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Showing Compound Oleic acid (FDB012858)

Record Information
Version1.0
Creation date2010-04-08 22:10:24 UTC
Update date2019-11-26 03:07:45 UTC
Primary IDFDB012858
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOleic acid
DescriptionMajor constituent of plant oils e.g. olive oil (ca. 80%), almond oil (ca. 80%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. The trans isomer of oleic acid is called elaidic acid.
CAS Number112-80-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(9Z)-Octadecenoic acidChEBI
(Z)-Octadec-9-enoic acidChEBI
18:1 N-9ChEBI
18:1DElta9cisChEBI
C18:1 N-9ChEBI
cis-9-Octadecenoic acidChEBI
cis-Delta(9)-Octadecenoic acidChEBI
cis-Oleic acidChEBI
FA 18:1ChEBI
Octadec-9-enoic acidChEBI
OelsaeureChEBI
OleateChEBI
(9Z)-OctadecenoateGenerator
(Z)-Octadec-9-enoateGenerator
cis-9-OctadecenoateGenerator
cis-delta(9)-OctadecenoateGenerator
cis-Δ(9)-octadecenoateGenerator
cis-Δ(9)-octadecenoic acidGenerator
cis-OleateGenerator
Octadec-9-enoateGenerator
cis 9 Octadecenoic acidMeSH
9 Octadecenoic acidMeSH
9-Octadecenoic acidMeSH
(9Z)-9-OctadecenoateHMDB
(9Z)-9-Octadecenoic acidHMDB
(Z)-9-OctadecanoateHMDB
(Z)-9-Octadecanoic acidHMDB
9,10-OctadecenoateHMDB
9,10-Octadecenoic acidHMDB
9-(Z)-OctadecenoateHMDB
9-(Z)-Octadecenoic acidHMDB
9-OctadecenoateHMDB
Century CD fatty acidHMDB
cis-Octadec-9-enoateHMDB
cis-Octadec-9-enoic acidHMDB
DistolineHMDB
Emersol 210HMDB
Emersol 211HMDB
Emersol 213HMDB
Emersol 220 white oleateHMDB
Emersol 220 white oleic acidHMDB
Emersol 221 low titer white oleateHMDB
Emersol 221 low titer white oleic acidHMDB
Emersol 233LLHMDB
Emersol 6321HMDB
Emersol 6333 NFHMDB
Emersol 7021HMDB
Glycon roHMDB
Glycon woHMDB
groco 2HMDB
groco 4HMDB
groco 5lHMDB
groco 6HMDB
Industrene 104HMDB
Industrene 105HMDB
Industrene 205HMDB
Industrene 206HMDB
L'acide oleiqueHMDB
MetauponHMDB
OelsauereHMDB
Oleic acid extra pureHMDB
OleinateHMDB
Oleinic acidHMDB
PamolynHMDB
Pamolyn 100HMDB
Pamolyn 100 FGHMDB
Pamolyn 100 FGKHMDB
Pamolyn 125HMDB
Priolene 6900HMDB
Red oilHMDB
tego-Oleic 130HMDB
Vopcolene 27HMDB
Wecoline ooHMDB
Z-9-OctadecenoateHMDB
Z-9-Octadecenoic acidHMDB
Acid, 9-octadecenoicMeSH, HMDB
Acid, oleicMeSH, HMDB
Acid, cis-9-octadecenoicMeSH, HMDB
FA(18:1(9Z))HMDB
FA(18:1n9)HMDB
18:1Delta9cisChEBI
18:1δ9cisGenerator
9-(Z)-octadecenoatebiospider
9-(Z)-octadecenoic acidbiospider
9-Octadecenoic acid (Z)-biospider
9-Octadecenoic acid, (Z)-biospider
9-Octadecenoic acid, cis-biospider
Century cd fatty acidHMDB
Cis-oleatebiospider
Cis-oleic acidbiospider
cis-δ(9)-octadecenoateGenerator
cis-δ(9)-octadecenoic acidGenerator
Emersol 233llHMDB
FEMA 2815db_source
Glycon WOHMDB
Groco 2HMDB
Groco 4HMDB
Groco 5LHMDB
Groco 6HMDB
MYX 6121db_source
Pamolyn 100 fgHMDB
Pamolyn 100 fgkHMDB
Rapinic aciddb_source
Tego-oleic 130HMDB
Wecoline OOHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.68ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H34O2
IUPAC name(9Z)-octadec-9-enoic acid
InChI IdentifierInChI=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+
InChI KeyZQPPMHVWECSIRJ-MDZDMXLPSA-N
Isomeric SMILESCCCCCCCC\C=C\CCCCCCCC(O)=O
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 76.54%; H 12.13%; O 11.33%DFC
Melting PointMp 16° (stable form)DFC
Boiling PointBp5 203-205°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.9DFC
Refractive Indexn20D 1.4595DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b672018-05-25View Spectrum
GC-MSoleate, 1 TMS, GC-MS Spectrumsplash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSoleate, 1 TMS, GC-MS Spectrumsplash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-052f-9100000000-7618883a87bd14687fd5Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
Predicted GC-MSoleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bSpectrum
Predicted GC-MSoleate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401Spectrum
