (R)-3′(R)-Pantolactone-substituted-2H-pyran-3 (6H)-one.
Knol J, et al.
Tetrahedron Letters, 32(50), 7465-7468 (1991)
Matthew B Kubilius et al.
ACS omega, 2(11), 8308-8312 (2017-11-21)
1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide (EDC) is a commonly used reagent for bioconjugation and peptide synthesis. Both EDC and the corresponding urea derivative, 1-(3-dimethylaminopropyl)-3-ethylurea (EDU), are achiral. As the reagent is active in aqueous solutions, it is a common choice for the study of
Enantiospecific synthesis of sex pheromone of the obscure mealybug from pantolactone via tandem conjugate addition/cyclization
Hajare AK, et al.
Tetrahedron Letters, 51(40), 5291-5293 (2010)
Diastereoface-discriminative metal coordination in asymmetric synthesis: d-pantolactone as practical chiral auxiliary for Lewis acid catalyzed Diels-Alder reactions
Poll T, et al.
Tetrahedron Letters, 26(26), 3095-3098 (1985)
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