alpha-Linolenic acid


alpha-Linolenic acid
α-Linolenic acid
Identifiers
CAS number 463-40-1 YesY
PubChem 5280934
ChemSpider 4444437 YesY
UNII 0RBV727H71 YesY
DrugBank DB00132
ChEBI CHEBI:27432 YesY
ChEMBL CHEMBL8739 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C18H30O2
Molar mass 278.43 g mol−1
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

α-Linolenic acid is an organic compound found in many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is given the name 18:3 (n−3).

α-Linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of gamma-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid.

Contents

History

Alpha-linolenic acid was first isolated by Rollett[3] as cited in J. W. McCutcheon's synthesis in 1942,[4] and referred to in Green and Hilditch's 1930's survey.[5] It was first artificially synthesized in 1995 from C6 homologating agents. A Wittig reaction of the phosphonium salt of [(Z-Z)-nona-3,6-dien-1-yl]triphenylphosphonium bromide with methyl 9-oxononanoate, followed by saponification, completed the synthesis.[6]

Dietary sources

Seed oils are the richest sources of α-linolenic acid, notably those of rapeseed (canola), soybeans, walnuts, flaxseed (linseed oil), perilla, chia, and hemp. α-Linolenic acid is also obtained from the thylakoid membranes of the green leaves of broadleaf plants (the membranes responsible for photosynthesis).[7] The α-linolenic acid itself is suitable for many cooking purposes, at least as much as other minimally suitable cooking oils (such as butter, to which it is thermally superior), as it can withstand temperatures up to 350 degrees F (177 degrees Celsius) for 2 hours.[8]

Common name Alternate name Linnaean name % ALA ref.
Chia chia sage Salvia hispanica 64% [9]
Kiwifruit seeds Chinese gooseberry Actinidia chinensis 62% [9]
Perilla shiso Perilla frutescens 58% [9]
Flax linseed Linum usatissimum 55% [9]
Lingonberry cowberry Vaccinium vitis-idaea 49% [9]
Purslane portulaca Portulaca oleracea 35% [9]
Sea buckthorn seaberry Hippophae rhamnoides L. 32% [10]
Hemp cannabis Cannabis sativa 20% [9]
Rapeseed canola Brassica napus 10% [2]
Soybean soya Glycine max 8% [2]
  average val

Role in nutrition and health

Flax is a rich source of α-linolenic acid.

α-Linolenic acid, an n−3 fatty acid, is a member of the group of essential fatty acids (EFAs), so called because they cannot be produced within the body and must be acquired through diet. Most seeds and seed oils are much richer in an n−6 fatty acid, linoleic acid. Linoleic acid is also an EFA, but it, and the other n−6 fatty acids, compete with n−3s for positions in cell membranes and have very different effects on human health. (See Essential fatty acid interactions.)

α-Linolenic acid can only be obtained by humans through their diets because the absence of the required 12- and 15-desaturase enzymes makes de novo synthesis from stearic acid impossible. Eicosapentaenoic acid (EPA; 20:5, n−3) and docosahexaenoic acid (DHA; 22:6, n−3) are readily available from fish oil and play a vital role in many metabolic processes. These can also be synthesized by humans from dietary α-linolenic acid, but with an efficiency of only a few percent.[11] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[12][13]

Linoleic acid (LA; 18:2, n−6) is generally assumed to reduce EPA synthesis because of the competition between α-linolenic acid and LA for common desaturation and elongation enzymes.[citation needed]

Studies have found evidence α-linolenic acid is related to a lower risk of cardiovascular disease.[14][15]

A 2005 study found that daily administration of α-linolenic acid significantly reduced both self-reported anxiety, stress levels, and objective measured cortisol levels in college age students.[16]

A large 2006 study found no association between total α-linolenic acid intake and overall risk of prostate cancer.[17] Multiple studies[18][19] have shown a relationship between alpha-linolenic acid (ALA), which is abundant in linseed oil, and an increased risk of prostate cancer. This risk was found to be irrespective of source of origin (e.g. meat, vegetable oil).[20] A recent (2009) metastudy, however, found evidence of publication bias in earlier studies, and concluded that if ALA contributes to increased prostate cancer risk, the increase in risk is quite small.[21]

Research has also suggested a major neuroprotective effect of α-linolenic acid in in vivo models of both global ischemia and KA-induced epilepsy;[22] however, if sourced from flax seed oil, residues may have adverse effect due to its content of neurotoxic cyanogen glycosides and immunosuppressive cyclic nonapeptides.[23]

A 2011 longitudinal study of over 50,000 women, conducted at Harvard University, over a period of ten years, found that a higher intake of α-Linolenic acid (combined with a lower intake of linoleic acid) was positively associated with a significant reduction in depression in the same group (the same study also found that by contrast an intake of EPA and DPA found in fish oils did not reduce depression). [24]

