301469
(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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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C5H6O4
CAS Number:
Molecular Weight:
130.10
Beilstein/REAXYS Number:
1424498
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.[1]
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.[1] It may also be used a chiral resolving agent during the multi-step synthesis of phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P2].[2]
Used to prepare municatacin analogs which show cytotoxic activity on tumor cells.[3]
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
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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)
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)
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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