301469
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
98%
Synonym(s):
S-Hothf, (S)-γ-Carboxy-γ-butyrolactone, (S)-5-Oxotetrahydro-2-furancarboxylic acid
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C5H6O4
CAS Number:
Molecular Weight:
130.10
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1424498
Assay:
98%
InChI
1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1
SMILES string
OC(=O)[C@@H]1CCC(=O)O1
InChI key
QVADRSWDTZDDGR-VKHMYHEASA-N
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
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
新产品
This item has
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service