| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:26:42 UTC |
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| Update Date | 2020-06-04 22:58:57 UTC |
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| BMDB ID | BMDB0000207 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Oleic acid |
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| Description | Oleic acid, also known as pamolyn or oleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oleic acid exists in all living species, ranging from bacteria to humans. Oleic acid is a potentially toxic compound. Oleic acid has been found to be associated with several diseases known as colorectal cancer, schizophrenia, gestational diabetes, and lung cancer; also oleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (9Z)-Octadecenoic acid | ChEBI | | (Z)-Octadec-9-enoic acid | ChEBI | | 18:1 N-9 | ChEBI | | 18:1DElta9cis | ChEBI | | C18:1 N-9 | ChEBI | | cis-9-Octadecenoic acid | ChEBI | | cis-Delta(9)-Octadecenoic acid | ChEBI | | cis-Oleic acid | ChEBI | | FA 18:1 | ChEBI | | Octadec-9-enoic acid | ChEBI | | Oelsaeure | ChEBI | | Oleate | ChEBI | | (9Z)-Octadecenoate | Generator | | (Z)-Octadec-9-enoate | Generator | | cis-9-Octadecenoate | Generator | | cis-delta(9)-Octadecenoate | Generator | | cis-Δ(9)-octadecenoate | Generator | | cis-Δ(9)-octadecenoic acid | Generator | | cis-Oleate | Generator | | Octadec-9-enoate | Generator | | cis 9 Octadecenoic acid | MeSH | | 9 Octadecenoic acid | MeSH | | 9-Octadecenoic acid | MeSH | | (9Z)-9-Octadecenoate | HMDB | | (9Z)-9-Octadecenoic acid | HMDB | | (Z)-9-Octadecanoate | HMDB | | (Z)-9-Octadecanoic acid | HMDB | | 9,10-Octadecenoate | HMDB | | 9,10-Octadecenoic acid | HMDB | | 9-(Z)-Octadecenoate | HMDB | | 9-(Z)-Octadecenoic acid | HMDB | | 9-Octadecenoate | HMDB | | Century CD fatty acid | HMDB | | cis-Octadec-9-enoate | HMDB | | cis-Octadec-9-enoic acid | HMDB | | Distoline | HMDB | | Emersol 210 | HMDB | | Emersol 211 | HMDB | | Emersol 213 | HMDB | | Emersol 220 white oleate | HMDB | | Emersol 220 white oleic acid | HMDB | | Emersol 221 low titer white oleate | HMDB | | Emersol 221 low titer white oleic acid | HMDB | | Emersol 233LL | HMDB | | Emersol 6321 | HMDB | | Emersol 6333 NF | HMDB | | Emersol 7021 | HMDB | | Glycon ro | HMDB | | Glycon wo | HMDB | | groco 2 | HMDB | | groco 4 | HMDB | | groco 5l | HMDB | | groco 6 | HMDB | | Industrene 104 | HMDB | | Industrene 105 | HMDB | | Industrene 205 | HMDB | | Industrene 206 | HMDB | | L'acide oleique | HMDB | | Metaupon | HMDB | | Oelsauere | HMDB | | Oleic acid extra pure | HMDB | | Oleinate | HMDB | | Oleinic acid | HMDB | | Pamolyn | HMDB | | Pamolyn 100 | HMDB | | Pamolyn 100 FG | HMDB | | Pamolyn 100 FGK | HMDB | | Pamolyn 125 | HMDB | | Priolene 6900 | HMDB | | Red oil | HMDB | | tego-Oleic 130 | HMDB | | Vopcolene 27 | HMDB | | Wecoline oo | HMDB | | Z-9-Octadecenoate | HMDB | | Z-9-Octadecenoic acid | HMDB | | Acid, 9-octadecenoic | MeSH, HMDB | | Acid, oleic | MeSH, HMDB | | Acid, cis-9-octadecenoic | MeSH, HMDB | | FA(18:1(9Z)) | HMDB | | FA(18:1n9) | HMDB |
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| Chemical Formula | C18H34O2 |
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| Average Molecular Weight | 282.4614 |
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| Monoisotopic Molecular Weight | 282.255880332 |
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| IUPAC Name | (9Z)-octadec-9-enoic acid |
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| Traditional Name | oleic acid |
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| CAS Registry Number | 112-80-1 |
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| SMILES | CCCCCCCC\C=C/CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- |
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| InChI Key | ZQPPMHVWECSIRJ-KTKRTIGZSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Long-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Long-chain fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 13.4 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Adipose Tissue
- Blood
- Epidermis
- Intestine
- Liver
- Mammary Gland
- Milk
- Muscle
- Oocyte
- Pancreas
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Skeletal Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 74191.38 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 72947.31 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 710540.98 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 804930.87 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1047306.99 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1070050.28 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1242647.67 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1239461.39 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1289804.55 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1300531.68 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.1 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 21.1 +/- 0.4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 24 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 32 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 79.64 +/- 7.47 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 87.11 +/- 9.30 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 34.06 +/- 1.048 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.76 +/- 0.52 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 71.97 +/- 0.60 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 25384.0353 +/- 7080.624 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 23790.895 +/- 6584.980 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.1 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.1 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | details |
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| External Links |
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| HMDB ID | HMDB0000207 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012858 |
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| KNApSAcK ID | C00001232 |
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| Chemspider ID | 393217 |
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| KEGG Compound ID | C00712 |
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| BioCyc ID | OLEATE-CPD |
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| BiGG ID | Not Available |
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| Wikipedia Link | Oleic_acid |
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| METLIN ID | 190 |
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| PubChem Compound | 445639 |
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| PDB ID | Not Available |
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| ChEBI ID | 16196 |
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| References |
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| Synthesis Reference | Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
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