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Merck
CN

55200

D-(−)-Pantolactone

puriss., ≥99.0% (T)

Synonym(s):

(R)-(−)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone, (R)-(−)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone, (R)-(−)-Pantolactone, Pantoic acid γ-lactone

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
599-04-2
Molecular Weight:
130.14
EC Number:
209-963-3
UNSPSC Code:
12352005
PubChem Substance ID:
329758089
Beilstein/REAXYS Number:
80957
MDL number:
MFCD00005392

Key Documents

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InChI key

SERHXTVXHNVDKA-BYPYZUCNSA-N

InChI

1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1

SMILES string

CC1(C)COC(=O)[C@@H]1O

grade

puriss.

assay

≥99.0% (T)

form

solid

optical activity

[α]20/D −51±2°, c = 3% in H2O

bp

120-122 °C/15 mmHg (lit.)

mp

89-92 °C, 91 °C (lit.)

storage temp.

2-8°C

Other Notes

Use as chiral building block: reduction to the triol; Amidation; Convenient acces to two enantiomeric oxiranes: S(+)- and R(-)-2,2-dimethyl-3,4-epoxybutanol

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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P. Lavallee et al.
Tetrahedron Letters, 27, 679-679 (1986)
R.E. Dolle et al.
Journal of the American Chemical Society, 107, 1691-1691 (1985)
G.C. Fischer et al.
The Journal of Organic Chemistry, 50, 2011-2011 (1985)
S L Miller et al.
Journal of molecular evolution, 36(4), 308-314 (1993-04-01)
Pantoic acid can by synthesized in good prebiotic yield from isobutyraldehyde or alpha-ketoisovaleric acid + H2CO + HCN. Isobutyraldehyde is the Strecker precursor to valine and alpha-ketoisovaleric acid is the valine transamination product. Mg2+ and Ca2+ as well as several
Optical resolution of pantolactone by a novel fungal enzyme, lactonohydrolase.
S Shimizu et al.
Annals of the New York Academy of Sciences, 799, 650-658 (1996-10-12)
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