Eicosapentaenoic acid

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Structural formula
Structure of eicosane pentaenoic acid
General
Surname Eicosapentaenoic acid
other names
  • EPA (Eicosapentaenoic acid)
  • (5 Z , 8 Z , 11 Z , 14 Z , 17 Z ) -Eicosa-5,8,11,14,17-pentanoic acid ( IUPAC )
  • Icosapentaenoic acid (IPA)
  • Timnodonic acid
  • 20: 5 (ω − 3) ( lipid name )
Molecular formula C 20 H 30 O 2
Brief description

colorless liquid

External identifiers / databases
CAS number 10417-94-4
EC number 600-528-7
ECHA InfoCard 100.117.069
PubChem 446284
ChemSpider 393682
DrugBank DB00159
Wikidata Q409990
properties
Molar mass 302.46 g mol −1
Physical state

liquid

density

0.94 g cm −3

Melting point

−54 - (- 53) ° C

solubility

soluble in methanol

Refractive index

1.4986

safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 314
P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Eicosapentaenoic acid ( EPA ) is a polyunsaturated fatty acid . It belongs to the class of omega-3 fatty acids . Their salts and esters are called eicosapentaenoates .

Occurrence

Ready-to-cook salmon, cut as a steak

Eicosapentaenoic acid is ubiquitous in living things, i. H. omnipresent. It can be found enriched in fatty sea fish such as salmon ( Salmo salar ) or Atlantic herring ( Clupea harengus ) in the form of their acylglycerols (glycerides) and phospholipids . In a few plants it occurs in such a bound form in small quantities.

properties

Eicosapentaenoic acid is a colorless oil. The five isolated double bonds are in the cis form.

Biological function

Eicosapentaenoic acid is required for many metabolic functions . It is the starting material for the formation of docosahexaenoic acid (DHA) and eicosanoids , which are essential for body functions such as the immune system , blood clotting , regulation of blood pressure and heart rate and the like. v. a. are needed. It has a positive effect on certain heart diseases ( coronary heart disease ). In a meta-analysis from 2018, no positive properties in heart disease could be demonstrated using omega-3 fatty acids.

Their biosynthesis takes place via α-linolenic acid , an essential omega-3 fatty acid. Studies have come to different results regarding the rate of conversion of α-linolenic acid into DHA and EPA. Some studies cite rather high values ​​for the conversion to EPA in healthy young women as 21% (DHA 9%), in healthy young men around 8% (DHA 0 to 4%). Other studies speak of the conversion of about 5–10% of the ingested α-linolenic acid into EPA and 2–5% into DHA, or even conversion rates into EPA and DHA less than 5%. One study concludes that vegetable oil rich in α-linolenic acid, combined with a diet low in linoleic acid , increases tissue EPA levels in a manner similar to that of supplementation with fish oil. EPA and DHA have anti-inflammatory effects by weakening the activation of the TLR4 signaling pathway.

Recent scientific studies suggest the particular importance of EPA for promoting positive emotions as well as mood enhancement and a beneficial influence on the reduction of anxiety , depression and symptoms of schizophrenia . A meta-analysis of 28 randomized controlled trials suggests that EPA is significantly more effective than DHA for treating depression .

Nutritional supplement

Since the intake of omega-3 fatty acids such as eicosapentaenoic acid and docosahexaenoic acid is well below the recommendations in Europe, EPA and DHA have been offered in the form of capsules and fortified foods for several years. For the production of eicosapentaenoic acid, fish oil is prepared from fish waste from fatty sea fish.

When processing fish oil, it is transesterified from the natural triglyceride form (TG form) into the ethyl ester form (EE form) of EPA and DHA by means of ethanol , which is then referred to as ethyl EPA (also E-EPA, EPA -E, EPA-EE, chemical name ethyl eicosapentaenoate or ethyl eicosapentaenoate, CAS number 86227-47-6). After purification and concentration by distillation, the ethyl ester form can be transesterified back into the natural triglyceride form using glycerine ("rTG" = re-esterified triglyceride). In order to save costs, many omega-3 products or EPA / DHA concentrates contain the ethyl ester forms of EPA and DHA, which are chemically no longer oil , but are often incorrectly referred to and marketed as fish oil concentrate. Some studies indicate that the bioavailability of EPA in the TG form or rTG form is higher than in the EE form.

