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55201

Sigma-Aldrich

DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone

purum, ≥97.0% (T)

Synonym(s):

β,β-Dimethyl-α-hydroxy-γ-butyrolactone, DL-Pantolactone, Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
79-50-5
Molecular Weight:
130.14
Beilstein:
80958
EC Number:
201-210-7
MDL number:
MFCD00064333
UNSPSC Code:
12352100
PubChem Substance ID:
329758090
NACRES:
NA.22

grade

purum

Quality Level

100

Assay

≥97.0% (T)

form

solid

mp

74-78 °C (lit.)

solubility

H2O: 1 g/10 mL, clear, colorless to almost colorless

functional group

ester
hydroxyl

SMILES string

CC1(C)COC(=O)C1O

InChI

1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3

InChI key

SERHXTVXHNVDKA-UHFFFAOYSA-N

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Application

DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone (DL-pantolactone) may be used in the preparation of 3,5-dinitrobenzoyl-DL-pantolactone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

251.6 °F - open cup

Flash Point(C)

122 °C - open cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6277
BCCG3059
BCCD7932
BCCC5325
BCBZ8825

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Sigma-Aldrich

H5501

Methyl 4-hydroxybenzoate

D-Panthenol ≥98.0% (NT)

Sigma-Aldrich

76200

D-Panthenol

The Bacterial Degradation of Pantothenic Acid. III. Enzymatic Formation of Aldopantoic Acid*.
Goodhue CT and Snell EE.
Biochemistry, 5(2), 403-408 (1966)
A G Moĭseenok et al.
Voprosy meditsinskoi khimii, 30(1), 126-128 (1984-01-01)
A gas chromatographic procedure is described for quantitative estimation of alpha-hydroxy-beta 1 beta-dimethyl-gamma-butyrolactone (pantolactone). The chromatography was carried out using "LHM-8MD" apparatus equipped with a flame ionization detector. Columns with chromaton N-AW modified by 5% silicone XE-60 were used, helium
Keiji Sakamoto et al.
Journal of biotechnology, 118(1), 99-106 (2005-06-07)
We developed an enzymatic resolution system for DL-pantoyl lactone that uses immobilized mycelia of Fusarium oxysporum, which produce a lactone-hydrolyzing enzyme (lactonase). The lactonase catalyzes the stereospecific hydrolysis of D-pantoyl lactone. One hundred eighty repeated batch reactions (total reaction time
Atul K Hajare et al.
The Journal of organic chemistry, 76(3), 963-966 (2011-01-05)
An efficient synthesis of potent molluscicidal agent cyanolide A, a glycosidic 16-membered macrolide, starting from D-(-)-pantolactone is reported. Highly stereoselective aldol, oxa-Michael addition, and Yamaguchi macrolactonization are the key steps in the present synthesis.
Bing Chen et al.
Applied biochemistry and biotechnology, 162(3), 744-756 (2009-10-31)
The levo-lactonase gene of Fusarium proliferatum ECU2002 (EC3.1.1.25) was cloned and expressed in Escherichia coli JM109 (DE3) for biocatalytic resolution of industrially important chiral lactones, including DL-pantoyl lactone which was a key precursor to calcium D-pantothenate. By increasing the biomass
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