| Identification | Back Directory | [Name]
(R)-4-Hydroxy-5-(hydroxymethyl)-3-(1-oxohexadecyl)-2(5H)-furanone | [CAS]
150627-37-5 | [Synonyms]
RK-682 >=98% (HPLC)
(R)-3-Hexadecanoyl-5-hydroxymethyltetronic acid
(±)-RK-682, protein tyrosine phosphatase inhibitor
(R)-4-Hydroxy-5-(hydroxymethyl)-3-(1-oxohexadecyl)-2(5H)-furanone
2(5H)-Furanone, 4-hydroxy-5-(hydroxymethyl)-3-(1-oxohexadecyl)-, (5R)- | [Molecular Formula]
C21H36O5 | [MDL Number]
MFCD20488046 | [MOL File]
150627-37-5.mol | [Molecular Weight]
368.51 |
| Chemical Properties | Back Directory | [Melting point ]
105-107 °C | [Boiling point ]
546.7±50.0 °C(Predicted) | [density ]
1.073±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO, heptane and xylene: ≥8mg/mL | [form ]
powder | [pka]
1.80±0.10(Predicted) | [color ]
white to tan | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
(±)-RK-682 (150627-37-5) is a protein tyrosine phosphatase inhibitor (IC50‘s = 54 7 μM for CD45, 2.0 μM for VHR; did not inhibit cdc25B) originally isolated from the fermentation of Streptomyces sp. 88-682.1?Inhibits cell cycle at G1/S. RK-682 has also been shown to inhibit PLA2 (IC50?= 16 μM)2, HIV-1 protease (IC50?= 84 μlM)3, and heparanase (IC50?= 17 μM)4. Natural RK-682 (R-isomer) and synthetic racemic material have identical phosphatase activity.5?Care should be taken when using RK-682 in the presence of metal salts – because it readily forms metal complexes that affects its phosphatase inhibitory activity.6?RK-682 has been identified as a potential promiscuous inhibitor.7 | [Uses]
RK 682 is a protein tyrosine phosphatase 1B (PTP1B) inhibitor, a potential therapeutic strategy for curing insulin resistance. | [References]
1) Hamaguchi?et al. (1995),?RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1?phase; FEBS Lett.,?372?54
2) Shinagawa?et al. (1993),?Tetronic acid derivatives, its manufacturing methods and uses; Jpn.Kokai Tokkyo Koho JP 05-43568,?35?1791
3) Roggo?et al. (1994),?3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin; new inhibitors of HIV-1 protease; J. Antibiot (Tokyo),?47?136
4) Ishida?et al. (2004),?Structure-based design of a selective heparanase inhibitor as an antimetastatic agent; Mol. Cancer Ther.,?3?1069
5) Sodeoka?et al1. (1996),?Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities; Tet. Lett.,?37?8775
6) Sodeoka?et al. (2001),?Asymmetric Synthesis of a 3-Acyltetronic Acid Derivative, RK-682, and Formation of Its Calcium Salt during Silica Gel Chromatography; Chem. Pharm. Bull.,?49?206
7) Carneiro?et al. (2015),?Is RK-682 a promiscuous enzyme inhibitor? Synthesis and in vitro evaluation of protein tyrosine phosphatase inhibition of racemic RK-682 and analogues; Eur. J. Med. Chem.,?97?42 |
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