In the meantime, some manufacturers of baby food are also adding fish oil to their products in order to meet the needs of babies for omega-3 fatty acids, which are naturally present in breast milk.

As an alternative to the fish oil preparations, Omega-3 capsules made purely from plants have also been available on the market for some time. The EPA and DHA it contains is obtained directly from algae or made up of high-quality vegetable oils such as hemp oil .

Individual evidence

  1. ↑ a b c d e f data sheet cis-5,8,11,14,17-Eicosapentaenoic acid from Sigma-Aldrich , accessed on September 5, 2013 ( PDF ).
  2. ↑ Data sheet Eicosapentaenoic Acid (PDF) from Calbiochem, accessed on December 8, 2015.
  3. ↑ 5,8,11,14,17-Eicosapentaenoic acid from PlantFA Database, accessed October 27, 2017.
  4. Jump up ↑ Robert Clarke, Jane Armitage, Sarah Lewington, Rory Collins, Jackie Bosch: Associations of Omega-3 Fatty Acid Supplement Use With Cardiovascular Disease Risks: Meta-analysis of 10 Trials Involving 77,917 Individuals . In: JAMA Cardiology . tape 3 , no. 3 , March 1, 2018, ISSN  2380-6583 , p. 225–233 , doi : 10.1001 / jamacardio.2017.5205 ( jamanetwork.com [accessed May 7, 2019]).
  5. ↑ Omega-3 fatty acid capsules useful food supplement? Retrieved May 7, 2019 .
  6. ↑ vitalstoff-lexikon.de Vitalstoff-Lexikon, overview with further sources.
  7. ↑ GC Burdge, SA Wootton: Conversion of alpha-linolenic acid to eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in young women. In: Br J Nutr. 88 (4), Oct 2002, pp. 411-420.
  8. ↑ GC Burdge, AE Jones, SA Wootton: Eicosapentaenoic and docosapentaenoic acids are the principal products of alpha-linolenic acid metabolism in young men. In: Br J Nutr. 88 (4), Oct 2002, pp. 355-363.
  9. ↑ G. Burdge: Alpha-linolenic acid metabolism in men and women: nutritional and biological implications. In: Curr Opin Clin Nutr Metab Care. 7 (2), Mar 2004, pp. 137-144.
  10. ↑ JT Brenna, N. Salem, AJ Sinclair, SC Cunnane: alpha-Linolenic acid supplementation and conversion to n-3 long-chain polyunsaturated fatty acids in humans. In: Prostaglandins, leukotriene, and essential fatty acids. Volume 80, Numbers 2-3, Feb-Mar 2009, pp. 85-91. doi: 10.1016 / j.plefa.2009.01.004 . PMID 19269799 . (Review).
  11. ↑ Breanne M Anderson, David WL Ma: Are all n-3 polyunsaturated fatty acids created equal? In: Lipids in Health and Disease. 8, 2009, p. 33, doi: 10.1186 / 1476-511X-8-33 .
  12. ↑ JT Brenna: Efficiency of conversion of alpha-linolenic acid to long chain n-3 fatty acids in man. In: Current opinion in clinical nutrition and metabolic care. Volume 5, Number 2, March 2002, pp. 127-132. PMID 11844977 .
  13. ↑ E. Mantzioris, MJ James, RA Gibson, LG Cleland: Dietary substitution with alpha-linolenic acid-rich vegetable oil Increases eicosapentaenoic acid Concentrations in tissues. In: The American journal of clinical nutrition. Volume 59, Number 6, June 1994, pp. 1304-1309. PMID 7910999 .
  14. ↑ MM Rogero, PC Calder: Obesity, Inflammation, Toll-Like Receptor 4 and Fatty Acids . In: Nutrients . tape 10 , 2018, doi : 10.3390 / nu10040432 , PMID 29601492 , PMC 5946217 (free full text) - (English).
  15. ↑ David Servan-Schreiber: The New Medicine of Emotions. Stress, anxiety, depression: getting well without medication . Goldmann, Munich 2006, ISBN 3-442-15353-0 , p. 155–156 and 319 (translator: Inge Leipold, Ursel Schäfer).
