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D2534

Sigma-Aldrich

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

biological source

algae

Quality Level

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.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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