Hydrogenation

For manufacturers to achieve desirable traits, such as texture, spreadability and mouth feel, as well as to increase shelf life of products, unsaturated vegetable oils are often hydrogenated. Hydrogenation involves reacting the oils with hydrogen gas under pressure and high heat with the aid of a catalyst such as platinum oxide. Fully hydrogenated fatty acids become saturated fatty acids, although as fats they are not suitable for use in food, as they are as hard as wax due to the chain lengths of the original unsaturated fatty acids in the vegetable oils. Instead, oils are often only partially hydrogenated. When partially hydrogenated, part of the unsaturated fatty acids become unhealthy trans fats.

Soybeans are the largest source of edible oils in the U.S., and 40% of soy oil production is partially hydrogenated.[25][26] The low oxidative stability of α-linolenic acid is one reason for producers deciding to partially hydrogenate soybean oil.[27]

Regulations forcing the listing or banning of trans fats have spurred the development of low-α-linolenic acid soybeans. These yield a more stable oil requiring hydrogenation in fewer products, and therefore providing trans fat-free alternatives for many applications, such as frying oil.[28] Several consortia are bringing low-α-linolenic acid soy to market. DuPont's effort involves silencing the FAD2 gene that codes for Δ6-desaturase, giving a soy oil with very low levels of both α-linolenic acid and LA.[29] Monsanto Company has introduced to the market Vistive, their brand of low α-linolenic acid soybeans, which is less controversial than most GMO Monsanto offerings, as it was created via conventional breeding techniques.

Cardiovascular

Dietary α-linolenic acid has been assessed for its role in cardiovascular health. Clinical benefits have been seen in some, but not all, studies. Still, a review in 2005 concluded "The weight of the evidence favors recommendations for modest dietary consumption of α-linolenic acid (2 to 3 g per day) for the primary and secondary prevention of coronary heart disease."[30]

Drying oils

α-Linolenic acid is the most abundant unsaturated component of several drying oils (e.g. perilla, walnut and linseed oils.)

