Obtusilic acid

Obtusilic acid

Names
IUPAC name (Z)-dec-4-enoic acid
Other names 4-Decenoic acid
Identifiers
CAS Number	505-90-8  N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32380
ChemSpider	4471776
ECHA InfoCard	100.007.295
EC Number	208-024-5
PubChem CID	5312351
UNII	6PR4L1KTAZ
CompTox Dashboard (EPA)	DTXSID001315543
InChI InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h6-7H,2-5,8-9H2,1H3,(H,11,12)/b7-6- Key: XKZKQTCECFWKBN-SREVYHEPSA-N
SMILES CCCCC/C=C\CCC(=O)O
Properties
Chemical formula	C10H18O2
Molar mass	170.252 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Obtusilic acid is a linear fatty acid composed of 10 carbon atoms, with one double bond ^[1] in the position 4=5 in cis-configuration. This is an Omega-6 acid of little nutritional interest with abbreviated notation 10:1 (n-6). ^{[2] [3]}

Discovery

The acid was initially isolated in the seed oil of Lindera obtusiloba , from which it takes its common name, in 1937 by the Japanese scientist Toyama and confirmed in the same year by Saburo Komori and Sei-ichi Ueno. ^{[4] [5]}

Natural occurrence

Lindera obtusiloba oil, Tohaku in Korean, which contains about 4% obtusilic acid, was an oil that Koreans applied to their hair. ^[6] Obtusilic acid has been isolated from only a few other plants of the family Lauraceae : Lindera praecox (≈5%), Litsea auriculata (≈4%), Lindera citriodora (≈3%).

Physical properties

At room temperature, the acid forms a liquid that boils at 148–150 °C at 13 mmHg. Between 4 °C and 20 °C, it has a density of 0.9197 g/cm³ and a refractive index of 1.4497 at 20 °C. The acid is soluble in benzene and diethyl ether.

Health effects

An increase in obtusilic acid in human blood and organs has been associated with acyl-CoA dehydrogenase deficiency. ^{[7] [8]}

References

1. Mikšík, I.; Tagliaro, F.; Tesarová, E.; Deyl, Z. (28 September 1998). Advanced Chromatographic and Electromigration Methods in BioSciences. Elsevier. p. 345. ISBN   978-0-08-085868-5 . Retrieved 15 April 2025.
2. Processing and Nutrition of Fats and Oils. John Wiley & Sons. 28 October 2013. p. 19. ISBN   978-0-8138-2767-4 . Retrieved 15 April 2025.
3. Wang, Zerong (26 May 2023). Amino Acids: Insights and Roles in Heterocyclic Chemistry: Volume 1: Protecting Groups. CRC Press. p. 9. ISBN   978-1-000-73887-2 . Retrieved 15 April 2025.
4. Coffey, S. (3 June 2016). Monocarbonyl Derivatives of Aliphatic Hydrocarbons, Their Analogues and Derivatives: A Modern Comprehensive Treatise. Elsevier. p. 239. ISBN   978-1-4832-2133-5 . Retrieved 15 April 2025.
5. Komori, Saburo; Ueno, Sei-ichi (1 September 1937). "Studies on the Unsaturated Lower Fatty Acids. On the Crystalline Derivatives of the Unsaturated Lower Fatty Acids". Bulletin of the Chemical Society of Japan . 12 (9): 433–435. doi:10.1246/bcsj.12.433. ISSN   0009-2673 . Retrieved 15 April 2025.
6. Furukawa, Kiyoshi; Nii, Hiromichi; Iwakiri, Mitsuo; Kubota, Takashi (1976). "The Fatty Acid Composition of the Seed Oil of Lindera obtusiloba Blume". Journal of Japan Oil Chemists' Society . 25 (4): 190–193. doi: 10.5650/jos1956.25.190 . Retrieved 15 April 2025.
7. Onkenhout, W.; Venizelos, V.; Scholte, H. R.; De Klerk, J. B.; Poorthuis, B. J. (June 2001). "Intermediates of unsaturated fatty acid oxidation are incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects". Journal of Inherited Metabolic Disease . 24 (3): 337–344. doi:10.1023/a:1010592232317. ISSN   0141-8955. PMID   11486898.
8. Heales, S. J. R.; Leonard, J. V. (31 July 1992). "Diagnosis of medium chain acyl CoA dehydrogenase deficiency by measurement of cis-4-decenoic acid in dried blood spots" . Clinica Chimica Acta . 209 (1): 61–66. doi:10.1016/0009-8981(92)90333-L. ISSN   0009-8981. PMID   1395039 . Retrieved 15 April 2025.