ContaminantDB: Copper acetylacetonate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-06-19 21:58:29 UTC

Update Date

2026-04-06 12:55:17 UTC

Accession Number

CHEM001052

Identification

Common Name

Copper acetylacetonate

Class

Small Molecule

Description

Copper acetylacetonate is a chemical compound of copper. Copper is a chemical element with the symbol Cu and atomic number 29. Copper is an essential elements in plants and animals as it is required for the normal functioning of more than 30 enzymes. It occurs naturally throughout the environment in rocks, soil, water, and air. (4, 5)

Contaminant Sources

T3DB toxins

Contaminant Type

Copper Compound
Ester
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Organometallic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Copper acetylacetonic acid	Generator

Chemical Formula

C₁₀H₁₄CuO₄

Average Molecular Mass

261.762 g/mol

Monoisotopic Mass

261.019 g/mol

CAS Registry Number

13395-16-9

IUPAC Name

(3Z)-4-[({[(2E)-4-oxopent-2-en-2-yl]oxy}cuprio)oxy]pent-3-en-2-one

Traditional Name

(3Z)-4-[({[(2E)-4-oxopent-2-en-2-yl]oxy}cuprio)oxy]pent-3-en-2-one

SMILES

CC(=O)\C=C(\C)O[Cu]O\C(C)=C\C(C)=O

InChI Identifier

InChI=1S/2C5H8O2.Cu/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b4-3+;4-3-;

InChI Key

QYJPSWYYEKYVEJ-OHSCNOFNSA-L

Chemical Taxonomy

Description

belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Vinylogous acid
Enone
Acryloyl-group
Ketone
Organic transition metal salt
Enolate
Organic oxide
Hydrocarbon derivative
Organic copper salt
Organic salt
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 powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	2.9 g/L	ALOGPS
logP	1.08	ALOGPS
logP	-0.045	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	19.14	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	54.85 m³·mol⁻¹	ChemAxon
Polarizability	22.46 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

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-9070000000-2a7576c9aec3b22b3a55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9010000000-6f58a1929f2b55ad7e2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-9000000000-d0a9eac224962bbf5b44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1090000000-18b4ae5a638b2f7ca64b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fs-9080000000-70e92790e8aa1e980a28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-e721d1db9e05fb061122	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal (4)

Mechanism of Toxicity

Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia. Copper-induced emesis results from stimulation of the vagus nerve. (4, 9, 1, 7)

Metabolism

Copper is mainly absorbed through the gastrointestinal tract, but it can also be inhalated and absorbed dermally. It passes through the basolateral membrane, possibly via regulatory copper transporters, and is transported to the liver and kidney bound to serum albumin. The liver is the critical organ for copper homoeostasis. In the liver and other tissues, copper is stored bound to metallothionein, amino acids, and in association with copper-dependent enzymes, then partitioned for excretion through the bile or incorporation into intra- and extracellular proteins. The transport of copper to the peripheral tissues is accomplished through the plasma attached to serum albumin, ceruloplasmin or low-molecular-weight complexes. Copper may induce the production of metallothionein and ceruloplasmin. The membrane-bound copper transporting adenosine triphosphatase (Cu-ATPase) transports copper ions into and out of cells. Physiologically normal levels of copper in the body are held constant by alterations in the rate and amount of copper absorption, compartmental distribution, and excretion. (4, 6)

Toxicity Values

Not Available

Lethal Dose

10 to 20 grams for an adult human (copper salts). (8)

Carcinogenicity (IARC Classification)

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

Uses/Sources

Not Available

Minimum Risk Level

Acute Oral: 0.01 mg/kg/day (3) Intermediate Oral: 0.01 mg/kg/day (3)

Health Effects

People must absorb small amounts of copper every day because copper is essential for good health, however, high levels of copper can be harmful. Very-high doses of copper can cause damage to your liver and kidneys, and can even cause death. Copper may induce allergic responses in sensitive individuals. (5, 6)

Symptoms

Breathing high levels of copper can cause irritation of the nose and throat. Ingesting high levels of copper can cause nausea, vomiting, diarrhea, headache, dizziness, and respiratory difficulty. (5, 6)

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

Metal acetylacetonates

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

101642132

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

Copper acetylacetonate (CHEM001052)

Structure for CHEM001052: Copper acetylacetonate