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800815 | 16:0-18:1 DG

Name: 16:0-18:1 DG
Brand: Avanti Research
SKU: 800815O-200mg
Price: 120.6 USD
Availability: InStock

1-palmitoyl-2-oleoyl-sn-glycerol

Oil

Size	SKU	Packaging	Price
10mg	800815O-10mg 800815O-10mg	1 x 10mg	$120.60 120.6
25mg	800815O-25mg 800815O-25mg	1 x 25mg	$213.25 213.25
200mg	800815O-200mg 800815O-200mg	2 x 100mg	$588.00 588

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Chloroform

	Size	SKU	Packaging	Price
	10mg	800815C-10mg 800815C-10mg	1 x 10mg 2mg/mL 5mL	$120.60 120.6
	25mg	800815C-25mg 800815C-25mg	1 x 25mg 5mg/mL 5mL	$213.25 213.25

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Info

16:0-18:1 DG

1-palmitoyl-2-oleoyl-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

Yes

Light Sensitive

Molecular Formula

C₃₇H₇₀O₅

Percent Composition

C 74.70%, H 11.86%, O 13.45%

Purity

>99%

Stability

1 Year

Storage Temperature

-20°C

CAS Number

29541-66-0
CAS Registry Number is a Registered Trademark of the American Chemical Society

Formula Weight

594.949

Exact Mass

594.522

Synonyms

1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol
DG(16:0/18:1(9Z)/0:0)

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References

Eum JY, Lee JC, Yi SS, Kim IY, Seong JK, Moon MH. Aging-related lipidomic changes in mouse serum, kidney, and heart by nanoflow ultrahigh-performance liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2020 Jan 3:460849. doi: 10.1016/j.chroma.2020.460849. Epub ahead of print. PMID: 31928769.

PubMed ID: 31928769

Murakami C, Hoshino F, Sakai H, Hayashi Y, Yamashita A, Sakane F. Diacylglycerol kinase δ and sphingomyelin synthase-related protein functionally interact via their sterile α motif domains. J Biol Chem. 2020 Jan 24:jbc.RA119.012369. doi: 10.1074/jbc.RA119.012369. Epub ahead of print. PMID: 31980461.

PubMed ID: 31980461

Campbell JM, Tate G, Scott JS. The use of warfarin in pregnancy complicated by circulating lupus anticoagulant; a technique for monitoring. Eur J Obstet Gynecol Reprod Biol. 1988 Sep;29(1):27-32.

PubMed ID: 31478204

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

Zhang X, Barraza KM, Upton KT, Beauchamp JL. Subtle Changes in Lipid Environment Have Profound Effects on Membrane Oxidation Chemistry. J Am Chem Soc. 2018 Nov 21. doi: 10.1021/jacs.8b08610. [Epub ahead of print]

PubMed ID: 30461271

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.

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

Bockelmann S, Mina JGM, Korneev S, Hassan DG, Mueller D, Hilderink A, Vlieg HC, Raijmakers R, Heck AJR, Haberkant P, Holthuis JCM. A search for ceramide binding proteins using bifunctional lipid analogs yields CERT-related protein StarD7. J Lipid Res. 2018 Jan 17. pii: jlr.M082354. doi: 10.1194/jlr.M082354. [Epub ahead of print]

PubMed ID: 29343537

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800815 | 16:0-18:1 DG

1-palmitoyl-2-oleoyl-sn-glycerol