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301469

Sigma-Aldrich

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H6O4
CAS Number:
21461-84-7
Molecular Weight:
130.10
Beilstein:
1424498
MDL number:
MFCD00064516
UNSPSC Code:
12352005
PubChem Substance ID:
24858189
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +14°, c = 5 in methanol

optical purity

ee: 99% (GLC)

bp

150-155 °C/0.2 mmHg (lit.)

mp

71-73 °C (lit.)

functional group

carboxylic acid
ester

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-/m0/s1

InChI key

QVADRSWDTZDDGR-VKHMYHEASA-N

General description

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is a chiral derivatizing agent for alcohols.

Application

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid may be used as a ligand to form water-soluble silver(I) complexes by reacting with silver oxide. These complexes show good antibacterial and antifungal activities. It may also be used a chiral resolving agent during the multi-step synthesis of phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P2].
Used to prepare municatacin analogs which show cytotoxic activity on tumor cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000120125
0000088728
0000065653
0000065654
BGBC3112V

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Hongde Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(6), 1353-1358 (2017-01-25)
L-2-hydroxyglutarate (L-2HG) has emerged as a putative oncometabolite that is capable of inhibiting enzymes involved in metabolism, chromatin modification, and cell differentiation. However, despite the ability of L-2HG to interfere with a broad range of cellular processes, this molecule is
l-a-Phosphatidyl-d-myo-inositol 3, 5-bisphosphate: total synthesis of a new inositol phospholipid via myo-inositol orthoacetate.
Riley AM and Potter BVL
Tetrahedron Letters, 39(37), 6769-6772 (1998)
Figadere, B.
Tetrahedron Letters, 32, 7539-7539 (1991)
Synthesis and crystal structure of three silver (I) complexes with (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid (S-Hothf) and its isomeric forms (R-Hothf and R, S-Hothf) showing wide spectra of effective antibacterial and antifungal activities. ....
Nomiya K, et al.
J. Chem. Soc., Dalton Trans., 8, 1343-1348 (2000)
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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