Chemodex

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

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Product Details
Synonyms S-Hothf; (S)-γ-Carboxy-γ-butyrolactone; (S)-5-Oxotetrahydro-2-furancarboxylic acid
Product Type Chemical
Properties
Formula C5H6O4
MW 130.1
CAS 21461-84-7
Source/Host Chemicals Synthetic
Purity Chemicals ≥99% (GC)
Appearance White to off-white powder.
Solubility Soluble in methanol.
Identity Determined by 1H-NMR.
Declaration Manufactured by Chemodex.
Other Product Data

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Our product description may differ slightly from the original manufacturers product datasheet.

InChi Key QVADRSWDTZDDGR-VKHMYHEASA-N
Smiles O=C1CC[C@@H](C(O)=O)O1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +20°C
Handling Advice Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at RT.
Documents
Product Specification Sheet
Datasheet Download PDF
Description
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is a chiral lactone compound widely utilized in organic synthesis and medicinal chemistry. It serves as a versatile ligand for forming water-soluble silver(I) complexes, which exhibit notable antibacterial and antifungal properties. Additionally, this compound acts as a chiral resolving agent in the multi-step synthesis of phosphatidylinositol 3,5-bisphosphate, a crucial lipid involved in cellular signaling. Furthermore, it is employed in the preparation of municatacin analogs, which demonstrate cytotoxic activity against tumor cells, highlighting its potential in cancer research. Due to its unique structural features, (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is an essential intermediate in the development of biologically active compounds and chiral catalysts. This compound has also been described as a reversible proline dehydrogenase (PRODH) inhibitor.
Product References
(1) B. Figadere; Tetrahedr. Lett. 32, 7539 (1991) | (2) A.M. Riley & B.V.L. Potter; Tetrahedr. Lett. 39, 6769 (1998) | (3) K. Nomiya, et al.; J. Chem. Soc. Dalton Trans. 8, 1343 (2000) | (4) G.K. Scott, et al.; Mol. Cancer Ther. 18, 1374 (2019) | (5) G. Pallag, et al.; Int. J. Mol. Sci. 23, 5111 (2022)
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