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|LipidBank=DFA0191
|LipidBank=DFA0191
|LipidMaps=LMFA01030152
|LipidMaps=LMFA01030152
|SysName=cis-9, cis-12, cis-15-Octadecatrienoic acid
|SysName=(cis-9,cis-12,cis-15) -Octadecatrienoic acid
|Common Name=&&alpha-Linolenic acid&&cis-9, cis-12, cis-15-Octadecatrienoic acid&&
|Common Name=&&(9Z,12Z,15Z) -Octadecatrienoic acid&&alpha-Linolenic acid&&
|Melting Point=-11.3 to -11°C
|Melting Point=-11.3 to -11°C
|Boiling Point=125°C at 0.05 mmHg
|Boiling Point=125°C at 0.05 mmHg
|Density=dX<sub>4</sub><sup>20</sup> 0.9164
|Density=d^{20}_4  0.9164
|Refractive=1.4678 at 50°C
|Refractive=1.4678 at 50°C
|Solubility=soluble in acetone, ethanol, ether and petroleum ether.
|Solubility=soluble in acetone, ethanol, ether and petroleum ether.<!--0400-->
|Chromatograms=Gas liquid chromatogram {{Image200|LBF18303SC01CH0001.gif}} (provided by Dr. Akiko Horiuchi).
|Chromatograms=Gas liquid chromatogram {{Image200|LBF18303SC01CH0001.gif}} (provided by Dr. Akiko Horiuchi).
|Source=Linseed, perilla, and hemp oils; drying oils.
|Source=Linseed, perilla, and hemp oils; drying oils.
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of <FONT FACE="Symbol">D</FONT>12-desaturase, and <FONT FACE="Symbol">a</FONT>-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of <FONT FACE="Symbol">D</FONT>15-desaturase. Since both <FONT FACE="Symbol">D</FONT>12- and 15-desaturases are present in plant cells, <FONT FACE="Symbol">a</FONT>-linolenic acid is synthesized in plants, and relatively enriched in leaves (photosynthetic tissues). On the other hand, these desaturases are not present in animal cells, neither linoleic nor <FONT FACE="Symbol">a</FONT>-linolenic acid is biosynthesized in animal cells in vivo. When ingested by animals, <FONT FACE="Symbol">a</FONT>-linolenic acid is desaturated, elongated and chain-shortened to form eicosapantaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA)[[Reference:Voss_A:Reinhart_M:Sankarappa_S:Sprecher_H:,J. Biol. Chem.,1991,266,19995|{{RelationTable/GetFirstAuthor|Reference:Voss_A:Reinhart_M:Sankarappa_S:Sprecher_H:,J. Biol. Chem.,1991,266,19995}}]][[Reference:Moore_SA:Hurt_E:Yoder_E:Sprecher_H:Spector_AA:,J. Lipid. Res.,1995,36,2433|{{RelationTable/GetFirstAuthor|Reference:Moore_SA:Hurt_E:Yoder_E:Sprecher_H:Spector_AA:,J. Lipid. Res.,1995,36,2433}}]]. No interconversion between the n-6 and n-3 series in mammals., Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods. Although plants synthesize and store linoleic acid and <FONT FACE="Symbol">a</FONT>-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in <FONT FACE="Symbol">a</FONT>-linolenic acid.
|Metabolism=Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of Delta 12-desaturase, and alpha -linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of Delta 15-desaturase. Since both Delta 12- and 15-desaturases are present in plant cells, alpha -linolenic acid is synthesized in plants, and relatively enriched in leaves (photosynthetic tissues). On the other hand, these desaturases are not present in animal cells, neither linoleic nor alpha -linolenic acid is biosynthesized in animal cells in vivo. When ingested by animals, alpha -linolenic acid is desaturated, elongated and chain-shortened to form eicosapantaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA)[[Reference:Voss_A:Reinhart_M:Sankarappa_S:Sprecher_H:,J. Biol. Chem.,1991,266,19995|{{RelationTable/GetFirstAuthor|Reference:Voss_A:Reinhart_M:Sankarappa_S:Sprecher_H:,J. Biol. Chem.,1991,266,19995}}]][[Reference:Moore_SA:Hurt_E:Yoder_E:Sprecher_H:Spector_AA:,J. Lipid. Res.,1995,36,2433|{{RelationTable/GetFirstAuthor|Reference:Moore_SA:Hurt_E:Yoder_E:Sprecher_H:Spector_AA:,J. Lipid. Res.,1995,36,2433}}]]. No interconversion between the n-6 and n-3 series in mammals., Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods. Although plants synthesize and store linoleic acid and alpha -linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in alpha -linolenic acid.
