Merck
CN
All Photos(1)

Documents

Safety Information

800811C

Avanti

18:1 DG

1-2-dioleoyl-sn-glycerol, chloroform

Sign Into View Organizational & Contract Pricing

Synonym(s):
1-2-di-(9Z-octadecenoyl)-sn-glycerol; DG(18:1(9Z)/18:1(9Z)/0:0); DOG
Empirical Formula (Hill Notation):
C39H72O5
CAS Number:
Molecular Weight:
620.99
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 5 mL (800811C-10mg)
pkg of 1 × 5 mL (800811C-25mg)
pkg of 1 × 8 mL (800811C-200mg)

manufacturer/tradename

Avanti Polar Lipids 800811C

concentration

2 mg/mL (800811C-10mg)
25 mg/mL (800811C-200mg)
5 mg/mL (800811C-25mg)

lipid type

neutral glycerides
neutral lipids

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17+,20-18-/t37-/m0/s1

InChI key

AFSHUZFNMVJNKX-CSWDEDFYSA-N

General description

18:1 DG or 1,2-dioleoyl-sn-glycerol (DOG) comprises a small polar region and is synthesized via phosphatidic acid intermediate.
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.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.

Application

18:1 DG may be used:
  • in the lipid-protein overlay screen assay with Arabidopsis Rho-like GTPases recombinant protein and Arabidopsis plasma membrane H+-ATPase
  • in the preparation of the Golgi-like liposomes
  • in giant unilamellar vesicles (GUVs) preparation

Biochem/physiol Actions

18:1 DG or 1,2-dioleoyl-sn-glycerol (DOG) fails to prevent the late fission events in the Golgi membrane. DOG is used in ferrihaem π–π tetramer aggregate preparation and β-haematin production.

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800811C-10mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800811C-200mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800811C-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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

Regulatory Information

易制毒化学品(2类)
危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Insights into the initial stages of lipid-mediated haemozoin nucleation
Kuter D, et al.
CrystEngComm, 18(27), 5177-5187 (2016)
An improved protein lipid overlay assay for studying lipid-protein interactions
Han X, et al.
Plant methods, 16(1), 1-11 (2020)
Detecting phospholipase activity with the amphipathic lipid packing sensor motif of ArfGAP1
Quartino PY, et al.
Biochemical and Biophysical Research Communications, 505(1), 290-294 (2018)
Conical Lipids in Flat Bilayers Induce Packing Defects Similar to that Induced by Positive Curvature
Vamparys, L
Biophysical Journal, 104, 585-593 (2013)
Activation of ROP6 GTPase by phosphatidylglycerol in Arabidopsis
Han X, et al.
Frontiers in Plant Science, 9, 347-347 (2018)

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