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Α-Linolenic acid

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Not to be confused with linoleic acid.
This article is about alpha-linolenic acid. For other uses, see Linolenic acid.

α-Linolenic acid
Names
IUPAC name
(9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid
Other names
ALA; Linolenic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid;[1] Industrene 120
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.669 Edit this at Wikidata
UNII
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- checkY
    Key: DTOSIQBPPRVQHS-PDBXOOCHSA-N checkY
  • InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
    Key: DTOSIQBPPRVQHS-PDBXOOCHBH
  • O=C(O)CCCCCCC\C=C/C\C=C/C\C=C/CC
  • CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
Properties
C18H30O2
Molar mass 278.436 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

α-Linolenic acid (ALA) is an essential omega-3 fatty acid found in seeds (chia, flaxseed, see also table below), nuts (notably walnuts), and 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 listed by its lipid number, 18:3, and (n−3); its isomer GLA is 18:3 (n−6).

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 (GLA), a polyunsaturated n−6 (omega-6) fatty acid.

History

α-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 1930s 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 chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[7] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to large abundance of linolenic acid, that shows up as sharp resonances in high resolution carbon-13 NMR spectra, invariably.[8] Some studies state that ALA remains stable during processing and cooking.[9] However, other studies state that ALA might not be suitable for baking, as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures.[10] ALA percentages in the table below refer to the oils extracted from each item.

Common name Alternate name Linnaean name % ALA†(of oil) ref.
Chia chia sage Salvia hispanica 64% [11]
Kiwifruit seeds Chinese gooseberry Actinidia chinensis 62% [11]
Perilla shiso Perilla frutescens 58% [11]
Flax linseed Linum usitatissimum 55% [11]
Lingonberry cowberry Vaccinium vitis-idaea 49% [11]
Camelina camelina Camelina sativa 35-45%
Purslane portulaca Portulaca oleracea 35% [11]
Sea buckthorn seaberry Hippophae rhamnoides L. 32% [12]
Hemp cannabis Cannabis sativa 20% [11]
Walnut English walnut / Persian walnut Juglans regia 10.4% [13]
Rapeseed canola Brassica napus 10% [2]
Soybean soya Glycine max 8% [2]
  †average value

Potential 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. Exceptions include flaxseed (must be ground for proper nutrient absorption) and walnuts. 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 and algae 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.[14] 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.[15][16] Conversion of ALA to DHA is higher in women than in men. [17]

A large 2006 study found no association between total α-linolenic acid intake and overall risk of prostate cancer.[18] Multiple studies[19][20] have shown a relationship between α-linolenic acid and an increased risk of prostate cancer. This risk was found to be irrespective of source of origin (e.g., meat, vegetable oil).[21] A recent (2009) meta-analysis, 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.[22]

Stability and hydrogenation

α-Linolenic acid is relatively more susceptible to oxidation and will become rancid more quickly than many other oils. Oxidative instability of α-linolenic acid is one reason why producers choose to partially hydrogenate oils containing α-linolenic acid, such as soybean oil.[23] Soybeans are the largest source of edible oils in the U.S., and 40% of soy oil production is partially hydrogenated.[24][25]

However, when partially hydrogenated, part of the unsaturated fatty acids become unhealthy trans fats. Consumers are increasingly avoiding products that contain trans fats, and governments have begun to ban trans fats in food products. These regulations and market pressures have spurred the development of low-α-linolenic acid soybeans. These new soybean varieties yield a more stable oil that doesn't require hydrogenation for many applications, thus providing trans fat-free products, such as frying oil.[26]

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 linoleic acid.[27] Monsanto Company has introduced to the market Vistive, their brand of low α-linolenic acid soybeans, which is less controversial than GMO offerings, as it was created via conventional breeding techniques.

