Docosahexaenoic Acid (DHA)

2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA

Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected]

Product Information Docosahexaenoic Acid (DHA)

Identification Product Number DHA-GP-xxx CAS Number 6217-54-5 EN Number N/A Common Name Docosahexaenoic acid Systematic Name (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid Alternative Names DHA; Cervonic acid Storage Temperature -80°C or lower

Characteristics Specifications

Molecular Formula C22H32O2 Purity ≥ 99 % Molecular Weight 328.49 g/mol Form Liquid above -44°C Melting Point -44°C Color Clear, colorless Density 0.950 g/mL at 25°C (lit.)

Precautions & Disclaimer For laboratory use only. Not for use on humans. Not for drug, household or other uses.

Handling & Preparation Instructions

This purified fatty acid is liquid at room temperature (oil) and not soluble in water. The product is supplied sterile. It can be solubilized in undiluted serum, ethanol or DMSO. The solubility of Docosahexaenoic acid in ethanol is at least 100 mg/ml. Docosahexaenoic acid has a solubility of 1 mg/ml in a solution of 0.15 M Tris-HCL (pH 8.5). We strongly recommend using fresh preparation each day when aqueous buffers are involved. Essential fatty acids are also soluble in chloroform or ether. However those two organic solvents not recommended with the use of cells. After reconstitution, the product can be aliquoted and stored at -80°C. We recommend adding the essential fatty acids cocktail to the medium the day of use.

The concentration to add to the culture is to be determined by the user. As a starting point, we provide some references from the literature. GPR120 is a cell receptor for Docosahexaenoic acid and its expressed in several cell types, including adipocytes and macrophages. Docosahexaenoic acid stimulation of the GPR120 cell receptor was shown to inhibit the TLR2/3/4 and TNF- α pro-inflammatory cascade in a β-arrestin2 dependent fashion at 100 μM [1].

Storage

Polyunsaturated fatty acids are sensitive to oxidation, light and heat. The vacuum amber glass ampoule is optimal to prevent premature degradation. The product must be stored under -80°C and freeze-thaw cycles should be avoided. The product is stable in its ampoule at -80°C for at least 12 months.

About essential fatty acids and derivatives

Omega (ω) -3 and ω -6 fatty acids are essential to maintain the homoeostasis of the human body. Linoleic and α-linolenic acids are considered the only two essential fatty acids because they cannot be synthetized by animals. Therefore, they have to be accumulated from food because mammals lack the appropriate enzyme to perform the carbon desaturation beyond carbons 9 and 10 to introduce a double bond. However, humans can synthesize long-chain (20 carbons or more) ω-6 fatty acids from the © 2017, SiliCycle Inc. Printed in Canada 2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA

Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected]

parent fatty acid linoleic acid and long-chain ω-3 fatty acids from the parent fatty acid α-Linolenic acid. Fatty acids are the constituent of the hydrophobic tail of phospholipids that form the cell membrane. When polyunsaturated fatty acids (PUFAs) are used to form phospholipids, the curvature in their structure creates spacing between them, allowing the increase of lateral movements of transmembrane proteins. Movement of membrane proteins, such as receptors, integrins and ion channels, is fundamental to their function. PUFAs are also essential precursors of the eicosanoid family of hormones.

Supplementation with ω-3 fatty acids has been shown to reduce inflammation and increase microglial phagocytosis in a model of multiple sclerosis [2]; to suppress the pathological phenotype of human bronchial epithelial cells in a model of cystic fibrosis [3]; and to protect photoreceptors from oxidation-induced apoptosis in rats retinal neuron cells [4]. These in vitro studies demonstrate that various cell types do benefit from supplementation with essential fatty acids, not only adipocytes.

The beneficial effects of essential fatty acid supplementation have been well documented in vivo as well. For example, clinical studies have demonstrated that a diet rich in ω-3 fatty acids can reduce inflammation in obese pregnant women [5] and reduce the progression of Alzheimer’s disease [6].