  16. ^ P. Adams, S. Lawson et al. a .: Arachidonic acid to eicosapentaenoic acid ratio in blood correlates positively with clinical symptoms of depression . In: Lipids . No. 31 , 1996, pp. 157-161 . PMID 8729112 .
  17. ↑ VK Burt, LL Altshuler a. a .: Depressive symptoms in the perimenopause: prevalence, assessment, and guidelines for treatment . In: Harvard Review of Psychiatry . No. 6 (3) , 1998, pp. 121-132 , PMID 10372280 .
  18. ↑ H. Tiemeier, HR van Tuijl u. a .: Plasma fatty acid composition and depression are associated in the elderly: the Rotterdam Study . In: American Journal of Clinical Nutrition . No. 78 , 2003, p. 40-46 .
  19. ↑ M. Peet, J. Brind, CN Ramchand, S. Shah, GK Vankar: Two double-blind placebo-controlled pilot studies of eicosapentaenoic acid in the treatment of schizophrenia . In: Schizophr. Res. Band 49 , no. 3 , 2001, p. 243-251 , PMID 11356585 .
  20. ↑ C. Song, S. Zhao: Omega-3 fatty acid eicosapentaenoic acid. A new treatment for psychiatric and neurodegenerative diseases: a review of clinical investigations. In: Expert Opin Investig Drugs. 16 (10), Oct 2007, pp. 1627-1638. PMID 17922626 .
  21. ↑ Julian G. Martens: EPA but not DHA appears to be responsible for the efficacy of omega-3 long chain polyunsaturated fatty acid supplementation in depression: evidence from a meta-analysis of randomized controlled trials. In: Journal of the American College of Nutrition. 28, 2009, pp. 525-542. PMID 20439549 (Review).
  22. ↑ Ascentahealh.com: Fish Oil Triglycerides vs. Ethyl Esters: A comparative review of absorption, stability and safety concerns ( Memento of December 31, 2015 in the Internet Archive ).
  23. ↑ J. Dyerberg, P. Madsen, JM Moller, I. Aardestrup, EB Schmidt: Bioavailability of marine n-3 fatty acid formations. In: Prostaglandins Leutkot. Essent. Fatty Acids. 83, 2010, pp. 137-141.
  24. ^ J. Neubronner, JP Schuchardt, G. Kressel, M. Merkel, C. von Schacky, A. Hahn: Enhanced increase of omega-3 index in response to long term n-3 fatty acid supplementation from triacylglycerides versus ethyl esters. In: Eur. J. Clin. Nutr. 65, 2011, pp. 247-254.
  25. ↑ B. Beckermann, M. Beneke, I. Seitz: Comparative bioavailability of eicosapentaenoic acid and docosahexaenoic acid from triglycerides, free fatty acids and ethyl esters in volunteers. In: drug research . 40, 1990, pp. 700-704.
  26. ↑ LD Lawson, BG Hughes: Human absorption of fish oil fatty acids as triacylglycerols, free acids, or ethyl esters. In: Biochem Biophys Res Commun . 152, 1988, pp. 328-335.
  27. ↑ S. el Boustani, C. Colette L. Monnier, B. Descomps, A. Crastes de Paulet, F. Mendy: Enteral absorption in one of eicosapentaenoic acid in different chemical forms. In: Lipids. 22, 1987, pp. 711-714.
  28. ↑ F. Visioli, P. Rise, MC Barassi, F. Marangoni, C. Galli: Dietary intake of fish vs. formulations leads to higher plasma concentrations of n-3 fatty acids. In: Lipids. 38, 2003, pp. 415-418.
  29. ↑ Kathrin Burger: Hype about omega-3 fatty acids. Too much fish doesn't make you healthier. In: taz . July 9, 2009.
  30. ↑ Please do not buy fish oil capsules In: PETA website, accessed January 5, 2019.

literature

Web links

Wiktionary: Eicosapentaenoic acid  - explanations of meanings, word origins, synonyms, translations