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800812 | 12:0 DG

1,2-dilauroyl-sn-glycerol

12:0 DG

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12:0 DG

1,2-dilauroyl-sn-glycerol

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. (See References)
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
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.
Storage:
Diacylglycerols are conveniently stored in chloroform solutions in glass vials with teflon-lined caps at -20°C. Under these conditions acyl migration is minimal. Avoid plastic when handling chloroform solutions.
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.
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C27H52O5
Percent Composition
C 71.01%, H 11.48%, O 17.52%
Purity
<99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
60562-15-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
456.699
Exact Mass
456.381
Synonyms
1,2-didodecanoyl-sn-glycerol
DG(12:0/12:0/0:0)
110611
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References

Yang L, Nie H, Zhao F, Song S, Meng Y, Bai Y, Liu H. A novel online two-dimensional supercritical fluid chromatography/reversed phase liquid chromatography-mass spectrometry method for lipid profiling. Anal Bioanal Chem. 2020 Jan 4:10.1007/s00216-019-02242-x. doi: 10.1007/s00216-019-02242-x. Epub ahead of print. PMID: 31901960.

 PubMed ID: 31901960

Boretti FS, Burla B, Deuel J, Gao L, Wenk MR, Liesegang A, Sieber-Ruckstuhl NS. Serum lipidome analysis of healthy beagle dogs receiving different diets. Metabolomics. 2019 Dec 3;16(1):1. doi: 10.1007/s11306-019-1621-3. PMID: 31797205; PMCID: PMC6890591.

 PubMed ID: 31797205

Sun Y, Saito K, Saito Y. Lipid Profile Characterization and Lipoprotein Comparison of Extracellular Vesicles from Human Plasma and Serum. Metabolites. 2019 Nov 1;9(11). pii: E259. doi: 10.3390/metabo9110259.

 PubMed ID: 31683897

Yan B, Zou Z, Chu H, Chan G, Tsang JO, Lai PM, Yuan S, Yip CC, Yin F, Kao RY, Sze KH, Lau SK, Chan JF, Yuen KY. Lipidomic Profiling Reveals Significant Perturbations of Intracellular Lipid Homeostasis in Enterovirus-Infected Cells. Int J Mol Sci. 2019 Nov 26;20(23). pii: E5952. doi: 10.3390/ijms20235952.

 PubMed ID: 31779252

Dinesh Kumar Barupal, Sili Fan, Benjamin Wancewicz, Tomas Cajka, Michael Sa, Megan R. Showalter, Rebecca Baillie, Jessica D. Tenenbaum, Gregory Louie, Alzheimer’s Disease Neuroimaging Initiative, Alzheimer’s Disease Metabolomics Consortium, Rima Kaddurah-Daouk & Oliver Fiehn. Generation and quality control of lipidomics data for the alzheimer’s disease neuroimaging initiative cohort. Scientific Data volume 5, Article number: 180263 (2018).

Ebeling, J.G., Vandenbark, G.R., Kuhn, L., Ganong, B., Bell, R.M. & Niedel, J.E. (1985) Diacylglycerols and Phorbol Diesters Induce Leukemic Cell Differentiation via a Common Mechanism. Proc. Natl. Acad. Sci. USA 82:815-819.

Davis, R.J., Ganong, B.R., Bell, R.M. & Czech, M.P. (1985) sn-1,2-dioctanoylglycerol: a Cell Permeable Diacylglycerol That Mimics Phorbol Diester Action on the Epidermal Growth Factor Receptor and Mitogenesis. J. Biol. Chem. 260:1562-1566.

 PubMed ID: 2981862

Lapetina, E.G., Reep, B., Ganong, B.R. & Bell, R.M. (1985) Exogenous sn-1,2-diacylglycerols Containing Saturated Fatty Acids Functions as Bioregulators of Protein Kinase C in Human Platelets. J. Biol. Chem. 260:1358-1361.

Ganong, B.R., Loomis, C.R., Hannun, Y.A. & Bell, R.M. (1986) Specificity and Mechanism of Protein Kinase C Activation by sn-1,2-diacylglycerols. Proc. Natl. Acad. Sci. USA 83:1184-1188.

 PubMed ID: 3456578
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