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Merck
CN

800814C

Avanti

14:0 DG

Avanti Research - A Croda Brand

Synonym(s):

1,2-ditetradecanoyl-sn-glycerol; DG(14:0/14:0/0:0)

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About This Item

Empirical Formula (Hill Notation):
C31H60O5
CAS Number:
Molecular Weight:
512.81
UNSPSC Code:
12352211
NACRES:
NA.25
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Product Name

14:0 DG, 1,2-dimyristoyl-sn-glycerol, chloroform

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 5 mL (800814C-10mg)
pkg of 1 × 5 mL (800814C-25mg)

manufacturer/tradename

Avanti Research - A Croda Brand 800814C

concentration

2 mg/mL (800814C-10mg)
5 mg/mL (800814C-25mg)

lipid type

neutral lipids
neutral glycerides

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1

InChI key

JFBCSFJKETUREV-LJAQVGFWSA-N

General description

1,2-dimyristoyl-sn-glycerol (14:0 DG) is a diacylglycerol (DAG) and is an E coli membrane lipid with small polar headgroup and two fatty acids.
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.

Application

14:0 DG has been used to spike brain extract samples for mass spectroscopy measurements. It may be used in the preparation of liposomes for bovine serum albumin based extraction of different diacylglycerols and as a standard in gas chromatography–mass spectrometry (GC-MS) analysis for the quantification of lipid A diacylglycerols.

Biochem/physiol Actions

Diacylglycerol (DAG) forms nonlamellar phase and displays a flip-flop motion and blocks the integration of membrane protein. This movement of DAG is inhibited by membrane protein integrase (mini-MPIase-3).

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800814C-10mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800814C-25mg)

Preparation Note

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.

Other Notes

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.

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Liver,Kidney

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

Regulatory Information

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Calcium inhibits diacylglycerol uptake by serum albumin
Ahyayauch H, et al.
Biochimica et Biophysica Acta - Biomembranes, 1788(3), 701-707 (2009)
Alteration of membrane physicochemical properties by two factors for membrane protein integration
Nomura K, et al.
Biophysical Journal, 117(1), 99-110 (2019)
Nancy J Phillips et al.
The Journal of biological chemistry, 286(24), 21203-21219 (2011-04-19)
Vibrio fischeri, a bioluminescent marine bacterium, exists in an exclusive symbiotic relationship with the Hawaiian bobtail squid, Euprymna scolopes, whose light organ it colonizes. Previously, it has been shown that the lipopolysaccharide (LPS) or free lipid A of V. fischeri
Quantification of signaling lipids by nano-electrospray ionization tandem mass spectrometry (Nano-ESI MS/MS)
Haag M, et al.
Metabolites, 2(1), 57-76 (2012)
B R Ganong et al.
Proceedings of the National Academy of Sciences of the United States of America, 83(5), 1184-1188 (1986-03-01)
The specificity of protein kinase C activation by sn-1,2-diacylglycerols and analogues was investigated by using a Triton X-100 mixed micellar assay [Hannun, Y. A., Loomis, C. R. & Bell, R. M. (1985) J. Biol. Chem. 260, 10039-10043]. Analogues containing acyl

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