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310476

Sigma-Aldrich

(R)-(−)-5-Oxo-2-tetrahydrofurancarboxylic acid

98%

Synonym(s):

(R)-γ-Carboxy-γ-butyrolactone, (R)-5-Oxotetrahydro-2-furancarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H6O4
CAS Number:
53558-93-3
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1424499
MDL number:
MFCD00011567
UNSPSC Code:
12352005
PubChem Substance ID:
24858796
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]20/D −14°, c = 5 in methanol

optical purity

ee: 97% (GLC)

bp

165-167 °C/0.3 mmHg (lit.)

mp

71-73 °C (lit.)

SMILES string

OC(=O)[C@H]1CCC(=O)O1

InChI

1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m1/s1

InChI key

QVADRSWDTZDDGR-GSVOUGTGSA-N

General description

(R)-(−)-5-Oxo-2-tetrahydrofurancarboxylic acid belongs to the class of furans, considered as heterocyclic building blocks. It is used as an HPLC derivatization reagent for UV/Vis detection.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Shinji K Strain et al.
Rapid communications in mass spectrometry : RCM, 33(17), 1401-1409 (2019-05-31)
2-Hydroxyglutarate (2-hg) exists as enantiomers and can readily undergo cyclization to its lactone. Gas chromatography/electron ionization mass spectrometry (GC/EI-MS) has been used to separate 2-hg enantiomers in bodily fluids but the assay cannot simultaneously measure cyclic and acylic 2-hg enantiomers.

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