Stearidonic acid
Chemical compound
From Wikipedia, the free encyclopedia
Stearidonic acid (SDA: C18H28O2; 18:4, n-3) is an ω-3 fatty acid, sometimes called moroctic acid.
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| Names | |
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| Preferred IUPAC name
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.127.224 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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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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 human 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][failed verification][4]
Sources
Natural sources of this fatty acid are the seed oils of hemp (between 0.16 and 1.54% of the oil),[1] blackcurrant (between 2.5 and 4.5%),[5] Buglossoides arvensis (corn gromwell),[6] and Echium plantagineum, and the cyanobacterium Spirulina[citation needed].
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.[7] A GMO soybean source is approved by the European Food Safety Authority.[8]
SDA can also be synthesized in a lab.