Oleic acid amide

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Structural formula
Structure of oleic acid amide
General
Surname Oleic acid amide
other names
  • cis -9,10-octadecenamide
  • ( Z ) -9,10-octadecenamide
  • OLEAMIDE ( INCI )
Molecular formula C 18 H 35 NO
Brief description

soft, fatty, slightly brownish substance

External identifiers / databases
CAS number 301-02-0
EC number 206-103-9
ECHA InfoCard 100.005.550
PubChem 5283387
Wikidata Q4370
properties
Molar mass 281.48 g mol −1
Physical state

firmly

Melting point

75-76 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-317-319-335
P: 261-280-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oleic acid amide is the carboxylic acid amide of oleic acid . It is formed in the body and is therefore one of the endogenous substances. There it is present as a cis isomer and is involved in a number of signaling processes. Industrial it becomes v. a. used in plastics production.

properties

Oleic acid amide is - like oleic acid or the related anandamide - a water-insoluble substance. It is a soft, fatty, slightly brownish substance. Technical oleic acid amide contains 20% saturated amides as secondary components and is obtained by heating ammonium oleate., Industrially, analogous to other fatty acid amides, by the reaction of oleic acid with ammonia.

Biological importance

Oleic acid amide was found in the cerebrospinal fluid of cats that were kept under sleep deprivation. It was initially referred to as "cerebrodia" because it was assumed to be a diene . A short time later it was finally identified as the “cis” isomer of oleic acid amide.

Oleic acid amide shows sleep-inducing effects and hypomotility . It interacts with potassium channels and with GABA A - and 5-HT 7 receptors . The interaction with the GABA A receptors seems to cause the sleep-inducing effect.

It could be shown that oleic acid amide interacts directly with the cannabinoid receptor 1 (CB 1 receptor). It also activates vanilloid TRPV1 receptors.

Whether it can be counted as an endocannabinoid, however, is still controversial despite the cannabinoid- like effects (increased appetite, hypothermia , hypoactivity).

Oleic acid amide is broken down by fatty acid amide hydrolase (FAAH).

Biochemical representation

The exact de novo synthesis pathway of oleic acid amide is not yet fully understood. It is believed, however, that oleic acid amide is formed from oleoyl- CoA and glycine . Here, glycine and oleoyl-CoA are said to condense enzymatically to oleoylglycine, which is catalyzed by the bile acid-CoA: amino acid N-acetyltransferase (BACAT) or a BACAT-like enzyme. Oleoylglycine can then be oxidatively converted to oleic acid amide by the enzyme PAM ( peptidylglycine-α-amidating monooxygenase ). Alternatively, oleic acid amide could be formed by direct reaction of oleoyl-CoA and ammonia, which is catalyzed by cytochrome c . A combination of the two pathways may also lead to oleic acid amide biosynthesis.

It is doubtful whether the fatty acid amide hydrolase (FAAH) can form oleic acid amide from oleic acid and ammonium (NH 4 + ) ( reverse reaction of the breakdown). On the other hand, very high concentrations of NH 4 + are required and the reaction has a pH optimum of more than 9. Physiologically, these conditions are very difficult to achieve.

Elaidic acid amide

trans isomer of oleic acid amide

Elaidic acid amide , the trans isomer of oleic acid amide, is biologically active, but much less than the cis isomer. Many of the effects observed with the cis isomer are also not detectable for the trans isomer.

Technical use

Oleic acid amide is used in plastics production. There it serves as a lubricant and, for example, makes it easier for plastic films to slide together. It is also a water repellent and can also be used as a raw material for cosmetics production. Finally, it is used as a slip agent in polyethylene and (in addition to erucic acid amide ) in polypropylene products.

It was recently shown that the oleic acid amide contained in polypropylene reaction vessels can also get into solution. This could then affect biochemical experiments.

literature

  • Hiley, CR. and Hoi, PM. (2007): Oleamide: a fatty acid amide signaling molecule in the cardiovascular system? In: Cardiovasc Drug Rev. 25 (1); 46-60; PMID 17445087 .