See also

References

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  2. ^ a b c Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (pdf). http://www.iupac.org/publications/pac/2001/pdf/7304x0685.pdf. Retrieved 22 February 2006. 
  3. ^ Rollett, A. (1909). Z. Physiol. Chem. 62: 422. 
  4. ^ J. W. McCutcheon (1955), "Linolenic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0531 ; Coll. Vol. 3: 351 
  5. ^ Green, TG; Hilditch, TP (1935). "The identification of linoleic and linolenic acids". Biochem. J. 29 (7): 1552–63. PMC 1266662. PMID 16745822. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1266662. 
  6. ^ Sandri, J.; Viala, J. (1995). "Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: synthesis of alpha-linolenic acid". Synthesis 3: 271–275. 
  7. ^ Chapman, David J.; De-Felice, John and Barber, James (May 1983). "Growth Temperature Effects on Thylakoid Membrane Lipid and Protein Content of Pea Chloroplasts 1". Plant Physiol 72 (1): 225–228. doi:10.1104/pp.72.1.225. PMC 1066200. PMID 16662966. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1066200. Retrieved 2007-01-15. 
  8. ^ http://www.aaoobfoods.com/graininfo.htm
  9. ^ a b c d e f g Seed Oil Fatty Acids - SOFA Database Retrieval
  10. ^ Li, Thomas S. C. (1999). "Sea buckthorn: New crop opportunity". Perspectives on new crops and new uses. Alexandria, VA: ASHS Press. pp. 335–337. http://www.hort.purdue.edu/newcrop/proceedings1999/v4-335.html. Retrieved 2006-10-28. 
  11. ^ Breanne M Anderson and David WL Ma (2009). "Are all n-3 polyunsaturated fatty acids created equal?". Lipids in Health and Disease 8 (33): 33. doi:10.1186/1476-511X-8-33. 
  12. ^ Shiels M. Innis (2007). "Fatty acids and early human development". Early Human Development 83 (12): 761–766. doi:10.1016/j.earlhumdev.2007.09.004. PMID 17920214. 
  13. ^ Burdge, GC; Calder, PC (2005). "Conversion of alpha-linolenic acid to longer-chain polyunsaturated fatty acids in human adults.". Reproduction, nutrition, development 45 (5): 581–97. doi:10.1051/rnd:2005047. PMID 16188209. 
  14. ^ Penny M. Kris-Etherton, William S. Harris, [and] Lawrence J. Appel, for the Nutrition Committee (2002). "Fish Consumption, Fish Oil, Omega-3 Fatty Acids, and Cardiovascular Disease". Circulation 106 (21): 2747–2757. doi:10.1161/01.CIR.0000038493.65177.94. PMID 12438303. 
  15. ^ William E. Connor (2000). "Importance of n−3 fatty acids in health and disease". American Journal of Clinical Nutrition 71 (1 Suppl.): 171S–175S. PMID 10617967. 
  16. ^ Yehuda S., Rabinovitz S., Mostofsky D.I. (2005). "Mixture of essential fatty acids lowers test anxiety". Nutritional Neuroscience 8 (4): 265–267. doi:10.1080/10284150500445795. PMID 16491653. 
  17. ^ Koralek DO, Peters U, Andriole G, et al. (2006). "A prospective study of dietary α-linolenic acid and the risk of prostate cancer (United States)". Cancer Causes Control 17 (6): 783–791. doi:10.1007/s10552-006-0014-x. PMID 16783606. 
  18. ^ Ramon, JM; Bou, R; Romea, S; Alkiza, ME; Jacas, M; Ribes, J; Oromi, J (2000). "Dietary fat intake and prostate cancer risk: a case-control study in Spain.". Cancer causes & control : CCC 11 (8): 679–85. doi:10.1023/A:1008924116552. PMID 11065004. 
  19. ^ Brouwer, IA; Katan, MB; Zock, PL (2004). "Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis.". The Journal of nutrition 134 (4): 919–22. PMID 15051847. 
  20. ^ De Stéfani, E; Deneo-Pellegrini, H; Boffetta, P; Ronco, A; Mendilaharsu, M (2000). "Alpha-linolenic acid and risk of prostate cancer: a case-control study in Uruguay.". Cancer Epidemiology, Biomarkers & Prevention 9 (3): 335–8. PMID 10750674. 
  21. ^ Simon, JA; Chen, YH; Bent, S (2009). "The relation of alpha-linolenic acid to the risk of prostate cancer". American Journal of Clinical Nutrition 89 (5): 1558S–1564S. doi:10.3945/ajcn.2009.26736E. PMID 19321563. 
  22. ^ Inger Lauritzen, Nicolas Blondeau, Catherine Heurteaux, Catherine Widmann, Georges Romey and Michel Lazdunski (2000). "Polyunsaturated fatty acids are potent neuroprotectors". The EMBO Journal 19 (8): 1784–1793. doi:10.1093/emboj/19.8.1784. PMC 302016. PMID 10775263. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=302016. 
  23. ^ [1], "WO 2006137717 EDIBLE FLAXSEED OIL WHICH SATURATED FATTY ACID AND TOXIC COMPONENTS WERE REMOVED THEREFROM AND PREPARATIVE PROCESS THEREOF" 
  24. ^ M. Lucas, F. Mirzaei, E. J. O'Reilly, A. Pan, W. C. Willett, I. Kawachi, K. Koenen, and A. Ascherio (2011). "Dietary intake of n-3 and n-6 fatty acids and the risk of clinical depression in women: a 10-y prospective follow-up study". Am J Clin Nutr 93 (6). doi:10.3945/ajcn.111.011817. PMC 3095504. PMID 21471279. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3095504. 
  25. ^ Fitzgerald, Anne and Brasher, Philip. "Ban on trans fat could benefit Iowa". Truth About Trade and Technology. http://www.truthabouttrade.org/article.asp?id=6669. Retrieved January 3, 2007. [dead link]
  26. ^ Kinney, Tony. "Metabolism in Plants to Produce Healthier Food Oils (slide #2)" (PDF). http://www.metabolicengineering.gov/me2005/Kinney.pdf. Retrieved 2007-01-11. 
  27. ^ Kinney, Tony. "Metabolism in Plants to Produce Healthier Food Oils (slide #4)" (PDF). http://www.metabolicengineering.gov/me2005/Kinney.pdf. Retrieved 2007-01-11. 
  28. ^ Monsanto. "ADM To Process Monsanto's VISTIVE Low Linolenic Soybeans At Indiana Facility". Archived from the original on 2006-12-11. http://web.archive.org/web/20061211071206/http://www.monsanto.com/monsanto/layout/media/06/01-12-06.asp. Retrieved 2007-01-06. 
  29. ^ Kinney, Tony. "Metabolism in Plants to Produce Healthier Food Oils" (PDF). http://www.metabolicengineering.gov/me2005/Kinney.pdf. Retrieved 2007-01-11. 
  30. ^ Mozaffarian D (2005). "Does α-linolenic acid intake reduce the risk of coronary heart disease? A review of the evidence". Alternative therapies in health and medicine 11 (3): 24–30; quiz 31, 79. PMID 15945135. 

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