About Docosahexaenoic Acid

Docosahexaenoic acid is an ω-3 PUFA. Docosahexaenoic acid is essential for the growth and functional development of the brain in infants. Docosahexaenoic acid is also required for the maintenance of normal brain function in adults. The inclusion of Docosahexaenoic acid in the diet improves learning abilities, whereas deficiencies in Docosahexaenoic acid are associated with deficits in learning [7]. Higher Docosahexaenoic acid levels in middle-aged adults are related to better performance on tests of nonverbal reasoning and mental flexibility, working memory, and vocabulary [8]. Docosahexaenoic acid levels were shown to be reduced in the brain tissue of severely depressed patients [9, 10] and its deficiency is associated with cognitive decline [11]. Some studies in rodents have suggested that Docosahexaenoic acid has protective effects against Alzheimer’s disease [12, 13].

In humans, the Docosahexaenoic acid can be obtained from the diet and, in a limited fashion, from the metabolism of Eicosapentaenoic and Docosapentaenoic acids. Within the Sprecher pathway, which occurs in vivo for the production of Docosahexaenoic acid, there is elongation of the Docosapentaenoic acid molecule, saturation via the Δ6-desaturase acting on the C24 fatty acid substrate, and a peroxisomal chain shortening step [14-18].

Thank you for choosing a SiliCycle product. Customer service is our priority and we give our best to answer your needs. If you have any questions or need further information, please contact us at [email protected] and our team of cell biologists will be delighted to respond quickly.

References

[1] Oh DY, et al. (2010) GPR120 is an omega-3 fatty acid receptor mediating potent anti-inflammatory and insulin-sensitizing effects Cell [2] Chen S, et al. (2014) n-3 PUFA supplementation benefits microglial responses to myelin pathology Sci Rep [3] Njoroge SW, et al. (2012) DHA and EPA reverse cystic fibrosis-related FA abnormalities by suppressing FA desaturase expression and activity J Lipid Res [4] Simon MV, et al. (2016) Synthesis of Docosahexaenoic acid from eicosapentaenoic acid in retina neurons protects photoreceptors from oxidative stress J Neurochem [5] Haghiac M, et al. (2015) Dietary Omega-3 Fatty Acid Supplementation Reduces Inflammation in Obese Pregnant Women: A Randomized Double-Blind Controlled Clinical Trial PLoS One [6] Wang X, et al. (2015) Effects of n-3 FA supplementation on the release of proresolving lipid mediators by blood mononuclear cells: the OmegAD study J Lipid Res [7] Horrocks LA, et al. (1999) Health benefits of Docosahexaenoic acid (DHA) Pharmacol Res [8] Muldoon MF, et al. (2010) Serum phospholipid docosahexaenonic acid is associated with cognitive functioning during middle adulthood J Nutr [9] McNamara RK, et al. (2013) Lower Docosahexaenoic acid concentrations in the postmortem prefrontal cortex of adult depressed suicide victims compared with controls without cardiovascular disease J Psychiatr Res [10] McNamara RK, et al. (2007) Selective deficits in the omega-3 fatty acid Docosahexaenoic acid in the postmortem orbitofrontal cortex of patients with major depressive disorder Biol Psychiatry [11] Lukiw WJ, et al. (2005) A role for Docosahexaenoic acid-derived neuroprotectin D1 in neural cell survival and Alzheimer disease J Clin Invest [12] Calon F, et al. (2004) Docosahexaenoic acid protects from dendritic pathology in an Alzheimer's disease mouse model Neuron [13] Hashimoto M, et al. (2006) Docosahexaenoic acid-induced protective effect against impaired learning in amyloid beta-infused rats is associated with increased synaptosomal membrane fluidity Clin Exp Pharmacol Physiol [14] Qiu X (2003) Biosynthesis of Docosahexaenoic acid (DHA, 22:6-4, 7,10,13,16,19): two distinct pathways Prostaglandins Leukot Essent Fatty Acids [15] Zhu G, et al. (2013) A more desirable balanced polyunsaturated fatty acid composition achieved by heterologous expression of Delta15/Delta4 desaturases in mammalian cells PLoS One [16] Voss A, et al. (1991) The metabolism of 7,10,13,16,19-docosapentaenoic acid to 4,7,10,13,16,19-Docosahexaenoic acid in rat liver is independent of a 4-desaturase J Biol Chem [17] Burdge GC, et al. (2002) Eicosapentaenoic and docosapentaenoic acids are the principal products of alpha-linolenic acid metabolism in young men* Br J Nutr [18] Burdge GC, et al. (2002) Conversion of alpha-linolenic acid to eicosapentaenoic, docosapentaenoic and Docosahexaenoic acids in young women Br J Nutr