(9Z)-Octadecenoic acid (BioCAD00000000726)
blood cerebrospinal fluid (csf) feces saliva urine adipose tissue epidermis intestine liver pancreas placenta prostate skeletal muscle
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
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.
DBLinks
- CAS Registry Number: 112-80-1
- PubChem CID: 445639
- ChEBI: 16196
- HMDB: HMDB0000207
- LipidMaps: LMFA01030002
- KEGG: C00712
- BioCyc:
- NCBI MeSH: Oleic Acid
- Wikipedia: Oleic_acid
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
- WishartLab ClassyFire: [Fatty acids and conjugates] Fatty acids and conjugates
- RefMet: [Unsaturated FA] Unsaturated FA
- LipidMaps: [Unsaturated fatty acids [FA0103]] Unsaturated fatty acids [FA0103]
- ChEBI: [CHEBI:16196] oleic acid
| 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 |
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) |