|Symbol=<FONT FACE="Symbol">a</FONT>LnA / C18:3n-3 / C18:3<FONT FACE="Symbol">w</FONT>3 / <FONT FACE="Symbol">a</FONT>Lnn
|Symbol= alpha LnA / C18:3n-3 / C18:3 omega 3 / alpha Lnn
|Biological Activity=Dietary <FONT FACE="Symbol">a</FONT>-linolenic acid can be further elongated and desaturated to form the long-chain n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosapentaenoic acid (DHA), which are uniquely rich in neural membranes of retina and brain in mammals. It has been reported that n-3 fatty acid deficiency produces reduced learning ability[[Reference:Yamamoto_N:Saitoh_M:Moriuchi_A:Nomura_M:Okuyama_H:,J. Lipid. Res.,1987,28,144|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_N:Saitoh_M:Moriuchi_A:Nomura_M:Okuyama_H:,J. Lipid. Res.,1987,28,144}}]], impaired vision, abnormal electroretinogram[[Reference:Neuringer_M:Connor_WE:Van_Petten_C:Barstad_L:,J. Clin. Invest.,1984,73,272|{{RelationTable/GetFirstAuthor|Reference:Neuringer_M:Connor_WE:Van_Petten_C:Barstad_L:,J. Clin. Invest.,1984,73,272}}]][[Reference:Neuringer_M:Connor_WE:Lin_DS:Barstad_L:Luck_S:,Proc. Natl. Acad. Sci. U. S. A.,1986,83,4021|{{RelationTable/GetFirstAuthor|Reference:Neuringer_M:Connor_WE:Lin_DS:Barstad_L:Luck_S:,Proc. Natl. Acad. Sci. U. S. A.,1986,83,4021}}]] and polydipsia[[Reference:Reisbick_S:Neuringer_M:Hasnain_R:Connor_WE:,Physiol. Behav.,1990,47,315|{{RelationTable/GetFirstAuthor|Reference:Reisbick_S:Neuringer_M:Hasnain_R:Connor_WE:,Physiol. Behav.,1990,47,315}}]]. Dietary fat manipulation of perilla oil rich in <FONT FACE="Symbol">a</FONT>-linolenic acid reduces colonic damage in experimental Crohn's disease [[Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,J. Gastroenterol.,1995,30 Suppl 8,98|{{RelationTable/GetFirstAuthor|Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,J. Gastroenterol.,1995,30 Suppl 8,98}}]][[Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,Am. J. Clin. Nutr.,1996,63,741|{{RelationTable/GetFirstAuthor|Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,Am. J. Clin. Nutr.,1996,63,741}}]].
