MilliporeSigma
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D2534

Sigma-Aldrich

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

≥98%

Synonym(s):
DHA
Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
Molecular Weight:
328.49
Beilstein:
1715505
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

algae

Quality Level

assay

≥98%

form

liquid

functional group

carboxylic acid

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)

Packaging

25, 100 mg in ampule
1 g in ampule
Sealed ampule.

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.

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

Certificate of Analysis

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Certificate of Origin

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