Erucic acid (BioCAD00000010675)

blood feces adrenal gland placenta plant natural products microbial natural products

Metabolite Card

Formula: C22H42O2 (338.3185)
SMILES: CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O

Synonyms [en]

erucic acid; cis-13-Docosenoic acid; (13Z)-Docosenoic acid; C22:1n-9; trans-brassidic acid; 13-cis-Docosenoic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Erucic 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: BioCAD00000010675). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Erucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Erucic acid’s ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:Ln9) and erucic acid (22:1N9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. Human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2% erucic acid by weight in the US and 5% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. napus and B. rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1072-39-5
  • CAS Registry Number: 112-86-7
  • CAS Registry Number: 506-33-2
  • PubChem: 5281116
  • PubChem: 5282772
  • ChEBI: ChEBI:165494
  • ChEBI: ChEBI:28792
  • HMDB: HMDB0002068
  • LipidMaps: LMFA01030089
  • LipidMaps: LMFA01030090
  • KEGG: C08316
  • BioCyc: CPD-14292
  • NCBI MeSH: erucic acid
  • Wikipedia: Erucic_acid
  • RefMet: RM0153624
  • RefMet: RM0153625
  • MoNA: EMBL-MCF_spec347848
  • MoNA: HMDB0002068_c_ms_2040
  • MoNA: HMDB0002068_ms_ms_1978
  • MoNA: HMDB0002068_ms_ms_1979
  • MoNA: HMDB0002068_ms_ms_1980
  • MoNA: LipidBlast2022_953901
  • MoNA: LipidBlast417819
  • MoNA: MoNA016628
  • Metlin: METLIN_34769
  • Metlin: METLIN_3555
  • Coconut NaturalProduct: CNP0242452.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R08187 3.1.2.- C16531 + C00001<=>C00010 + C08316
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Organism Source

Taxonomy Source

  1. Achyranthes aspera [ncbi taxid: 240005]
  2. Aloe africana [ncbi taxid: 1080010]
  3. Aloe ferox [ncbi taxid: 117798]
  4. Aloe spicata [ncbi taxid: 992642]
  5. Aloe vera [ncbi taxid: 34199]
  6. Anarhichas lupus [ncbi taxid: 8204]
  7. Anthopleura elegantissima [ncbi taxid: 6110]
  8. Belone belone [ncbi taxid: 129037]
  9. Brassica campestris [ncbi taxid: ]
  10. Brassica napus [ncbi taxid: 3708]
  11. Brassica napus var. napus [ncbi taxid: 138011]
  12. Calophyllum calaba [ncbi taxid: 883767]
  13. Calophyllum inophyllum [ncbi taxid: 158927]
  14. Camelina sativa [ncbi taxid: 90675]
  15. Cheiranthus cheiri [ncbi taxid: ]
  16. Citrullus lanatus [ncbi taxid: 3654]
  17. Cynomorium songaricum [ncbi taxid: 627609]
  18. Dioscorea species [ncbi taxid: ]
  19. Fagopyrum esculentum [ncbi taxid: 3617]
  20. Ficus carica [ncbi taxid: 3494]
  21. Glycine max [ncbi taxid: 3847]
  22. Grevillea robusta [ncbi taxid: 105748]
  23. Homo sapiens [ncbi taxid: 9606]
  24. Lepidium sativum [ncbi taxid: 33125]
  25. Linum usitatissimum [ncbi taxid: 4006]
  26. Lupinus albus [ncbi taxid: 3870]
  27. Luzuriaga parviflora [ncbi taxid: 140587]
  28. Microstomus kitt [ncbi taxid: 106175]
  29. Morus alba var. multicaulis [ncbi taxid: 170012]
  30. Nelumbo nucifera [ncbi taxid: 4432]
  31. Nephrops norvegicus [ncbi taxid: 6829]
  32. Ocotea suaveolens [ncbi taxid: ]
  33. Pachyrhizus erosus [ncbi taxid: 109171]
  34. Paeonia lactiflora [ncbi taxid: 35924]
  35. Patrinia scabiosifolia [ncbi taxid: 300888]
  36. Patrinia villosa [ncbi taxid: 183944]
  37. Pittosporum crassifolium [ncbi taxid: 317701]
  38. Pringlea antiscorbutica [ncbi taxid: 203624]
  39. Psophocarpus tetragonolobus [ncbi taxid: 3891]
  40. Raphanus sativus [ncbi taxid: 3726]
  41. Reinhardtius hippoglossoides [ncbi taxid: 111784]
  42. Salmonella enterica subsp. enterica serovar anatum [ncbi taxid: 58712]
  43. Sebastes alutus [ncbi taxid: 72055]
  44. Shorea resina-nigra [ncbi taxid: ]
  45. Sinapis alba [ncbi taxid: 3728]
  46. Streptomyces griseoincarnatus strain HK12 [ncbi taxid: ]
  47. Struthiopteris amabilis [ncbi taxid: 120687]
  48. Terminalia chebula [ncbi taxid: 155022]
  49. Trachycarpus fortunei [ncbi taxid: 14027]
  50. Tropaeolum majus [ncbi taxid: 4020]
  51. Vigna unguiculata [ncbi taxid: 3917]
  52. Vitis vinifera [ncbi taxid: 29760]
  53. Xanthoparmelia camtschadalis [ncbi taxid: 983630]

Pathway Synthetic

pathway id name
WikiPathways:WP4491 Elongation of (very) long chain fatty acids
PathBank:SMP0012601 Triacylglycerol Degradation TG(16:0/22:1(13Z)/18:0)
PathBank:SMP0012605 Triacylglycerol Degradation TG(16:0/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0012609 Triacylglycerol Degradation TG(16:0/22:1(13Z)/20:1(13Z))
PathBank:SMP0012745 Triacylglycerol Degradation TG(18:0/22:1(13Z)/18:0)
PathBank:SMP0012749 Triacylglycerol Degradation TG(18:0/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0012753 Triacylglycerol Degradation TG(18:0/22:1(13Z)/20:1(13Z))
PathBank:SMP0012889 Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:0)
PathBank:SMP0012893 Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0012897 Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/20:1(13Z))
PathBank:SMP0013033 Triacylglycerol Degradation TG(18:1(11Z)/22:1(13Z)/18:0)
PathBank:SMP0013037 Triacylglycerol Degradation TG(18:1(11Z)/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0013041 Triacylglycerol Degradation TG(18:1(11Z)/22:1(13Z)/20:1(13Z))
PathBank:SMP0013177 Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:1(13Z)/18:0)
PathBank:SMP0013181 Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0013185 Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:1(13Z)/20:1(13Z))
PathBank:SMP0013321 Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:0)
PathBank:SMP0013325 Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:3(6Z,9Z,12Z))
PathBank:SMP0013329 Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:1(13Z))
PathBank:SMP0013377 Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(11Z)/22:1(13Z))
View All Pathways