Stearidonic acid

Stearidonic acid
Names


Preferred IUPAC name (6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid
Identifiers
CAS Number	20290-75-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32389^Y
ChEMBL	ChEMBL484430^Y
ChemSpider	4471933^Y
ECHA InfoCard	100.127.224
PubChem CID	5312508
UNII	P4CEK3495O^Y
CompTox Dashboard (EPA)	DTXSID20920493
InChI InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-^Y Key: JIWBIWFOSCKQMA-LTKCOYKYSA-N^Y InChI=1/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12- Key: JIWBIWFOSCKQMA-LTKCOYKYBT
SMILES O=C(O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Chemical compound

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.

Stearidonic acid is a precursor to eicosapentaenoic acid.^[1]

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.^[2]

SDA is also a precursor to N-acylethanolamine (NAEs).^[3]^[4] Natural sources of this fatty acid are the seed oils of hemp, blackcurrant, corn gromwell,^[5] and Echium plantagineum, and the cyanobacterium Spirulina. SDA can also be synthesized in a lab. A GMO soybean source is approved by the European Food Safety Authority.^[6]

^ 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.
^ 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. doi:10.3389/fnut.2018.00012. PMC 5817065. PMID 29492405.
^ 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. PMC 4873519. PMID 27242881.
^ PubChem. "Stearidonic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-22.
^ "Corn Gromwell". NIAB. Archived from the original on 2011-07-04.
^ "Scientific Opinion on genetically modified soybean MON 87769". European Food Safety Authority. 2014-05-16. Retrieved 2019-02-18.