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
Empirical Formula (Hill Notation):
C5H6O4
CAS Number:
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1424498
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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.)

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

Related Categories

General description

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

Application

Used to prepare municatacin analogs which show cytotoxic activity on tumor cells.
(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].

Packaging

1, 5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
Figadere, B.
Tetrahedron Letters, 32, 7539-7539 (1991)
Chaitanya A Kulkarni et al.
eLife, 9 (2020-08-17)
Alkb homolog 7 (ALKBH7) is a mitochondrial α-ketoglutarate dioxygenase required for DNA alkylation-induced necrosis, but its function and substrates remain unclear. Herein, we show ALKBH7 regulates dialdehyde metabolism, which impacts the cardiac response to ischemia-reperfusion (IR) injury. Using a multi-omics...
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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