LBF22603SC01

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Fatty acid (脂肪酸)

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Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA0224
LipidMaps	LMFA01030185
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF22603SC01

Docosahexaenoic acid
Structural Information
Systematic Name	cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid
Common Name	Docosahexaenoic acid cervonic acid cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid
Symbol	DHA / C22:6n-3 / C22:6w3
Formula	C22H32O2
Exact Mass	328.240230268
Average Mass	328.48828000000003
SMILES	C(CCC(O)=O)=CCC=CCC=CCC=CCC=CCC=CCC
Physicochemical Information
Melting Point	-44.2 to -44.1 °C
Boiling Point
Density
Optical Rotation
Refractive Index	1.5017 at 26 °C
Solubility	soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether. KlenkEet al. KlenkEet al. Whitcutt_JM
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 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.
Biological Activity	DHA is one of the n-3 (w3) fatty acids. It is uniquely rich in neural membranes of retina and brain in mammals. n-3 fatty acid deficiency causes the reduction of DHA level in these tissues and 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.. It is believed to be important for the full development of the nervous system in the fetus and newborn. Okuyama_H et al. <http://www.focusnewsletter.org/dha.htm> <http://www.flax.com/library/Default.htm> Considered, along with EPA, to be the major reason for the beneficial effects of fish oils on the cardiovascular system. <http://www.omegadha.com/pages/dhastory.htm> Anti-inflammatory Tomobe_YI et al. Horrocks_LA et al. Shikano_M et al., anti-thrombotic Nieuwenhuys_CM et al., anti-arteriosclerosis Horrocks_LA et al. Connor_WE et al. and anti-cancer activities Oshima_M et al. Takahashi_M et al. have been reported. Production of bioactive metabolites, eicosanoids, is suppressed by DHA. DHA can be also involved in the modulation of membrane structures Applegate_KR et al. Applegate_KR et al..
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms	Gas liquid chromatogram (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