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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:
Molecular Weight:
645.01
Beilstein:
2198923
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:

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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S Madani et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 15(14), 2595-2601 (2001-12-01)
We synthesized diacylglycerols (DAGs) containing omega-6 or omega-3 polyunsaturated fatty acids [i.e., 1-stearoyl-2-arachidonoyl-sn-glycerol (SAG), 1-stearoyl-2-docosahexaenoyl-sn-glycerol (SDG), and 1-stearoyl-2-eicosapentaenoyl-sn-glycerol (SEG)] and assessed their efficiency on activation of conventional (alpha, beta I, gamma) and novel (epsilon, delta) protein kinase C (PKC). SAG
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
R Zidovetzki et al.
Biochemical pharmacology, 45(1), 183-189 (1993-01-07)
The effects of 1-stearoyl,2-sn-arachidonoylglycerol (SAG) and the antimalarial drug chloroquine on lipid bilayer structure were studied by 2H-NMR spectroscopy. Model lipid systems were established with compositions similar to those of normal human erythrocytes, malaria-infected erythrocytes, or malaria parasite membranes. The
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
M N Hodgkin et al.
The Biochemical journal, 322 ( Pt 2), 529-534 (1997-03-01)
1-Stearoyl-2-arachidonoylglycerol (SAG) kinase was identified in the particulate fraction of pig testes. This activity was enriched by hydroxyapatite and blue dye chromatography. The enzyme was selective for polyunsaturated diradylglycerol species and activity was not modulated by other diradylglycerol species or

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