Cardiovascular

There is some evidence ALA consumption might have a slight preventative effect against cardiovascular diseases.[28] The effect only registers through fish consumption; ALA taken in capsule form has no effect.[29]

See also

References

  1. ^ Loreau, O; Maret, A; Poullain, D; Chardigny, JM; Sébédio, JL; Beaufrère, B; Noël, JP (2000). "Large-scale preparation of (9Z,12E)-1-(13)C-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-1-(13)C-octadeca-9,12,15-trienoic acid and their 1-(13)C all-cis isomers". Chemistry and physics of lipids. 106 (1): 65–78. doi:10.1016/S0009-3084(00)00137-7. PMID 10878236.
  2. ^ a b c Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (PDF). Archived from the original (pdf) on 12 February 2006. Retrieved 22 February 2006. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ Rollett, A. (1909). "Zur kenntnis der linolensäure und des leinöls". Z. Physiol. Chem. 62 (5–6): 422. doi:10.1515/bchm2.1909.62.5-6.422.
  4. ^ J. W. McCutcheon (1955). "Linolenic acid". Organic Syntheses; Collected Volumes, vol. 3, p. 351.
  5. ^ Green, TG; Hilditch, TP (1935). "The identification of linoleic and linolenic acids". Biochem. J. 29 (7): 1552–63. PMC 1266662. PMID 16745822.
  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 (3): 271–275. doi:10.1055/s-1995-3906.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ YashRoy R.C. (1987) 13-C NMR studies of lipid fatty acyl chains of chloroplast membranes. Indian Journal of Biochemistry and Biophysics vol. 24(6), pp. 177-178.https://www.researchgate.net/publication/230822408_13-C_NMR_studies_of_lipid_fatty_acyl_chains_of_chloroplast_membranes?ev=prf_pub
  9. ^ "Processing and cooking effects on lipid content and stability of alpha-linolenic acid in spaghetti containing ground flaxseed".
  10. ^ "OXIDATIVE STABILITY OF FLAXSEED LIPIDS DURING BAKING".
  11. ^ a b c d e f g Seed Oil Fatty Acids – SOFA Database Retrieval
  12. ^ Li, Thomas S. C. (1999). "Sea buckthorn: New crop opportunity". Perspectives on new crops and new uses. Alexandria, VA: ASHS Press. pp. 335–337. Archived from the original on 22 September 2006. Retrieved 28 October 2006. {{cite conference}}: Unknown parameter |booktitle= ignored (|book-title= suggested) (help); Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  13. ^ "Omega-3 fatty acids". University of Maryland Medical Center.
  14. ^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  15. ^ 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.
  16. ^ 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.
  17. ^ "Conversion of $\alpha$-linolenic acid to longer-chain polyunsaturated fatty acids in human adults".
  18. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  19. ^ 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.
  20. ^ 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.
  21. ^ 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.
  22. ^ 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.
  23. ^ Kinney, Tony. "Metabolism in plants to produce healthier food oils (slide #4)" (PDF). Retrieved 11 January 2007.
  24. ^ Fitzgerald, Anne and Brasher, Philip. "Ban on trans fat could benefit Iowa". Truth About Trade and Technology. Retrieved 3 January 2007.{{cite journal}}: CS1 maint: multiple names: authors list (link) [dead link]
  25. ^ Kinney, Tony. "Metabolism in plants to produce healthier food oils (slide #2)" (PDF). Retrieved 11 January 2007.
  26. ^ Monsanto. "ADM to process Monsanto's Vistive low linolenic soybeans at Indiana facility". Archived from the original on 11 December 2006. Retrieved 6 January 2007.
  27. ^ Kinney, Tony. "Metabolism in plants to produce healthier food oils" (PDF). Retrieved 11 January 2007.
  28. ^ Pan A, Chen M, Chowdhury R; et al. (December 2012). "α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis". Am. J. Clin. Nutr. (Systematic review). 96 (6): 1262–73. doi:10.3945/ajcn.112.044040. PMC 3497923. PMID 23076616.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  29. ^ Reiner MF, Stivala S, Camici GG, Beer JH (March 2014). "[The effects of Omega-3 fatty acids in clinical medicine]". Praxis (Bern 1994) (Review) (in German). 103 (6): 329–35. doi:10.1024/1661-8157/a001593. PMID 24618312.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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