LBF22603SC01: Difference between revisions

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|Solubility=soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.[[Reference:Klenk_E:Bongard_W:,Hoppe Seylers Z. Physiol. Chem.,1952,291,104|{{RelationTable/GetFirstAuthor|Reference:Klenk_E:Bongard_W:,Hoppe Seylers Z. Physiol. Chem.,1952,291,104}}]][[Reference:Klenk_E:Lindlar_F:,Hoppe Seylers Z. Physiol. Chem.,1955,299,74|{{RelationTable/GetFirstAuthor|Reference:Klenk_E:Lindlar_F:,Hoppe Seylers Z. Physiol. Chem.,1955,299,74}}]][[Reference:Whitcutt_JM:,Biochem. J.,1957,67,60|{{RelationTable/GetFirstAuthor|Reference:Whitcutt_JM:,Biochem. J.,1957,67,60}}]]
|Solubility=soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.[[Reference:Klenk_E:Bongard_W:,Hoppe Seylers Z. Physiol. Chem.,1952,291,104|{{RelationTable/GetFirstAuthor|Reference:Klenk_E:Bongard_W:,Hoppe Seylers Z. Physiol. Chem.,1952,291,104}}]][[Reference:Klenk_E:Lindlar_F:,Hoppe Seylers Z. Physiol. Chem.,1955,299,74|{{RelationTable/GetFirstAuthor|Reference:Klenk_E:Lindlar_F:,Hoppe Seylers Z. Physiol. Chem.,1955,299,74}}]][[Reference:Whitcutt_JM:,Biochem. J.,1957,67,60|{{RelationTable/GetFirstAuthor|Reference:Whitcutt_JM:,Biochem. J.,1957,67,60}}]]
|Chromatograms=Gas liquid chromatogram {{Image200|LBF22603SC01CH0002.gif}} (provided by Dr. Akiko Horiuchi).
|Chromatograms=Gas liquid chromatogram {{Image200|LBF22603SC01CH0002.gif}} (provided by Dr. Akiko Horiuchi).
|Source=South African pilchard oil; brain phosphatides; liver lipids of cattle. It is found mainly in fish and marine microorganisms and plants. DHA is also an essential component of the brain, eyes, and other nervous system tissues. Tuna eyeballs are one of the major source .
|Chemical Synthesis=
|Metabolism=Metabolic product of <FONT FACE="Symbol">a</FONT>-linolenic acid (9,12,25-18:3). The synthesis of 4,7,10,13,16,19-22:6 (=DHA) occurs via the following reaction sequence [[Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471|{{RelationTable/GetFirstAuthor|Reference:Sprecher_H:Luthria_DL:Mohammed_BS:Baykousheva_SP:,J. Lipid. Res.,1995,36,2471}}]];>: 9,12,15-18:3 --> 6,9,12,15-18:4 --> 8,11,14,17-20:4 --> 5,8,11,14,17-20:5 --> 7,10,13,16,19-22:5 --> 9,12,15,18,21-24:5 --> 6,9,12,15,18,21-24:6 --> 4,7,10,13,16,19-22:6. According to these pathways the 24-carbon acids that are made in the endoplasmic reticulum move to a site for partial beta-oxidation, which is most likely peroxisomes.
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Revision as of 22:00, 24 November 2009

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Upper classes: LB LBF



Docosahexaenoic acid
LBF22603SC01.png
Structural Information
cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid
  • Docosahexaenoic acid
  • cervonic acid
  • cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid
Formula C22H32O2
Exact Mass 328.240230268
Average Mass 328.48828000000003
SMILES C(CCC(O)=O)=CCC=CCC=CCC=CCC=CCC=CCC
Physicochemical Information
-44.2 to -44.1 °C
1.5017 at 26 °C
soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether. KlenkEet al. KlenkEet al. Whitcutt_JM
South African pilchard oil; brain phosphatides; liver lipids of cattle. It is found mainly in fish and marine microorganisms and plants. DHA is also an essential component of the brain, eyes, and other nervous system tissues. Tuna eyeballs are one of the major source .
Metabolic product of a-linolenic acid (9,12,25-18:3). The synthesis of 4,7,10,13,16,19-22:6 (=DHA) occurs via the following reaction sequence Sprecher_H et al.;>: 9,12,15-18:3 --> 6,9,12,15-18:4 --> 8,11,14,17-20:4 --> 5,8,11,14,17-20:5 --> 7,10,13,16,19-22:5 --> 9,12,15,18,21-24:5 --> 6,9,12,15,18,21-24:6 --> 4,7,10,13,16,19-22:6. According to these pathways the 24-carbon acids that are made in the endoplasmic reticulum move to a site for partial beta-oxidation, which is most likely peroxisomes.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms Gas liquid chromatogram
LBF22603SC01CH0002.gif
(provided by Dr. Akiko Horiuchi).
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF22603SC01 See above. Applegate_KR et al. 1991
n.a. LBF22603SC01 See above. Applegate_KR et al. 1991
n.a. LBF22603SC01 See above. Connor_WE et al. 1993
n.a. LBF22603SC01 See above. Horrocks_LA et al. 1999
n.a. LBF22603SC01 See above. Klenk_E et al. 1952
n.a. LBF22603SC01 See above. Klenk_E et al. 1955
n.a. LBF22603SC01 See above. Neuringer_M et al. 1986
n.a. LBF22603SC01 See above. Neuringer_M et al. 1984
n.a. LBF22603SC01 See above. Nieuwenhuys_CM et al. 1998
n.a. LBF22603SC01 See above. Okuyama_H et al. 1996
n.a. LBF22603SC01 See above. Oshima_M et al. 1995
n.a. LBF22603SC01 See above. Reisbick_S et al. 1990
n.a. LBF22603SC01 See above. Shikano_M et al. 1993
n.a. LBF22603SC01 See above. Sprecher_H et al. 1995
n.a. LBF22603SC01 See above. Takahashi_M et al. 1994
n.a. LBF22603SC01 See above. Tomobe_YI et al. 2000
n.a. LBF22603SC01 See above. Whitcutt_JM 1957
n.a. LBF22603SC01 See above. Yamamoto_N et al. 1987