Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

800814C

Avanti

14:0 DG

1,2-dimyristoyl-sn-glycerol, chloroform

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

Select a Size

All Photos(1)

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C31H60O5
CAS Number:
60562-16-5
Molecular Weight:
512.81
UNSPSC Code:
12352211
NACRES:
NA.25

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.[1]
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.[2][3][4][5]
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.[6] It may be used in the preparation of liposomes for bovine serum albumin based extraction of different diacylglycerols[7] and as a standard in gas chromatography–mass spectrometry (GC-MS) analysis for the quantification of lipid A diacylglycerols.[8]

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).[1]

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)

Storage and Stability

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
GHS06,GHS08

signalword

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

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

wgk_germany

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service