Individual evidence

  1. ↑ Entry on OLEAMIDE in the CosIng database of the EU Commission, accessed on December 28, 2019.
  2. ↑ a b c d Entry on oleic acid amide. In: Römpp Online . Georg Thieme Verlag, accessed on June 16, 2014.
  3. ↑ a b Oleamide data sheet from Sigma-Aldrich , accessed on April 26, 2011 ( PDF ).
  4. ↑ A. Werdehausen, H. Weiss, H. Schütt: Carboxylic acid amide preparation , Patent US 3,816,483, 1970 (Henkel).
  5. ↑ Lerner, RA. et al. (1994): Cerebrodiene: a brain lipid isolated from sleep-deprived cats . In: PNAS 91 (20); 9505-9508; PMID 7937797 ; PMC 44841 (free full text, PDF).
  6. ↑ Cravatt, BF. et al. (1995): Chemical characterization of a family of brain lipids that induce sleep. In: Science 268 (5216); 1506-1509; PMID 7770779 ; doi : 10.1126 / science.7770779 .
  7. ^ Basile, AS. et al. (1999): Characterization of the hypnotic properties of oleamide . In: Neuroreport. 10 (5); 947-951; PMID 10321465 .
  8. ↑ a b Hiley, CR. and Hoi, PM. (2007): Oleamide: a fatty acid amide signaling molecule in the cardiovascular system? In: Cardiovasc Drug Rev . 25 (1); 46-60; PMID 17445087 .
  9. ↑ Cheer, JF. et al. (1999): Modification of 5-HT2 receptor mediated behavior in the rat by oleamide and the role of cannabinoid receptors . In: Neuropharmacology . 38 (4); 533-541; PMID 10221757 ; doi : 10.1016 / S0028-3908 (98) 00208-1 .
  10. ↑ Huitrón-Reséndiz, S. et al. (2001): Effect of Oleamide on Sleep and Its Relationship to Blood Pressure, Body Temperature, and Locomotor Activity in Rats . In: Experimental Neurology 172 (1); Pp. 235-243; doi : 10.1006 / exnr.2001.7792 .
  11. ↑ Fowler, CJ. (2004): Oleamide: a member of the endocannabinoid family? In: Br J Pharmacol . 141 (2); Page 195f .; PMID 14691053 ; PMC 1574195 (free full text, PDF).
  12. ↑ O'Byrne, J. et al. (2003): The human bile acid-CoA: amino acid N-acyltransferase functions in the conjugation of fatty acids to glycine . In: J Biol Chem. 278 (36); 34237-34244; PMID 12810727 ; PDF (full text access).
  13. ↑ Chaturvedi, S. et al. (2006): In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide . In: Prostaglandins Other Lipid Mediat. 81 (3-4); 136-149; PMID 17085322 ; PMC 1712674 (free full text, PDF).
  14. ↑ Driscoll, WJ. et al. (2007): Oleamide synthesizing activity from rat kidney: identification as cytochrome c . In: J Biol Chem. 282 (31); 22353-63; PMID 17496328 ; PDF (free full text access).
  15. ↑ a b c Farrell, EK. and Merkler, DJ. (2008): Biosynthesis, degradation and pharmacological importance of the fatty acid amides. In: Drug Discov Today 13 (13-14); 558-568; PMID 18598910 ; doi : 10.1016 / j.drudis.2008.02.006 .
  16. ↑ P. Eyerer (Ed.), P. Elsner (Ed.) And T. Hirth (Ed.): The plastics and their properties . Springer-Verlag; 6. Edit again and exp. Edition 2004; ISBN 3-540-21410-0 ; P. 157.
  17. ↑ McDonald, RG. et al. (2008). Bioactive Contaminants Leach from Disposable Laboratory Plasticware . In: Science 322 (5903); Page 917; PMID 18988846 ; doi : 10.1126 / science.1162395 .