800811 | 18:1 DG

1-2-dioleoyl-sn-glycerol


Oil

Size SKU Packaging Price
10mg 800811O-10mg 800811O-10mg 1 x 10mg $87.20
25mg 800811O-25mg 800811O-25mg 1 x 25mg $154.25
200mg 800811O-200mg 800811O-200mg 2 x 100mg $424.00
500mg 800811O-500mg 800811O-500mg 5 x 100mg $835.00

Chloroform

Size SKU Packaging Price
10mg 800811C-10mg 800811C-10mg 1 x 10mg 2mg/mL 5mL $87.20
25mg 800811C-25mg 800811C-25mg 1 x 25mg 5mg/mL 5mL $154.25
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18:1 DG

18:1 DG

1-2-dioleoyl-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.
Hygroscopic
Yes
Light Sensitive
No
Molecular Formula
C39H72O5
Percent Composition
C 75.43%, H 11.69%, O 12.88%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
24529-88-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
620.986
Exact Mass
620.538
Synonyms
<p>1-2-di-(9Z-octadecenoyl)-sn-glycerol</p> <p>DG(18:1(9Z)/18:1(9Z)/0:0)</p> <p>DOG</p>

Zhou H, Wei Z, Wang S, Yao D, Zhang R, Ma C. Structural and Functional Analysis of the CAPS SNARE-Binding Domain Required for SNARE Complex Formation and Exocytosis. Cell Rep. 2019 Mar 19;26(12):3347-3359.e6. doi: 10.1016/j.celrep.2019.02.064.

PubMed ID: 30893606

Gao S, Wan Y, Li W, Huang C. Visualized Networking of Co-Regulated Lipids in Human Blood Based on High-Throughput Screening Data: Implications for Exposure Assessment. Environ Sci Technol. 2019 Mar 5;53(5):2862-2872. doi: 10.1021/acs.est.8b06289. Epub 2019 Feb 21.

PubMed ID: 30739451

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PubMed ID: 30675774

Brandt C, McFie PJ, Vu H, Chumala P, Katselis GS, Stone SJ. Identification of calnexin as a diacylglycerol acyltransferase-2 interacting protein. PLoS One. 2019 Jan 7;14(1):e0210396. doi: 10.1371/journal.pone.0210396. eCollection 2019.

PubMed ID: 30615684

Mattern-Schain SI, Fisher RK, West PC, Grimsley LB, Harris TM, Grandas OH, Best MD, Mountain DJH. Cell mimetic liposomal nanocarriers for tailored delivery of vascular therapeutics. Chem Phys Lipids. 2019 Jan;218:149-157. doi: 10.1016/j.chemphyslip.2018.12.009. Epub 2018 Dec 21.

PubMed ID: 30582896

Wang S, Li Y, Gong J, Ye S, Yang X, Zhang R, Ma C. Munc18 and Munc13 serve as a functional template to orchestrate neuronal SNARE complex assembly. Nat Commun. 2019 Jan 8;10(1):69. doi: 10.1038/s41467-018-08028-6.

PubMed ID: 30622273

Gao S, Wan Y, Li W, Huang C. Visualized Networking of Co-Regulated Lipids in Human Blood Based on High-Throughput Screening Data: Implications for Exposure Assessment. Environ Sci Technol. 2019 Feb 21. doi: 10.1021/acs.est.8b06289. [Epub ahead of print]

PubMed ID: 30739451

Thomas LL, van der Vegt SA, Fromme JC. A Steric Gating Mechanism Dictates the Substrate Specificity of a Rab-GEF. Dev Cell. 2019 Jan 7;48(1):100-114.e9. doi: 10.1016/j.devcel.2018.11.013. Epub 2018 Dec 6.

PubMed ID: 30528786

Forest A, Ruiz M, Bouchard B, Boucher G, Gingras O, Daneault C, Robillard Frayne I, Rhainds D, Consortium TI, Genetics Consortium TNI, Tardif JC, Rioux JD, Des Rosiers C. A Comprehensive and Reproducible Untargeted Lipidomic Workflow Using LC-QTOF Validated for Human Plasma Analysis. J Proteome Res. 2018 Sep 26. doi: 10.1021/acs.jproteome.8b00270. [Epub ahead of print]

PubMed ID: 30256116

Vamparys, L., R. Gautier, S. Vanni, W.F. Bennett, D.P. Tieleman, B. Antonny, C. Etchebest, and P.F. Fuchs. (2013). Conical Lipids in Flat Bilayers Induce Packing Defects Similar to that Induced by Positive Curvature. Biophys J 104:585-93. [PubMed]

PubMed ID: 23442909

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