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Docosahexaenoic Acid methyl ester

Names

[ CAS No. ]:
2566-90-7

[ Name ]:
Docosahexaenoic Acid methyl ester

[Synonym ]:
4,7,10,13,16,19-Docosahexaenoic acid, methyl ester, (all-Z)-
fame 22:6n-3
docosa-4c,7c,10c,13c,16c,19c-hexaenoic acid methyl ester
all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester
Methyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
4,7,10,13,16,19-Docosahexaenoic acid, methyl ester, (4Z,7Z,10Z,13Z,16Z,19Z)-
Methyl (4E,7E,10E,13E,16E,19E)-4,7,10,13,16,19-docosahexaenoate
Methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate
DHA methyl ester
Docosahexaenoic acid methyl
Docosa-4c,7c,10c,13c,16c,19c-hexaensaeure-methylester
methyl 4,7,10,13,16,19-docosahexaenoate
4,7,10,13,16,19-Docosahexaenoic acid, methyl ester, (4E,7E,10E,13E,16E,19E)-
all-cis-4,7,10,13,16,19-Docosahexaenoic acid methyl ester solution
Fame 22:6n-3,Methyl all-cis-4,7,10,13,16,19-docosahexenoate,Methyl DHA

Biological Activity

[Description]:

Docosahexaenoic Acid methyl ester is a methylated docosahexaenoic acid analog which can be intercalated into membrane phospholipids without being oxidized or hydrolyzed.

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Neurological Disease

[In Vitro]

Sharp wave (SPW) incidence relative to baseline appears to decrease following Docosahexaenoic Acid methyl ester (DHA-Me) application[1]. There is no generation of a new protein band when bovine serum albumin (BSA) is exposed to the Fe2+ and ascorbic acid (AsA) mixed-function oxidation system in the absence of Docosahexaenoic Acid methyl ester (DHA). However, the high-molecular-weight protein band is observed after only 24 h when BSA is incubated with DHA. Incubation of BSA with 1.0 mM DHA leads to a substantial increase in protein carbonyl content and the addition of oxygen radical scavengers leads to a substantial decrease in protein carbonyl content[2].

[Kinase Assay]

Protein (1 mg/mL) is incubated with Docosahexaenoic Acid methyl ester (DHA) (1.0 mM) in 50 mM HEPES buffer (pH 7.4) containing 0.2% (w/v) of Tween 20 at 37°C. Mannitol, histidine, sodium benzoate, or KI is added at final concentration of 0.5 M, 0.2 M, 0.5 M, or 0.1 M, respectively. Reactive oxygen species are generated by addition of FeSO4 (1 μM) and ascorbic acid (AsA, 20 μM)[2].

[References]

[1]. Taha AY, et al. Selective reduction of excitatory hippocampal sharp waves by docosahexaenoic acid and its methyl ester analog ex-vivo. Brain Res. 2013 Nov 6;1537:9-17.

[2]. Liu W, et al. Formation of high-molecular-weight protein adducts by methyl docosahexaenoate peroxidation products. Biochim Biophys Acta. 2007 Feb;1774(2):258-66.


[Related Small Molecules]

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Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
429.9±24.0 °C at 760 mmHg

[ Molecular Formula ]:
C23H34O2

[ Molecular Weight ]:
342.515

[ Flash Point ]:
103.9±21.2 °C

[ Exact Mass ]:
342.255890

[ PSA ]:
26.30000

[ LogP ]:
7.24

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.505

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
F,N,Xn

[ Risk Phrases ]:
11-67-65-50/53-38

[ Safety Phrases ]:
16-62-61-24/25

[ RIDADR ]:
UN1170 3/PG 2

[ WGK Germany ]:
3

[ Hazard Class ]:
3.0

[ HS Code ]:
29161900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds