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S6389

Sigma-Aldrich

1-Stearoyl-2-arachidonoyl-sn-glycerol

~98%, suitable for stimulation of protein kinase C derived from liver cells, liquid

Synonym(s):

1-Octadecanoyl-2-([cis,cis,cis,cis]-5,8,11,14-eicosatetraenoyl)-sn-glycerol, 2-Arachidonoyl-1-stearoyl-sn-glycerol

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About This Item

Empirical Formula (Hill Notation):
C41H72O5
CAS Number:
65914-84-3
Molecular Weight:
645.01
Beilstein:
2198923
MDL number:
MFCD00070361
UNSPSC Code:
41106305
PubChem Substance ID:
24899699

Assay

~98%

form

liquid

impurities

1,3-isomer, trace

solubility

chloroform: 20 mg/ml

suitability

suitable for stimulation of protein kinase C derived from liver cells

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI

1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-

InChI key

NSXLMTYRMFVYNT-LGHBDAFPSA-N

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Application

1-Stearoyl-2-arachidonoyl-sn-glycerol was used to study Ca+2 signaling.5,6

Biochem/physiol Actions

1-Stearoyl-2-arachidonoyl-sn-glycerol is a diacyl glycerol (DAG) that allosterically activates PKC and other proteins that affect cell growth, development, survival, apoptosis, carcinogenesis and metastasis.3 It activates transient receptor potential channels 3 and 6 that regulates the intracellular free calcium levels.4

Packaging

Sealed ampule

Caution

This material may isomerize during storage.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
070M5201
128K5201
077K5200
106H8485
079H5207

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J O Hindenes et al.
The Journal of biological chemistry, 275(10), 6857-6867 (2000-03-04)
sn-1,2-diacylglycerol (DAG), a key intermediate in lipid metabolism, activates protein kinase C and is a fusogen. Phosphoinositides, the main sources of DAG in cell signaling, contain mostly stearoyl and arachidonoyl in the sn-1 and -2 positions, respectively. The polymorphic behavior
J Florin-Christensen et al.
The Journal of biological chemistry, 267(21), 14783-14789 (1992-07-25)
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 (PS)-based liposome fusion system to rapidly associate the lipid species
Elizabeth M Deacon et al.
Journal of cell science, 115(Pt 5), 983-989 (2002-03-01)
Protein kinase C (PKC) is a family of 11 isoenzymes that are differentially involved in the regulation of cell proliferation. PKC-betaII, a mitotic lamin kinase, has been shown previously to translocate to the nucleus at G(2)/M and this was coupled
M Fatholahi et al.
Archives of biochemistry and biophysics, 374(2), 395-401 (2000-02-10)
The changes in total Mg were compared with changes in cytosolic free Mg(2+) during metabolic stimulation of collagenase-dispersed rat cardiac myocytes or Langendorff-perfused rat hearts. In myocytes the addition of agents leading to cAMP increase or protein kinase C activation
Chihiro Hisatsune et al.
The Journal of biological chemistry, 280(12), 11723-11730 (2005-01-08)
Stimulation of various cell surface receptors leads to the production of inositol 1,4,5-trisphosphate (IP3) and diacylglycerol (DAG) through phospholipase C (PLC) activation, and the IP3 and DAG in turn trigger Ca2+ release through IP3 receptors and protein kinase C activation
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