Specifications
- Purity
- ≥99% (GC)
- Appearance
- White to off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- Soluble in methanol.
- Melting Point
- 71-73 °C (lit.)
- Boiling Point
- 150-155 °C/0.2 mmHg (lit.)
- Optical Activity
- [α]20/D +14°, c = 5 in methanol
Available from stock
(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid
- SKU
- O0227
Category: API's & Intermediates
- Synonyms
- S-Hothf, (S)-&gamma,-Carboxy-&gamma,-butyrolactone, (S)-5-Oxotetrahydro-2-furancarboxylic acid
- 21461-84-7
- CAS-Number
- C5H6O4
- Molecular Formula
- 130.10
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- Shipping
- AMBIENT
- Short Term Storage
- RT
- Long Term Storage
- RT
- Handling Advice
- Protect from light and moisture.
- Use / Stability
- Stable for at least 2 years after receipt when stored at RT.
- Transportation
- Not dangerous goods
- 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.
- Smiles
- O=C1CC[C@@H](C(O)=O)O1
- InChi Key
- QVADRSWDTZDDGR-VKHMYHEASA-N
- 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)
- InChi
- InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1
(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.
Additional information
| Synonyms | S-Hothf, (S)-&gamma,-Carboxy-&gamma,-butyrolactone, (S)-5-Oxotetrahydro-2-furancarboxylic acid |
|---|---|
| Purity | ≥99% (GC) |
| Appearance | White to off-white powder |
| CAS-Number | 21461-84-7 |
| Molecular Formula | C5H6O4 |
| Molecular Weight | 130.10 |
| Identity | 1H-NMR |
| Solvents | Soluble in methanol. |
| Melting Point | 71-73 °C (lit.) |
| Boiling Point | 150-155 °C/0.2 mmHg (lit.) |
| Optical Activity | [α]20/D +14°, c = 5 in methanol |
| Smiles | O=C1CC[C@@H](C(O)=O)O1 |
| InChi Key | QVADRSWDTZDDGR-VKHMYHEASA-N |
| Shipping | AMBIENT |
| Short Term Storage | RT |
| Long Term Storage | RT |
| Handling Advice | Protect from light and moisture. |
| Use / Stability | Stable for at least 2 years after receipt when stored at RT. |
| Transportation | Not dangerous goods |
| 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) |
| InChi | InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1 |
| Quantity | 1 g, 5 g, Bulk |
