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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
054H8470
054H84702

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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
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
Virginie Aires et al.
Biochimie, 89(8), 926-937 (2007-05-29)
We synthesized a diacylglycerol (DAG)-containing arachidonic acid, i.e., 1-stearoyl-2-arachidonyl-sn-glycerol (SAG), and studied its implication in the modulation of canonical transient receptor potential sub-type 6 (TRPC6) channels in stably-transfected HEK-293 cells. SAG induced the influx of Ca(2+), and also of other
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
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