1-Stearoyl-2-arachidonoyl-sn-glycerol

Names

[ Name ]:
1-Stearoyl-2-arachidonoyl-sn-glycerol

[Synonym ]:
5,8,11,14-Eicosatetraenoic acid, (1S)-2-hydroxy-1-[[(1-oxooctadecyl)oxy]methyl]ethyl ester, (5Z,8Z,11Z,14Z)-
(1-hydroxy-3-octadecanoyloxypropan-2-yl) icosa-5,8,11,14-tetraenoate
(2S)-1-Hydroxy-3-(stearoyloxy)-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoate
18:0/20:4-DG
1-stearoyl-2-arachidonoylglycerol
2-O-arachidonoyl-1-O-stearoyl-sn-glycerol
5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-[[(1-oxooctadecyl)oxy]methyl]ethyl ester, (5Z,8Z,11Z,14Z)-
(2S)-1-hydroxy-3-(stearoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
1-stearoyl-2-arachidonyl glycerol
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol
MFCD00070361
1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycerol
1-stearoyl-2-arachidonyl-sn-glycerol
1-STEAROYL-2-ARACHIDONOYL-SN-GLYCEROL
1-Hydroxy-3-(stearoyloxy)-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoate
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2]

Biological Activity

[Description]:

1-Stearoyl-2-arachidonoyl-sn-glycerol is a diacylglycerol (DAG) containing polyunsaturated fatty acids. 1-Stearoyl-2-arachidonoyl-sn-glycerol can activate PKC. 1-Stearoyl-2-arachidonoyl-sn-glycerol also can augment nonselective cation channel (NSCC) activity[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Neurological Disease

Signaling Pathways >> TGF-beta/Smad >> PKC

[Target]

PKC[2]

[In Vitro]

1-Stearoyl-2-arachidonoyl-sn-glycerol (0.3-3 μM) augments nonselective cation channel (NSCC) activity in airway smooth muscle cells[1]. 1-Stearoyl-2-arachidonoyl-sn-glycerol (0-5 μM) exerts significantly stimulatory effects on activation of PKCα, PKCδ, PKCγ, PKCε and PKCβI[2].

[References]

[1]. Song T, et, al. Inositol 1,4,5-trisphosphate activates TRPC3 channels to cause extracellular Ca2+ influx in airway smooth muscle cells. Am J Physiol Lung Cell Mol Physiol. 2015 Dec 15;309(12):L1455-66.

[2]. Madani S, et, al. Implication of acyl chain of diacylglycerols in activation of different isoforms of protein kinase C. FASEB J. 2001 Dec;15(14):2595-601.

[3]. Glasmacher S, et, al. Characterization of pepcan-23 as pro-peptide of RVD-hemopressin (pepcan-12) and stability of hemopressins in mice. Adv Biol Regul. 2021 May;80:100808.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
689.2±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₁H₇₂O₅

[ Molecular Weight ]:
645.007

[ Flash Point ]:
190.3±25.0 °C

[ Exact Mass ]:
644.537964

[ PSA ]:
72.83000

[ LogP ]:
15.26

[ Vapour Pressure ]:
0.0±4.9 mmHg at 25°C

[ Index of Refraction ]:
1.488

[ 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)

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Diacylglycerol kinase η1 is a high affinity isozyme for diacylglycerol.

FEBS Lett. 589 , 1272-7, (2015)

Diacylglycerol kinase (DGK) η plays important roles in various patho-physiological events such as oncogenesis. In this study, we performed an enzymological characterization of DGKη splice variant 1 (D...

Melanopsin-expressing amphioxus photoreceptors transduce light via a phospholipase C signaling cascade.

PLoS ONE 7 , e29813, (2012)

Melanopsin, the receptor molecule that underlies light sensitivity in mammalian 'circadian' receptors, is homologous to invertebrate rhodopsins and has been proposed to operate via a similar signaling...

Metabolic fate of plasma membrane diacylglycerols in NIH 3T3 fibroblasts.

J. Biol. Chem. 267(21) , 14783-9, (1992)

We have examined the metabolism of three radiolabeled 1,2-diacylglycerols (DGs) in NIH 3T3 fibroblasts. Since the lipids used are not appreciably taken up by the cells, we used a phosphatidylserine (P...