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Record Information
Version2.0
Creation Date2009-06-19 21:58:49 UTC
Update Date2014-12-24 20:23:57 UTC
Accession NumberT3D1462
Identification
Common NameZinc oleate
ClassSmall Molecule
DescriptionZinc oleate is a chemical compound of zinc. Zinc is a metallic element with the atomic number 30. It is found in nature most often as the mineral sphalerite. Though excess zinc in harmful, in smaller amounts it is an essential element for life, as it is a cofactor for over 300 enzymes and is found in just as many transcription factors. (2, 3)
Compound Type
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
  • Zinc Compound
Chemical Structure
Thumb
Synonyms
Synonym
9-Octadecenoic acid (9Z)-, zinc salt
9-Octadecenoic acid (Z), zinc salt
9-Octadecenoic acid (Z), zinc salt (9ci)
Oleic acid, zinc salt
Zinc dioleate
Zinc oleate (1:2)
Zinc oleic acid
Chemical FormulaC35H64O4Zn2
Average Molecular Mass679.698 g/mol
Monoisotopic Mass676.339 g/mol
CAS Registry Number557-07-3
IUPAC Name{[(9Z)-12-(pentylzincio)dodec-9-enoyl]oxy}zincio (9Z)-octadec-9-enoate
Traditional Name{[(9Z)-12-(pentylzincio)dodec-9-enoyl]oxy}zincio (9Z)-octadec-9-enoate
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)O[Zn]OC(=O)CCCCCCC\C=C/CC[Zn]CCCCC
InChI IdentifierInChI=1S/C18H34O2.C12H21O2.C5H11.2Zn/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;1-2-3-4-5-6-7-8-9-10-11-12(13)14;1-3-5-4-2;;/h9-10H,2-8,11-17H2,1H3,(H,19,20);3-4H,1-2,5-11H2,(H,13,14);1,3-5H2,2H3;;/q;;;;+2/p-2/b10-9-;4-3-;;;
InChI KeyInChIKey=HKLJKICSWLCBJC-CEKJYYKZSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid salt
  • Dialkylzinc
  • Organic metal salt
  • Organic transition metal salt
  • Organic oxygen compound
  • Organozinc compound
  • Transition metal alkyl
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organometallic compound
  • Organic transition metal moeity
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.1e-06 g/LALOGPS
logP10.3ALOGPS
logP10.53ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity168.68 m³·mol⁻¹ChemAxon
Polarizability76.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0096006000-a0a2e348da5d9edee6d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1095012000-fc1838c5dc4c6b2d2b8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9270001000-0ab144d2597a1d7a63a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-1903007000-eb0163a4819db30b6ce0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03du-2498122000-9a3fafa07dae27b99391JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2793010000-bbab41da7c9d79c58fa6JSpectraViewer
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityAnaemia results from the excessive absorption of zinc suppressing copper and iron absorption, most likely through competitive binding of intestinal mucosal cells. Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS). Stomach acid dissolves metallic zinc to give corrosive zinc chloride, which can cause damage to the stomach lining. Metal fume fever is thought to be an immune response to inhaled zinc. (2, 3, 1)
MetabolismZinc can enter the body through the lungs, skin, and gastrointestinal tract. Intestinal absorption of zinc is controlled by zinc carrier protein CRIP. Zinc also binds to metallothioneins, which help prevent absorption of excess zinc. Zinc is widely distributed and found in all tissues and tissues fluids, concentrating in the liver, gastrointestinal tract, kidney, skin, lung, brain, heart, and pancreas. In the bloodstream zinc is found bound to carbonic anhydrase in erythrocytes, as well as bound to albumin, _2-macroglobulin, and amino acids in the the plasma. Albumin and amino acid bound zinc can diffuse across tissue membranes. Zinc is excreted in the urine and faeces. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelIntermediate Oral: 0.3 mg/kg/day (5) Chronic Oral: 0.3 mg/kg/day (5)
Health EffectsChronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (3)
SymptomsIngestion of large doses of zinc causes stomach cramps, nausea, and vomiting. Acute inhalation of large amounts of zinc causes metal fume fever, which is characterized by chills, fever, headache, weakness, dryness of the nose and throat, chest pain, and coughing. Dermal contact with zinc results in skin irritation. (3)
TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6436086
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDZinc oleate
PDB IDNot Available
ACToR ID18499
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1462.pdf
General References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]
  2. Wikipedia. Zinc. Last Updated 24 March 2009. [Link]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for zinc. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Metallothionein. Last Updated 20 December 2008. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name:
SOD1
Uniprot ID:
P00441
Molecular Weight:
15935.685 Da
References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]