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800814P

Avanti

14:0 DG

1,2-dimyristoyl-sn-glycerol, powder

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

Pricing and availability is not currently available.

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (800814P-10mg)
pkg of 1 × 25 mg (800814P-25mg)

manufacturer/tradename

Avanti Research - A Croda Brand 800814P

lipid type

neutral glycerides
neutral lipids

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

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This Item
800810P840445P800820P
14:0 DG 1,2-dimyristoyl-sn-glycerol, powder

800814P

14:0 DG

10:0 DG 1,2-didecanoyl-sn-glycerol, powder

800810P

10:0 DG

14:0 PG Avanti Research™ - A Croda Brand

840445P

14:0 PG

18:0 DG 1,2-dioctadecanoyl-sn-glycerol, powder

800820P

18:0 DG

form

powder

form

powder

form

powder

form

powder

manufacturer/tradename

Avanti Research - A Croda Brand 800814P

manufacturer/tradename

Avanti Research - A Croda Brand 800810P

manufacturer/tradename

Avanti Research - A Croda Brand

manufacturer/tradename

Avanti Research - A Croda Brand 800820P

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

packaging

pkg of 1 × 10 mg (800814P-10mg), pkg of 1 × 25 mg (800814P-25mg)

packaging

pkg of 1 × 10 mg (with screw cap (800810P-10mg))

packaging

pkg of 1 × 1 g (840445P-1g), pkg of 1 × 200 mg (840445P-200mg), pkg of 1 × 25 mg (840445P-25mg), pkg of 1 × 500 mg (840445P-500mg)

packaging

pkg of 1 × 5 mg (800820P-5mg)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

1,2-dimyristoyl-sn-glycerol (14:0 DG) with small polar headgroup and two fatty acid, is an E coli membrane lipid.[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 may be used:
  • in the reconstitution of dry lipids for thin layer chromatography[6]
  • in lipid nanoparticles for RNA delivery studies[7]
  • as a standard in gas chromatography–mass spectrometry (GC-MS) analysis for the quantification of lipid A diacylglycerols[8]

Biochem/physiol Actions

Diacylglycerol (DAG) displays a flip-flop motion. This movement of DAG is inhibited by membrane protein integrase (mini-MPIase-3).It also forms nonlamellar phase.[1]

Packaging

5 mL Amber Glass Screw Cap Vial (800814P-10mg)
5 mL Amber Glass Screw Cap Vial (800814P-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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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    Imidazoline I1 receptor-induced activation of phosphatidylcholine-specific phospholipase C elicits mitogen-activated protein kinase phosphorylation in PC12 cells
    Zhang J, et al.
    European Journal of Pharmacology, 415(2-3), 117-125 (2001)
    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
    Elisa Callegari et al.
    Molecular therapy. Nucleic acids, 11, 485-493 (2018-06-03)
    Hepatocellular carcinoma (HCC) is the second leading cause of cancer-related death worldwide. Prognosis is poor, and therapeutic options are limited. MicroRNAs (miRNAs) have emerged as potential therapeutic molecules against cancer. Here, we investigated the therapeutic efficacy of miR-199a-3p, an miRNA
    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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