ContaminantDB: Vanadyl acetylacetonate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (47)XML

Record Information

Version

1.0

Creation Date

2009-06-19 21:59:04 UTC

Update Date

2026-04-06 12:03:19 UTC

Accession Number

CHEM001404

Identification

Common Name

Vanadyl acetylacetonate

Class

Small Molecule

Description

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. (7, 8, 9)

Contaminant Sources

T3DB toxins

Contaminant Type

Industrial/Workplace Toxin
Organic Compound
Organometallic
Synthetic Compound
Vanadium Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vanadium(4+) ion bis((2Z)-pent-2-ene-2,4-bis(olic acid)) hydric acid	Generator

Chemical Formula

C₁₀H₁₈O₅V

Average Molecular Mass

269.191 g/mol

Monoisotopic Mass

269.059 g/mol

CAS Registry Number

3153-26-2

IUPAC Name

vanadium(4+) ion bis((2Z)-pent-2-ene-2,4-bis(olate)) hydrate

Traditional Name

vanadium(4+) ion bis((2Z)-pent-2-ene-2,4-bis(olate)) hydrate

SMILES

O.[V+4].[H]\C(C(C)[O-])=C(/C)[O-].[H]\C(C(C)[O-])=C(/C)[O-]

InChI Identifier

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-;;

InChI Key

NXJSXZSKDPQXKX-XQGOTRMOSA-L

Chemical Taxonomy

Description

belongs to the class of organic compounds known as enolates. These are deprotonated anions of enols. They have diverse forms with either of the general structure [R1]C([R2])=C([R3])[O-], RC([CH2-])=O, or R1C(R1)=COM (M=metal).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Enolates

Direct Parent

Enolates

Alternative Parents

Substituents

Organic transition metal salt
Enolate
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Alkoxide
Aliphatic acyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Blue/green solid.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.93 g/L	ALOGPS
logP	3.25	ALOGPS
logP	0.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.74 m³·mol⁻¹	ChemAxon
Polarizability	10.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Toxicity Profile

Route of Exposure

Oral (7) ; inhalation (7) ; dermal (7)

Mechanism of Toxicity

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. (7, 1, 2, 3, 4, 5)

Metabolism

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. (7)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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. (9)

Minimum Risk Level

Acute Inhalation: 0.0002 mg/m3 (6) Intermediate Oral: 0.003 mg/kg/day (6)

Health Effects

Breathing high levels of vanadium affects the lungs, throat, and eyes. Ingestion of vanadium may cause kidney and liver damage, birth defects, or death. (7)

Symptoms

Inhalation of vanadium causes lung irritation, coughing, wheezing, chest pain, runny nose, and a sore throat. (7)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Vanadyl acetylacetonate (CHEM001404)

Structure for CHEM001404: Vanadyl acetylacetonate