Predicted GC-MSoleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSoleate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-64594906d693e8a086502012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeed2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df502012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-001i-0090000000-89531b488fbe899c09e62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-92096c6b229762c5295f2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-5fe8495a19b387bf702c2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5d40399b1c736b4764452017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-45785aeb659bd8a092402017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0091000000-3946ac7663105c7c27002017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-ce1372cb3b5e841223492017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-92096c6b229762c5295f2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe0932272016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c545592016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b772016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07d2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID393217
ChEMBL IDCHEMBL8659
KEGG Compound IDC00712
Pubchem Compound ID445639
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00207
CRC / DFC (Dictionary of Food Compounds) IDBGT64-L:HMN62-J
EAFUS ID2802
Dr. Duke IDOLEIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001232
HET IDOLA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID112-80-1
GoodScent IDrw1029521
SuperScent IDNot Available
Wikipedia IDOleic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-alpha-reductase inhibitor50781 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing prostate size, promoting hair growth, and minimizing sebaceous gland activity.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Alpha-reductase inhibitor23924 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats conditions like benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing sebum production and slowing hair loss.DUKE
AnemiagenicAn agent that causes anemia, often by inducing hemolysis or inhibiting erythropoiesis. Therapeutically, understanding anemiagenic agents helps manage and prevent anemia in various medical conditions, such as hemolytic anemia and toxic exposures. Key medical uses include identifying and mitigating the effects of anemiagenic substances, like arsenic and certain medications.DUKE
Anti-alopecic52217 An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth.DUKE
Anti-androgenic35497 An agent that blocks the activity of male sex hormones (androgens), reducing their effects on the body. Therapeutically, it's used to treat conditions like prostate cancer, acne, and hirsutism, as well as manage symptoms of androgen-sensitive disorders, such as benign prostatic hyperplasia.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti leukotriene-D435222 An agent that blocks the action of leukotriene D4, reducing inflammation and bronchoconstriction. Therapeutically, it's used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting leukotriene-mediated responses, providing relief from symptoms such as wheezing, coughing, and shortness of breath.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
DermatitigenicAn agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments.DUKE
Name48318 flavorDUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
PercutaneostimulantA stimulant applied through the skin, enhancing biological responses and promoting therapeutic effects. Its key medical uses include pain management, wound healing, and muscle relaxation, making it a valuable treatment for various conditions, such as chronic pain and skin disorders.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Tyrosine kinase inhibitorAn agent that blocks the enzymatic activity of tyrosine kinases, enzymes responsible for the activation of many proteins involved in signal transduction pathways regulating cell growth and survival. Therapeutically, tyrosine kinase inhibitors are widely used in the treatment of various cancers and proliferative diseases, by halting aberrant signaling that drives tumor progression and pathological tissue remodeling.DUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Fatty-acid amide hydrolase 1FAAHO00519
Fatty-acid amide hydrolase 2FAAH2Q6GMR7
Fatty acid synthaseFASNP49327
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lard
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fried
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.