Docosadienoic acid

Docosadienoic acid
Names
	IUPAC name (13Z, 16Z)-docosa-13,16-dienoic acid
	Other names DDA
Identifiers
CAS Number	26764-24-9;
3D model (JSmol)	Interactive image;
ChemSpider	4471979;
KEGG	C16533;
PubChem CID	53741802;
UNII	4L3DC2UF5X;
	InChI InChI=1S/C22H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h18-21H,2-17H2,1H3,(H,23,24) Key: CVCXSNONTRFSEH-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCCCCCCCC=CC=CC(=O)O;
Properties
Chemical formula	C22H40O2
Molar mass	336.560 g·mol−1
Density	0.9 g/cm³
Solubility in water	insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Docosadienoic acid is a polyunsaturated very long-chain fatty acid (VLCFA) with a 22-carbon backbone and two double bonds.^[2]

Isomers

The acid exists in several isomeric forms,^[3] depending on the positions and configurations of the double bonds. These isomers play important roles in biological systems and are used in chemical synthesis.^[4]

Physical properties

Insoluble in water. Soluble in chloroform, hexane, ethanol.

Natural occurrence

Docosadienoic acid can be detected in modest concentrations, generally not exceeding 3%, in the seed oils of many plants, particularly Cruciferae and Ranunculaceae.^[5]

References

^ Tang, Yi-Xiong; Huang, Wei; Wang, Yu-Hui; Chen, Hong; Lu, Xiang-Yang; Tian, Yun; Ji, Xiao-Jun; Liu, Hu-Hu (1 August 2024). "Engineering Yarrowia lipolytica for sustainable Cis-13, 16-docosadienoic acid production". Bioresource Technology. 406: 130978. Bibcode:2024BiTec.40630978T. doi:10.1016/j.biortech.2024.130978. ISSN 0960-8524. PMID 38879057. Retrieved 12 June 2025.
^ McClance, R. (1998). Fatty Acids: Seventh Supplement to the Fifth Edition of McCance and Widdowson's The Composition of Foods. Royal Society of Chemistry. p. 175. ISBN 978-0-85404-819-9. Retrieved 12 June 2025.
^ Blunt, John W.; Munro, Murray H. G. (19 September 2007). Dictionary of Marine Natural Products. CRC Press. ISBN 978-1-040-22179-2. Retrieved 12 June 2025.
^ Toldrá, Fidel; Nollet, Leo (8 March 2024). Handbook of Seafood and Seafood Products Analysis. CRC Press. p. 389. ISBN 978-1-003-82543-2. Retrieved 12 June 2025.
^ Azimova, Shakhnoza S.; Glushenkova, Anna I. (2012). Lipids, Lipophilic Components and Essential Oils from Plant Sources. Springer London. ISBN 978-0-85729-322-0. Retrieved 30 June 2025.

[1] Tang, Yi-Xiong; Huang, Wei; Wang, Yu-Hui; Chen, Hong; Lu, Xiang-Yang; Tian, Yun; Ji, Xiao-Jun; Liu, Hu-Hu (1 August 2024). "Engineering Yarrowia lipolytica for sustainable Cis-13, 16-docosadienoic acid production". Bioresource Technology. 406: 130978. Bibcode:2024BiTec.40630978T. doi:10.1016/j.biortech.2024.130978. ISSN 0960-8524. PMID 38879057. Retrieved 12 June 2025.

[2] McClance, R. (1998). Fatty Acids: Seventh Supplement to the Fifth Edition of McCance and Widdowson's The Composition of Foods. Royal Society of Chemistry. p. 175. ISBN 978-0-85404-819-9. Retrieved 12 June 2025.

[3] Blunt, John W.; Munro, Murray H. G. (19 September 2007). Dictionary of Marine Natural Products. CRC Press. ISBN 978-1-040-22179-2. Retrieved 12 June 2025.

[4] Toldrá, Fidel; Nollet, Leo (8 March 2024). Handbook of Seafood and Seafood Products Analysis. CRC Press. p. 389. ISBN 978-1-003-82543-2. Retrieved 12 June 2025.

[5] Azimova, Shakhnoza S.; Glushenkova, Anna I. (2012). Lipids, Lipophilic Components and Essential Oils from Plant Sources. Springer London. ISBN 978-0-85729-322-0. Retrieved 30 June 2025.

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