Vanadyl acetylacetonate
From Wikipedia, the free encyclopedia
| Vanadyl acetylacetonate | |
|---|---|
 |
|
| Other names | VO(acac)2 |
| Identifiers | |
| CAS number | [3153-26-2] |
| PubChem | |
| Properties | |
| Molecular formula | C10H14O5V |
| Molar mass | 265.16 |
| Appearance | blue-green |
| Melting point |
256-259 °C (dec.) |
| Solubility in water | CHCl3, CH2Cl2, Benzene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Vanadyl(acetylacetonate) is the chemical compound with the formula VO(C5H7O2)2. This blue-green coordination complex consists of the vanadyl group, VO2+, bound to two acetylacetonate anions, acac−. Like other charge-neutral acetylacetonates, this complex is soluble in organic solvents.
Contents |
[edit] Synthesis
The complex is prepared from vanadium(IV) or vanadium(V) precursors, the latter being more convenient:[1]
[edit] Structure and properties
The complex has a square pyramidal structure with a short V=O bond. This d1 compound is paramagnetic. Its optical spectrum exhibits two transitions. It is a weak Lewis acid, forming adducts with pyridine and methylamine.[1]
[edit] Applications
It is used in organic chemistry as a reagent in the epoxidation of allylic alcohols in combination with tert-butylhydroperoxide (TBHP). The VO(acac)2-TBHP system is exclusively epoxidizes geraniol at the allylic alcohol position. For comparison, another epoxidizing agent m-CPBA, reacts exclusively with the other alkene group. TBHP oxidizes VO(acac)2 to a vanadium(V) species which coordinates the alcohol of the substrate and the hydroperoxide.[2]
[edit] Biomedical aspects
Vanadyl(acac) exhibits insulin mimetic properties, in that in can stimulate the phosphorylation of protein kinase B (PKB/Akt) and glycogen synthase kinase-3 (GSK3)[3]. It has also been shown inhibit tyrosine phosphatase(PTPase), PTPases such as PTP1B, which dephosphorylates insulin receptor beta subunit, thus increasing its phosphorylation, allowing for a prolonged activation of IRS-1, PKB, and GSK3, allowing them to exert their anti-diabetic properties[3].
[edit] External links
[edit] References
- ^ a b Richard A. Rowe, Mark M. Jones, Burl E. Bryant, W. Conard Fernelius "Vanadium(IV) Oxy(acetylacetonate)" Inorganic Syntheses, 1957, volume 5, pp. 113-116.
- ^ Takashi Itoh, Koichiro Jitsukawa, Kiyotomi Kaneda, Shiichiro Teranishi (1979). "Vanadium-catalyzed epoxidation of cyclic allylic alcohols. Stereoselectivity and stereocontrol mechanism". J. Am. Chem. Soc. 101 (1): 159–169. doi:.
- ^ a b Mohamad Z. Mehdi and Ashok K. Srivastava (2005). "Organo-vanadium compounds are potent activators of the protein kinase B signaling pathway and protein tyrosine phosphorylation: Mechanism of insulinomimesis". ABB 440: 158–164. doi:.
