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Key Documents

800819C

Avanti

18:0-22:6 DG

1-stearoyl-2-docosahexaenoyl-sn-glycerol, chloroform

Sinonimo/i:

1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol; DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)

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About This Item

Formula empirica (notazione di Hill):
C43H72O5
Numero CAS:
Peso molecolare:
669.03
Codice UNSPSC:
12352211
NACRES:
NA.25

Saggio

>99% (TLC)

Forma fisica

liquid

Confezionamento

pkg of 1 × 5 mL (800819C-10mg)

Produttore/marchio commerciale

Avanti Research - A Croda Brand 800819C

Concentrazione

2 mg/mL (800819C-10mg)

Tipo di lipide

neutral lipids
neutral glycerides

Condizioni di spedizione

dry ice

Temperatura di conservazione

−20°C

Categorie correlate

Descrizione generale

In biochemical signaling, diacylglycerol (DAG) functions as a second messenger signaling lipid, and is a product of the hydrolysis of the phospholipid PIP2 (phosphatidylinositolbisphosphate) by the enzyme phospholipase C (PLC) (a membrane-bound enzyme) that, through the same reaction, produces inositol trisphosphate (IP3). Although inositol trisphosphate (IP3) diffuses into the cytosol, DAG remains within the plasma membrane due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum, whereas DAG is a physiological activator of protein kinase C (PKC). The production of DAG in the membrane facilitates translocation of PKC from the cytosol to the plasma membrane.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.

Applicazioni

18:0-22:6 DG or 1-stearoyl-2-docosahexaenoyl-sn-glycerol has been used:
  • in the preparation of Golgi-like liposomes
  • to study its effect on conventional protein kinase C (cPKC) and novel protein kinase C (nPKC) isozymes in vitro
  • as a substrate for the measurement of diacylglycerol kinase η1 (DGKη1) activity in vitro

Confezionamento

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800819C-10mg)

Stoccaggio e stabilità

Diacylglycerols are conveniently stored in chloroform solutions in glass vials with PTFE-lined caps at -20°C. Under these conditions acyl migration is minimal. Avoid plastic when handling chloroform solutions.

Altre note

Delivery to cells:
Dry samples of diacylglycerol in chloroform, using a stream of nitrogen. Dissolve the residue in an appropriate volume of ethanol or DMSO, then dilute to the desired aqueous medium.
Effective concentration:
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
Precaution: Since short chain Diacylglycerols mimic effects of the tumor-promoting phorbol diesters in a number of biological systems, extra care should be employed in their handling. Treatment of solutions, vessels and other articles with 1N NaOH before washing or discarding will destroy diacylglycerols.

Note legali

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Pittogrammi

Skull and crossbonesHealth hazard

Avvertenze

Danger

Classi di pericolo

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Organi bersaglio

Central nervous system, Liver,Kidney

Classe di pericolosità dell'acqua (WGK)

WGK 3


Certificati d'analisi (COA)

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Matthew W Bunce et al.
The Journal of biological chemistry, 283(13), 8678-8686 (2008-01-26)
Phosphoinositide signaling pathways regulate numerous processes in eukaryotic cells, including migration, proliferation, and survival. The regulatory lipid phosphatidylinositol 4,5-bisphosphate is synthesized by two distinct classes of phosphatidylinositol phosphate kinases (PIPKs), the type I and II PIPKs. Although numerous physiological functions
Seung-Yeol Park et al.
Nature communications, 10(1), 3409-3409 (2019-08-01)
Studies on vesicle formation by the Coat Protein I (COPI) complex have contributed to a basic understanding of how vesicular transport is initiated. Phosphatidic acid (PA) and diacylglycerol (DAG) have been found previously to be required for the fission stage
Specificity and Mechanism of Protein Kinase C Activation by sn-1,2-diacylglycerols.
Ganong BR, et al.
Proceedings of the National Academy of Sciences of the USA, 83, 1184-1188 (1986)
J G Ebeling et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(3), 815-819 (1985-02-01)
Activation of cellular protein kinase C appears to be involved in the mechanism by which phorbol diesters induce differentiation of human myeloid leukemia cells (HL-60). Protein kinase C is thought to be physiologically activated by diacylglycerol derived from receptor-mediated phosphatidylinositol
R J Davis et al.
The Journal of biological chemistry, 260(3), 1562-1566 (1985-02-10)
The cell-permeable diacylglycerol, sn-1,2-dioctanoylglycerol (DiC8), is shown to mimic the effect of tumor promoting phorbol diesters on epidermal growth factor (EGF) binding and action in intact cells. DiC8 inhibited the binding of [3H]phorbol dibutyrate to A431 cell monolayers indicating that

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