|Biological Activity=Dietary alpha -linolenic acid can be further elongated and desaturated to form the long-chain n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosapentaenoic acid (DHA), which are uniquely rich in neural membranes of retina and brain in mammals. It has been reported that n-3 fatty acid deficiency produces reduced learning ability[[Reference:Yamamoto_N:Saitoh_M:Moriuchi_A:Nomura_M:Okuyama_H:,J. Lipid. Res.,1987,28,144|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_N:Saitoh_M:Moriuchi_A:Nomura_M:Okuyama_H:,J. Lipid. Res.,1987,28,144}}]], impaired vision, abnormal electroretinogram[[Reference:Neuringer_M:Connor_WE:Van_Petten_C:Barstad_L:,J. Clin. Invest.,1984,73,272|{{RelationTable/GetFirstAuthor|Reference:Neuringer_M:Connor_WE:Van_Petten_C:Barstad_L:,J. Clin. Invest.,1984,73,272}}]][[Reference:Neuringer_M:Connor_WE:Lin_DS:Barstad_L:Luck_S:,Proc. Natl. Acad. Sci. U. S. A.,1986,83,4021|{{RelationTable/GetFirstAuthor|Reference:Neuringer_M:Connor_WE:Lin_DS:Barstad_L:Luck_S:,Proc. Natl. Acad. Sci. U. S. A.,1986,83,4021}}]] and polydipsia[[Reference:Reisbick_S:Neuringer_M:Hasnain_R:Connor_WE:,Physiol. Behav.,1990,47,315|{{RelationTable/GetFirstAuthor|Reference:Reisbick_S:Neuringer_M:Hasnain_R:Connor_WE:,Physiol. Behav.,1990,47,315}}]]. Dietary fat manipulation of perilla oil rich in alpha -linolenic acid reduces colonic damage in experimental Crohn's disease [[Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,J. Gastroenterol.,1995,30 Suppl 8,98|{{RelationTable/GetFirstAuthor|Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,J. Gastroenterol.,1995,30 Suppl 8,98}}]][[Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,Am. J. Clin. Nutr.,1996,63,741|{{RelationTable/GetFirstAuthor|Reference:Shoda_R:Matsueda_K:Yamato_S:Umeda_N:,Am. J. Clin. Nutr.,1996,63,741}}]].
}}
}}


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Latest revision as of 10:39, 1 October 2010

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Upper classes: LB LBF



(9Z,12Z,15Z) -Octadecatrienoic acid
LBF18303SC01.png
Structural Information
(cis-9,cis-12,cis-15) -Octadecatrienoic acid
  • (9Z,12Z,15Z) -Octadecatrienoic acid
  • α-Linolenic acid
alpha LnA / C18:3n-3 / C18:3 omega 3 / alpha Lnn
Formula C18H30O2
Exact Mass 278.224580204
Average Mass 278.4296
SMILES CCC=CCC=CCC=CCCCCCCCC(O)=O
Physicochemical Information
-11.3 to -11°C
125°C at 0.05 mmHg
d20
4
   0.9164
1.4678 at 50°C
soluble in acetone, ethanol, ether and petroleum ether.
Linseed, perilla, and hemp oils; drying oils.
Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of Delta 12-desaturase, and alpha -linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of Delta 15-desaturase. Since both Delta 12- and 15-desaturases are present in plant cells, alpha -linolenic acid is synthesized in plants, and relatively enriched in leaves (photosynthetic tissues). On the other hand, these desaturases are not present in animal cells, neither linoleic nor alpha -linolenic acid is biosynthesized in animal cells in vivo. When ingested by animals, alpha -linolenic acid is desaturated, elongated and chain-shortened to form eicosapantaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA) Voss_A et al. Moore_SA et al.. No interconversion between the n-6 and n-3 series in mammals., Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods. Although plants synthesize and store linoleic acid and alpha -linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in alpha -linolenic acid.
Dietary alpha -linolenic acid can be further elongated and desaturated to form the long-chain n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosapentaenoic acid (DHA), which are uniquely rich in neural membranes of retina and brain in mammals. It has been reported that n-3 fatty acid deficiency produces reduced learning ability Yamamoto_N et al., impaired vision, abnormal electroretinogram Neuringer_M et al. Neuringer_M et al. and polydipsia Reisbick_S et al.. Dietary fat manipulation of perilla oil rich in alpha -linolenic acid reduces colonic damage in experimental Crohn's disease Shoda_R et al. Shoda_R et al..
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms Gas liquid chromatogram
LBF18303SC01CH0001.gif
(provided by Dr. Akiko Horiuchi).
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18303SC01 See above. Moore_SA et al. 1995
n.a. LBF18303SC01 See above. Neuringer_M et al. 1986
n.a. LBF18303SC01 See above. Neuringer_M et al. 1984
n.a. LBF18303SC01 See above. Reisbick_S et al. 1990
n.a. LBF18303SC01 See above. Shoda_R et al. 1996
n.a. LBF18303SC01 See above. Shoda_R et al. 1995
n.a. LBF18303SC01 See above. Voss_A et al. 1991
n.a. LBF18303SC01 See above. Yamamoto_N et al. 1987