13-Docosenoic acid
PubChem CID: 8216
Connections displayed (default: 10).
Loading graph...
| Compound Synonyms | docos-13-enoic acid, 13-Docosenoic acid, 1072-39-5, Erucic acid 98%, DTXSID30859200, AKOS028108914, CH3(CH2)7CH=CH(CH2)11COOH, NCI60_029063, XE181289 |
|---|---|
| Topological Polar Surface Area | 37.3 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 24.0 |
| Description | Before genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil from rapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would get stripped out of the genome as well, greatly reducing its valuable erucic acid content. Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability. Later trials showed that rats had the same problems with other vegetable fatty acids, because rats are poor at metabolising some fats. The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that of its competitors., Erucic acid is a 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. Its 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., Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ?-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50% of their oils. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid., The name erucic means: of or pertaining to eruca, which is a genus of flowering plants in the family Brassicaceae. It is also the Latin for coleworth, which today is better known as kale. Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. It is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. For industrial purposes, a High-Erucic Acid Rapeseed (HEAR) has been developed. These cultivars can yield 40% to 60% of the total oil recovered as erucic acid. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 284.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | docos-13-enoic acid |
| Prediction Hob | 0.0 |
| Class | Fatty Acyls |
| Xlogp | 8.7 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Fatty acids and conjugates |
| Molecular Formula | C22H42O2 |
| Prediction Swissadme | 0.0 |
| Inchi Key | DPUOLQHDNGRHBS-UHFFFAOYSA-N |
| Fcsp3 | 0.8636363636363636 |
| Logs | -4.123 |
| Rotatable Bond Count | 19.0 |
| State | Solid |
| Logd | 2.213 |
| Synonyms | (13Z)-13-Docosenoate, (13Z)-13-Docosenoic acid, (13Z)-Docosenoate, (13Z)-Docosenoic acid, (Z)-13-Docosenoate, (Z)-13-Docosenoic acid, (Z)-Docos-13-enoate, (Z)-Docos-13-enoic acid, «, delta», 13-cis-Docosenoic acid, 13-cis-Docosenoate, 13-cis-Docosenoic acid, 13-docosenoate, 13-Docosenoic acid, 13-Docosenoic acid (acd/name 4.0), 13-Docosenoic acid, (Z)-, 22:1Omega9, Brassidic acid, C22:1N-9, cis -13-Docosenoic acid, cis-13-Docosenoate, cis-13-Docosenoic acid, cis-delta(13)-Docosenoate, cis-Delta(13)-Docosenoic acid, cis-Eruate, cis-Erucic acid, cis-Eruic acid, cis-δ(13)-docosenoate, cis-δ(13)-docosenoic acid, delta 13-cis-Docosenoate, delta 13-cis-Docosenoic acid, delta.13-cis-Docosenoate, delta.13-cis-Docosenoic acid, Docos-13c-enoate, Docos-13c-enoic acid, Erucasaeure, Erucate, Erucic acid, pract, Prifrac 2990, trans -13-Docosenoic acid, Erucic acid, (e)-isomer, Erucic acid, (Z)-isomer, Erucic acid, potassium salt, (Z)-isomer, Erucic acid, sodium salt, (Z)-isomer |
| Substituent Name | Very long-chain fatty acid, Unsaturated fatty acid, Straight chain fatty acid, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aliphatic acyclic compound |
| Compound Name | 13-Docosenoic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 338.318 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 338.318 |
| Hydrogen Bond Acceptor Count | 2.0 |
| Molecular Weight | 338.6 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 1.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Esol | -6.865471200000002 |
| Inchi | InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24) |
| Smiles | CCCCCCCCC=CCCCCCCCCCCCC(=O)O |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Very long-chain fatty acids |
- 1. Outgoing r'ship
FOUND_INto/from Borago Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Brassica Napus (Plant) Rel Props:Source_db:cmaup_ingredients - 3. Outgoing r'ship
FOUND_INto/from Camellia Sinensis (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Cynomorium Songaricum (Plant) Rel Props:Source_db:cmaup_ingredients - 5. Outgoing r'ship
FOUND_INto/from Eruca Sativa (Plant) Rel Props:Source_db:fooddb_chem_all - 6. Outgoing r'ship
FOUND_INto/from Ficus Carica (Plant) Rel Props:Source_db:cmaup_ingredients - 7. Outgoing r'ship
FOUND_INto/from Glycine Max (Plant) Rel Props:Source_db:fooddb_chem_all - 8. Outgoing r'ship
FOUND_INto/from Lepidium Sativum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 9. Outgoing r'ship
FOUND_INto/from Linum Usitatissimum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 10. Outgoing r'ship
FOUND_INto/from Lupinus Albus (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 11. Outgoing r'ship
FOUND_INto/from Nasturtium Officinale (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Nelumbo Nucifera (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 13. Outgoing r'ship
FOUND_INto/from Oenothera Biennis (Plant) Rel Props:Source_db:fooddb_chem_all - 14. Outgoing r'ship
FOUND_INto/from Psophocarpus Tetragonolobus (Plant) Rel Props:Source_db:fooddb_chem_all - 15. Outgoing r'ship
FOUND_INto/from Raphanus Sativus (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 16. Outgoing r'ship
FOUND_INto/from Sinapis Alba (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 17. Outgoing r'ship
FOUND_INto/from Terminalia Chebula (Plant) Rel Props:Source_db:cmaup_ingredients - 18. Outgoing r'ship
FOUND_INto/from Vigna Unguiculata (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all - 19. Outgoing r'ship
FOUND_INto/from Vitis Vinifera (Plant) Rel Props:Source_db:fooddb_chem_all