Metabolite Card

Formula: C18H34O2 (282.2559)
SMILES: CCCCCCCC\C=C/CCCCCCCC(O)=O

Synonyms [en]

oleic acid; oleate; (9Z)-Octadecenoic acid; cis-9-Octadecenoic acid; cis-Oleic acid; (Z)-Octadec-9-enoic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(9Z)-Octadecenoic acid. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000000726). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70%). Oleic acid triglycerides also make up 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 112-80-1
  • CAS Registry Number: 2027-47-6
  • CAS Registry Number: 9000-69-5
  • CAS Registry Number: 99148-48-8
  • PubChem: 3978
  • PubChem: 445639
  • PubChem: 965
  • ChEBI: ChEBI:16196
  • HMDB: HMDB0000207
  • HMDB: HMDB00207
  • LipidMaps: LMFA01030002
  • KEGG: C00712
  • NCBI MeSH: Oleic Acid
  • Wikipedia: Oleic_acid
  • DrugBank: DB04224
  • RefMet: RM0151650
  • MoNA: BAF_UVA_POS001490
  • MoNA: CA000168
  • MoNA: CCMSLIB00005720587
  • MoNA: FiehnHILIC001410
  • MoNA: FiehnHILIC002892
  • MoNA: FiehnLib000702
  • MoNA: HMDB0000207_c_ms_1874
  • MoNA: HMDB0000207_ms_ms_285572
  • MoNA: HMDB0000207_ms_ms_285573
  • MoNA: HMDB0000207_ms_ms_285574
  • MoNA: HMDB0000207_ms_ms_285575
  • MoNA: HMDB0000207_ms_ms_334
  • MoNA: HMDB0000207_ms_ms_335
  • MoNA: HMDB0000207_ms_ms_336
  • MoNA: HMDB0000207_ms_ms_797
  • MoNA: HMDB0000207_ms_ms_798
  • MoNA: HMDB0000207_ms_ms_799
  • MoNA: JP003087
  • MoNA: LipidBlast2022_953883
  • MoNA: LipidBlast417794
  • MoNA: MetaboBASE0989
  • MoNA: MetaboBASE0990
  • MoNA: MetaboBASE0991
  • MoNA: MetaboBASE0992
  • MoNA: MetaboBASE0993
  • MoNA: MoNA032557
  • MoNA: MoNA032558
  • MoNA: MoNA032559
  • MoNA: MoNA037349
  • MoNA: MT000029
  • MoNA: PR010209
  • MoNA: PS031501
  • MoNA: PS031502
  • MoNA: RP029011
  • MoNA: RP029012
  • Metlin: METLIN_190
  • Metlin: METLIN_45774

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02813 4.2.1.53 (R)-10-hydroxystearate 10-hydro-lyase
KEGG:R02814 3.1.2.14 oleoyl-[acyl-carrier-protein] hydrolase
KEGG:R08176 3.1.2.2 oleoyl-CoA hydrolase
KEGG:R09452 1.14.14.80 (9Z)-octadecenoic acid,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (omega-hydroxylating)
KEGG:R09462 1.11.2.3 oleate:lipid-hydroperoxide oxidoreductase (9,10-epoxidising)
KEGG:R09537 3.5.1.99 fatty acylamide amidohydrolase
KEGG:R10576 1.13.11.77 oleate:oxygen (10S)-oxidoreductase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
Plant Reactome:R-OSA-2744345 Metabolism and regulation
Plant Reactome:R-OSA-2744344 Secondary metabolism
Plant Reactome:R-OSA-1119418 Suberin biosynthesis
WikiPathways:WP4491 Elongation of (very) long chain fatty acids
WikiPathways:WP4724 Omega-9 fatty acid synthesis
WikiPathways:WP5241 Mitochondrial beta-oxidation
WikiPathways:WP1307 Fatty acid beta-oxidation
WikiPathways:WP5181 Roles of ceramides in development of insulin resistance
WikiPathways:WP419 Mitochondrial LC-Fatty Acid Beta-Oxidation
WikiPathways:WP4351 Omega-9 fatty acid synthesis
WikiPathways:WP4853 Linoleic acid metabolism affected by SARS-CoV-2
WikiPathways:WP4346 Cholesterol metabolism with Bloch and Kandutsch-Russell pathways
WikiPathways:WP5324 Octadecanoid formation from linoleic acid
PathBank:SMP0012493 Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:0)
PathBank:SMP0012497 Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0012501 Triacylglycerol Degradation TG(16:0/18:1(9Z)/20:1(13Z))
PathBank:SMP0012637 Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:0)
PathBank:SMP0012641 Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0012645 Triacylglycerol Degradation TG(18:0/18:1(9Z)/20:1(13Z))
PathBank:SMP0012757 Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:0)
View All Pathways