Back to HOME

Fatty acid


DATA No : DFA0224 INFORMANT : Tetsuyuki Kobayashi

NAME : cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid

COMMON NAME: Docosahexaenoic acid / cervonic acid
SYMBOL: DHA / C22:6n-3 / C22:6w3
FORMULA: C22H32O2 MOL.WT (average) : 328.488


Download ChemDraw structure data
Download Mol format file
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 (Ref. 2005), impaired vision, abnormal electroretinogram (Ref. 2006/2007) and polydipsia (Ref. 2008). It is believed to be important for the full development of the nervous system in the fetus and newborn.(Ref. 2003) Considered, along with EPA, to be the major reason for the beneficial effects of fish oils on the cardiovascular system. Anti-inflammatory (Ref. 2021/2022/2024), anti-thrombotic (Ref. 2023), anti-arteriosclerosis (Ref. 2022/2025) and anti-cancer activities (Ref. 2026/2027) have been reported. Production of bioactive metabolites, eicosanoids, is suppressed by DHA. DHA can be also involved in the modulation of membrane structures (Ref. 2017/2018).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:-44.2 to -44.1 degC

BOILING POINT:

REFRACTIVE INDEX:1.5017 at 26 degC

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.(Ref. 0292)(Ref. 0294)(Ref. 0526)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
Gas liquid chromatogram
[Chromatogram 0002] (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 (Ref. 2012).
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 (Ref. 2013): 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.
GENETIC INFORMATION

NOTE

REFERENCES
[0292]
AUTHOR:Klenk, E., and Bongard, W.
TITLE:[Constitution of the unsaturated C20 and C22 fatty acids of the glycophosphatides of the brain.] PubMed ID:12999186
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:291 PAGE : 104-118 (1952)
[TOP]

[0294]
AUTHOR:Klenk, E., and Lindlar, F.
TITLE:[On the docosapolyenic acids of glycerol phosphatides of the brain.] PubMed ID:14353466
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:299 PAGE : 74-84 (1955)
[TOP]

[0526]
AUTHOR:Whitcutt, J. M.
TITLE:South African pilchard oil. 6. The isolation and structure of a docosahexaenoic acid from South African pilchard oil PubMed ID:13471511
JOURNAL:Biochem J.
VOL:67 PAGE : 60-64 (1957)
[TOP]

[2003]
AUTHOR:Okuyama, H., Kobayashi, T., and Watanabe, S.
TITLE:Dietary fatty acids--the N-6/N-3 balance and chronic elderly diseases. Excess linoleic acid and relative N-3 deficiency syndrome seen in Japan PubMed ID:9246358
JOURNAL:Prog Lipid Res.
VOL:35 PAGE : 409-457 (1996)
[TOP]

[2005]
AUTHOR:Yamamoto, N., Saitoh, M., Moriuchi, A., Nomura, M., and Okuyama, H.
TITLE:Effect of dietary alpha-linolenate/linoleate balance on brain lipid compositions and learning ability of rats PubMed ID:2883248
JOURNAL:J Lipid Res.
VOL:28 PAGE : 144-151 (1987)
[TOP]

[2006]
AUTHOR:Neuringer, M., Connor, W. E., Van Petten, C., and Barstad, L.
TITLE:Dietary omega-3 fatty acid deficiency and visual loss in infant rhesus monkeys PubMed ID:6317716
JOURNAL:J Clin Invest.
VOL:73 PAGE : 272-276 (1984)
[TOP]

[2007]
AUTHOR:Neuringer, M., Connor, W. E., Lin, D. S., Barstad, L., and Luck, S.
TITLE:Biochemical and functional effects of prenatal and postnatal omega 3 fatty acid deficiency on retina and brain in rhesus monkeys PubMed ID:3459166
JOURNAL:Proc Natl Acad Sci U S A.
VOL:83 PAGE : 4021-4025 (1986)
[TOP]

[2008]
AUTHOR:Reisbick, S., Neuringer, M., Hasnain, R., and Connor, W. E.
TITLE:Polydipsia in rhesus monkeys deficient in omega-3 fatty acids PubMed ID:2159161
JOURNAL:Physiol Behav.
VOL:47 PAGE : 315-323 (1990)
[TOP]

