Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

D2534

Sigma-Aldrich

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

≥98%

Synonym(s):

DHA

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
6217-54-5
Molecular Weight:
328.49
Beilstein:
1715505
MDL number:
MFCD00065722
UNSPSC Code:
12352211
PubChem Substance ID:
24893696
NACRES:
NA.25

biological source

algae

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

D2534-1G:
D2534-VAR:
D2534-500MG:
D2534-25MG:
D2534-100MG:
D2534-BULK:
D2534-10MG:

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Ana M Torres-Guzman et al.
Arthritis research & therapy, 16(2), R64-R64 (2014-03-13)
Clinical and preclinical studies have shown that supplementation with ω-3 polyunsaturated fatty acids (ω-3 PUFAs) reduce joint destruction and inflammation present in rheumatoid arthritis (RA). However, the effects of individual ω-3 PUFAs on chronic arthritic pain have not been evaluated
Eduardo Luiz Moreira et al.
Toxicological sciences : an official journal of the Society of Toxicology, 130(2), 373-382 (2012-08-21)
Methylmercury (MeHg) is an environmental pollutant that biomagnifies throughout the aquatic food chain, thus representing a toxicological concern for humans subsiding on fish for their dietary intake. Although the developing brain is considered the critical target organ of MeHg toxicity
View All Related Papers

Articles

Omega-3 Fatty Acids and Heart Disease

The potential for the prevention and treatment of cardiovascular disease through increased dietary intake of omega-3 (w-3) fish oils is not a recent scientific discovery.

Lipid Induced Insulin Resistance

Lipid Induced Insulin Resistance

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service