Chemistry:Stearidonic acid
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| Preferred IUPAC name
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C18H28O2 | |
| Molar mass | 276.420 g·mol−1 |
| Density | 0.9334 g/cm3 (15 °C) |
| Melting point | 200 °C (392 °F; 473 K) decomposition |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Stearidonic acid (SDA: C18H28O2; 18:4, n-3) is an ω-3 fatty acid, sometimes called moroctic acid.
Biosynthesis
It is biosynthesized from alpha-linolenic acid (ALA: C18H30O2; 18:3, n-3) by the enzyme delta-6-desaturase, which removes two hydrogen (H) atoms.
Metabolism
Stearidonic acid is involved in the synthesis of longer-chain ω-3 fatty acids in animals (including humans), plants, and bacteria.[1] It is a precursor to eicosapentaenoic acid via a[2] eicosatetraenoic acid (20:4 ω-3) intermediate. Studies in humans volunteers and cell cultures suggest that SDA increases EPA levels more efficiently than an equimolar amount of ALA.[3]
SDA is also a precursor to N-acylethanolamine (NAEs).[1] [4]
Sources
Natural sources of this fatty acid are the seed oils of hemp,[1] blackcurrant, Buglossoides arvensis (corn gromwell),[5] and Echium plantagineum, and the cyanobacterium Spirulina.
As it is a precursor to other fatty acids, there has been efforts to enhance the content off stearidonic acid in various crops, such as soybeans.[6] A GMO soybean source is approved by the European Food Safety Authority.[7]
SDA can also be synthesized in a lab.
See also
- List of omega-3 fatty acids
- Omega-3 fatty acids
- Essential fatty acids
References
- ↑ 1.0 1.1 1.2 Galasso, Incoronata; Russo, Roberto; Mapelli, Sergio; Ponzoni, Elena; Brambilla, Ida M.; Battelli, Giovanna; Reggiani, Remo (2016-05-20). "Variability in Seed Traits in a Collection of Cannabis sativa L. Genotypes". Frontiers in Plant Science 7: 688. doi:10.3389/fpls.2016.00688. ISSN 1664-462X. PMID 27242881.
- ↑ Calder, Philip C. (2012). "Mechanisms of Action of (N-3) Fatty Acids". The Journal of Nutrition 142 (3): 592S–599S. doi:10.3945/jn.111.155259. PMID 22279140.
- ↑ Seidel, U; Eberhardt, K; Wiebel, M; Luersen, K; Ipharraguerre, IR; Haegele, FA; Winterhalter, P; Bosy-Westphal, A et al. (2024). "Stearidonic acid improves eicosapentaenoic acid status: studies in humans and cultured hepatocytes.". Frontiers in nutrition 11. doi:10.3389/fnut.2024.1359958. PMID 38974810.
- ↑ PubChem. "Stearidonic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/5312508.
- ↑ "Corn Gromwell". NIAB. http://www.niab.com/pages/id/319/Corn_Gromwell.
- ↑ Garg, Monika; Sharma, Natasha; Sharma, Saloni; Kapoor, Payal; Kumar, Aman; Chunduri, Venkatesh; Arora, Priya (2018). "Biofortified Crops Generated by Breeding, Agronomy, and Transgenic Approaches Are Improving Lives of Millions of People around the World". Frontiers in Nutrition 5: 12. doi:10.3389/fnut.2018.00012. PMID 29492405.
- ↑ "Scientific Opinion on genetically modified soybean MON 87769" (in en). 2014-05-16. http://www.efsa.europa.eu/en/efsajournal/pub/3644.
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