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55200

Sigma-Aldrich

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
Beilstein/REAXYS Number:
80957
EC Number:
209-963-3
MDL number:
MFCD00005392
UNSPSC Code:
12352005
PubChem Substance ID:
329758089

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

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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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

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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G.C. Fischer et al.
The Journal of Organic Chemistry, 50, 2011-2011 (1985)
R.E. Dolle et al.
Journal of the American Chemical Society, 107, 1691-1691 (1985)
P. Lavallee et al.
Tetrahedron Letters, 27, 679-679 (1986)
Dayong Si et al.
Applied microbiology and biotechnology, 95(2), 431-440 (2012-03-09)
The 1,2-propanediol (1,2-PD) inducible membrane-bound L-pantoyl lactone (L-PL) dehydrogenase (LPLDH) has been isolated from Rhodococcus erythropolis AKU2103 (Kataoka et al. in Eur J Biochem 204:799, 1992). Based on the N-terminal amino acid sequence of LPLDH and the highly conserved amino
Zhi-Hui Peng et al.
Organic letters, 4(17), 2945-2948 (2002-08-17)
[reaction: see text] The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this
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