1646 Vanadyl acetylacetonate Vanadyl acetylacetonate is a coordination complex of vanadium. It is used in organic chemistry as a reagent in the epoxidation of allylic alcohols in combination with tert-butyl hydroperoxide (TBHP). It also exhibits insulin mimetic properties, in that in can stimulate the phosphorylation of protein kinase B (PKB/Akt) and glycogen synthase kinase-3 (GSK3), as well as inhibit tyrosine phosphatase (PTPase). This gives it anti-diabetic properties. Vanadium is a transition metal with the chemical symbol V and atomic number 23. The element usually combines with other elements such as oxygen, sodium, sulfur, or chloride, and occurs naturally in about 65 different minerals and in fossil fuel deposits. Vanadium is found in many organisms, and is used by some life forms as an active center of enzymes. (L837, L838, L851) 3153-26-2 5486770 C10H18O5V 265.028090 Blue/green solid. Oral (L837) ; inhalation (L837) ; dermal (L837) Vanadium damages alveolar macrophages by decreasing the macrophage membrane integrity, thus impairing the cells' phagocytotic ability and viability. The pentavalent form of vanadium, vanadate, is a potent inhibitor of the Ca+-ATPase and Na+,K+-ATPase of plasma membranes, which decreases intracellular ATP concentration. Vanadium is also believed to induce the production of reactive oxygen species. This may damage DNA and also cause oxidative stress, which can damage the reproductive system. Vanadium also inhibits protein tyrosine phosphatases, producing insulin-like effects. (L837, A247, A248, A249, A250, A251) Vanadium is absorbed mainly via inhalation, though small amounts can be absorbed through the skin and gastrointestional tract. It is rapidly distributed in the plasma, mainly to the kidney, liver, lungs, heart, bone, where it tends to accumulate. With the help of cytochrome P-450 enzymes, it can interconvert between its two oxidation states, vanadyl (V+4) and vanadate (V+5). Both states of vanadium can reversibly bind to transferrin protein in the blood and then be taken up into erythrocytes. Vanadium is excreted mainly in the urine. (L837) No indication of carcinogenicity to humans (not listed by IARC). Vanadyl acetylacetonate is used in organic chemistry as a reagent in the epoxidation of allylic alcohols in combination with tert-butyl hydroperoxide (TBHP). It also exhibits insulin mimetic properties, in that in can stimulate the phosphorylation of protein kinase B (PKB/Akt) and glycogen synthase kinase-3 (GSK3), as well as inhibit tyrosine phosphatase (PTPase). This gives it anti-diabetic properties. (L851) Acute Inhalation: 0.0002 mg/m3 (L134) Intermediate Oral: 0.003 mg/kg/day (L134) Breathing high levels of vanadium affects the lungs, throat, and eyes. Ingestion of vanadium may cause kidney and liver damage, birth defects, or death. (L837) Inhalation of vanadium causes lung irritation, coughing, wheezing, chest pain, runny nose, and a sore throat. (L837) 2009-06-19T21:59:04Z 2026-04-06T12:03:19Z CPD-4521 C054082 Vanadyl acetylacetonate true O.[V+4].[H]\C(C(C)[O-])=C(/C)[O-].[H]\C(C(C)[O-])=C(/C)[O-] C10H18O5V InChI=1S/2C5H9O2.H2O.V/c2*1-4(6)3-5(2)7;;/h2*3-4,7H,1-2H3;1H2;/q2*-1;;+4/p-2/b2*5-3-;; NXJSXZSKDPQXKX-XQGOTRMOSA-L 269.191 269.059381 Exogenous Solid CHEM001404 NS00122803 vanadium(4+) ion bis((2Z)-pent-2-ene-2,4-bis(olate)) hydrate