[2012]
AUTHOR:Kazunaga Yazawa and Haruo Kageyama
TITLE:
JOURNAL:Yukagaku
VOL:40 PAGE : 974 - (1991)
[TOP]

[2013]
AUTHOR:Sprecher, H., Luthria, D. L., Mohammed, B. S., and Baykousheva, S. P.
TITLE:Reevaluation of the pathways for the biosynthesis of polyunsaturated fatty acids PubMed ID:8847474
JOURNAL:J Lipid Res.
VOL:36 PAGE : 2471-2477 (1995)
[TOP]

[2017]
AUTHOR:Applegate, K. R., and Glomset, J. A.
TITLE:Effect of acyl chain unsaturation on the packing of model diacylglycerols in simulated monolayers PubMed ID:1797945
JOURNAL:J Lipid Res.
VOL:32 PAGE : 1645-1655 (1991)
[TOP]

[2018]
AUTHOR:Applegate, K. R., and Glomset, J. A.
TITLE:Effect of acyl chain unsaturation on the conformation of model diacylglycerols: a computer modeling study PubMed ID:1797944
JOURNAL:J Lipid Res.
VOL:32 PAGE : 1635-1644 (1991)
[TOP]

[2021]
AUTHOR:Tomobe, Y. I., Morizawa, K., Tsuchida, M., Hibino, H., Nakano, Y., and Tanaka, Y.
TITLE:Dietary docosahexaenoic acid suppresses inflammation and immunoresponses in contact hypersensitivity reaction in mice PubMed ID:10695925
JOURNAL:Lipids.
VOL:35 PAGE : 61-69 (2000)
[TOP]

[2022]
AUTHOR:Horrocks, L. A., and Yeo, Y. K.
TITLE:Health benefits of docosahexaenoic acid (DHA) PubMed ID:10479465
JOURNAL:Pharmacol Res.
VOL:40 PAGE : 211-225 (1999)
[TOP]

[2023]
AUTHOR:Nieuwenhuys, C. M., and Hornstra, G.
TITLE:The effects of purified eicosapentaenoic and docosahexaenoic acids on arterial thrombosis tendency and platelet function in rats PubMed ID:9487152
JOURNAL:Biochim Biophys Acta.
VOL:1390 PAGE : 313-322 (1998)
[TOP]

[2024]
AUTHOR:Shikano, M., Masuzawa, Y., and Yazawa, K.
TITLE:Effect of docosahexaenoic acid on the generation of platelet-activating factor by eosinophilic leukemia cells, Eol-1 PubMed ID:8468486
JOURNAL:J Immunol.
VOL:150 PAGE : 3525-3533 (1993)
[TOP]

[2025]
AUTHOR:Connor, W. E., DeFrancesco, C. A., and Connor, S. L.
TITLE:N-3 fatty acids from fish oil. Effects on plasma lipoproteins and hypertriglyceridemic patients PubMed ID:8352438
JOURNAL:Ann N Y Acad Sci.
VOL:683 PAGE : 16-34 (1993)
[TOP]

[2026]
AUTHOR:Oshima, M., Takahashi, M., Oshima, H., Tsutsumi, M., Yazawa, K., Sugimura, T., Nishimura, S., Wakabayashi, K., and Taketo, M. M.
TITLE:Effects of docosahexaenoic acid (DHA) on intestinal polyp development in Apc delta 716 knockout mice PubMed ID:7586174
JOURNAL:Carcinogenesis.
VOL:16 PAGE : 2605-2607 (1995)
[TOP]

[2027]
AUTHOR:Takahashi, M., Minamoto, T., Yamashita, N., Kato, T., Yazawa, K., and Esumi, H.
TITLE:Effect of docosahexaenoic acid on azoxymethane-induced colon carcinogenesis in rats PubMed ID:8062213
JOURNAL:Cancer Lett.
VOL:83 PAGE : 177-184 (1994)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.