This product is packaged as a neat oil in an all-glass ampule, and it would be best to keep it in that ampule until it is time to use the product, to prevent oxidation. Once the ampule is broken open, manipulations (transfer, dissolving, making aliquots) should be done quickly. Either plastic or glass pipettes and vials can be used.
D2534
cis-4,7,10,13,16,19-Docosahexaenoic acid
≥98%
Synonym(s):
DHA
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About This Item
Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
Molecular Weight:
328.49
Beilstein:
1715505
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.
Recommended Products
biological source
algae
Assay
≥98%
form
liquid
functional group
carboxylic acid
lipid type
omega FAs
shipped in
dry ice
storage temp.
−20°C
SMILES string
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O
InChI
1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI key
MBMBGCFOFBJSGT-KUBAVDMBSA-N
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General description
Docosahexaenoic acid (DHA) is abundantly present in the brain.
Docosahexaenoic acid (DHA) is an omega-3 polyunsaturated fatty acid with 22 carbons and six double bonds, the first double bond occurring at position three from the methyl terminus (22:6 n-3). It is a component of lipid membranes and myelin sheath.
Application
cis-4,7,10,13,16,19-Docosahexaenoic acid has been used:
- as a component in Dulbecco′s modified Eagle medium (DMEM) for culturing cells to perform docosahexaenoic acid (DHA) treatment
- to study its impact on human induced pluripotent stem cell (iPSC)-derived neuronal at a molecular and cellular level
- in MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay to study its cytotoxic effects on three human hepatocellular carcinoma (HCC) cell lines (HepG2, Hep3B, Huh7)
Biochem/physiol Actions
Docosahexaenoic acid (DHA) participates in the growth and physiology of the central nervous system. It regulates adult neurogenesis and neuroplasticity. DHA plays a key role in fetal brain development. It may exhibit antioxidant and anti-inflammatory properties. DHA plays a role in the regulation of cell membrane fluidity. It plays a vital role in several brain development processes, including neurotransmitter release, gene expression, myelination, neuroinflammation, and neuronal differentiation. DHA possesses an anticancer effect in several types of cancer.
Docosahexaenoic acid (DHA) serves as a precursor for signaling molecules such as prostaglandins and eicosanoids.
Packaging
Sealed ampule.
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
143.6 °F - closed cup
Flash Point(C)
62 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Customers Also Viewed
M Martínez
Neurology, 40(8), 1292-1298 (1990-08-01)
In confirmation of previous findings, patients with Zellweger's syndrome had extremely low levels of docosahexaenoic acid (22:6 omega 3) in the brain, liver, and kidneys. The other product of delta 4 desaturation, 22:5 omega 6, was also very significantly decreased
J L Tremoleda et al.
European journal of nuclear medicine and molecular imaging, 43(9), 1710-1722 (2016-05-08)
Traumatic spinal cord injury (SCI) is a devastating condition which affects millions of people worldwide causing major disability and substantial socioeconomic burden. There are currently no effective treatments. Modulating the neuroinflammatory (NI) response after SCI has evolved as a major
G Kargas et al.
Journal of chromatography, 526(2), 331-340 (1990-04-06)
A rapid, simple and highly sensitive reversed-phase high-performance liquid chromatographic method is described for the separation and quantitation of fatty acids in human serum using a very reactive fluorescent labeling reagent, 9-anthryldiazomethane. Quantitative esterification proceeds at room temperature without heat
Walter J Lukiw et al.
The Journal of clinical investigation, 115(10), 2774-2783 (2005-09-10)
Deficiency in docosahexaenoic acid (DHA), a brain-essential omega-3 fatty acid, is associated with cognitive decline. Here we report that, in cytokine-stressed human neural cells, DHA attenuates amyloid-beta (Abeta) secretion, an effect accompanied by the formation of NPD1, a novel, DHA-derived
Matthew J Sharman et al.
Neurobiology of disease, 124, 505-519 (2019-01-06)
Increasingly, evidence is accumulating pointing at a protective role of a healthy diet at decreasing the risk of Alzheimer's disease. To test the effectiveness of nutritional components, the following food-derived compounds: curcumin alone (curcumin), curcumin combined with (-)epigallocatechin-3-gallate (EGCG), docosahexaenoic
Articles
Lipid Induced Insulin Resistance
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Can I use regular tips and vials instead of glass?
1 answer-
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How is shipping temperature determined? And how is it related to the product storage temperature?
1 answer-
Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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How can I determine the shelf life / expiration / retest date of this product?
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If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdfHelpful?
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Is Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid soluble in DMSO? If so, what is the solubility of the product in DMSO?
1 answer-
This product has not been tested for solubility in DMSO. However, various sources state this product can be solubilized in DMSO at a concentration of 100 mM.
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What is the best way to prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid?
1 answer-
D2534 is soluble in chloroform at a concentration of 50 mg/mL. For biological or biochemical applications, chloroform is probably not suitable. Information in our files indicates that the product would be expected to be soluble in 95% ethanol to at least 10 mg/mL.
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Are all of the double bonds in the Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in the cis-configuration?
1 answer-
Yes, this product's double bond configuration is cis.
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After I prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in ethanol, how should it be stored?
1 answer-
The solution in ethanol would be unstable. It is best to make solutions up fresh. If this is not possible, divide the solution into aliquots and layer argon or nitrogen over the solution in each vial. Also, the product may be packaged in ampules, or kept in a vial with a cap plug or vacuum seal and stored at -70 °C. Any antioxidant such as BHT (di-tert-butyl hydroxytoluene) will aid in preventing oxidation of this product. BHT would be one of the better antioxidants to use. It can be used at 0.1% w/w or in the most extreme cases up to 1%. The most important thing to do to prevent oxidation is to exclude oxygen from contacting the product.
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Is Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, a solution? If so, what is the solvent? If not, what is the density?
1 answer-
D2534 is not a solution; it is a neat oil. The density of D2534 is approximately 0.95 g/mL.
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What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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I know that Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, is very prone to oxidation. I would like to study the oxidation in detail. Do you have any references?
1 answer-
A rapid method for studying the oxidation of fatty acids, including linoleic acid, eicosapentaenoic acid and docosahexaenoic acid, has been published. Boyd, L.C., et al., A rapid method for determining the oxidation of n-3 fatty acids. J. Am. Oil Chem. Soc., 69, 325-330 (1992).
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