D5156

Sigma-Aldrich

1,2-Dioctanoyl-sn-glycerol

≥96% (TLC), oil

Synonym(s):
(S)-Glycerol 1,2-dioctanoate, D-α,β-Dicaprylin, 1,2-Dicapryloyl-sn-glycerol, DOG
Empirical Formula (Hill Notation):
C19H36O5
CAS Number:
Molecular Weight:
344.49
Beilstein/REAXYS Number:
1714754
MDL number:
PubChem Substance ID:

assay

≥96% (TLC)

form

oil

color

yellow

solubility

DMSO: soluble

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC

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Biochem/physiol Actions

Cell-permeable, diacylglycerol (DAG) analog, and activator of protein kinase C (PKC). Shown to possess a lower affinity for the α isoform of PKC than for the other isoforms. Mimics the action of tumor-promoting phorbol esters, such as phorbol 12-myristate 13-acetate (PMA). Inhibits slow (L-type) Ca2+ current in rat heart cells independently of PKC activation and also inhibits the cGMP-gated channel in rod outer segments by a phosphorylation-independent mechanism.

Other Notes

Synthetic 1,2-diglyceride of short chain fatty acid.

Caution

Some isomerization to the 1,3-isomer may occur in storage or in solution.

Certificate of Analysis

Certificate of Origin

Inés Fernández-Ulibarri et al.
Molecular biology of the cell, 18(9), 3250-3263 (2007-06-15)
Diacylglycerol is necessary for trans-Golgi network (TGN) to cell surface transport, but its functional relevance in the early secretory pathway is unclear. Although depletion of diacylglycerol did not affect ER-to-Golgi transport, it led to a redistribution of the KDEL receptor...
Weera Piyatheerawong et al.
Journal of chromatography. A, 1068(2), 243-248 (2005-04-16)
A novel HPLC-based method for direct separation of the three isomers of mono-acid diacylglycerols (DAGs), i.e., 1,2-DAG, 2,3-DAG and 1,3-DAG, has been established. The method employs a tandem column system, in which two different columns (a conventional silica gel column...
Johnny Näsman et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 26(42), 10658-10666 (2006-10-20)
We studied the cellular response to orexin type 1 receptor (OX1R) stimulation in differentiated IMR-32 neuroblastoma cells. In vitro differentiation of IMR-32 cells with 5-bromo-2'-deoxyuridine leads to a neuronal phenotype with long neurite extensions and an upregulation of mainly N-type...
S E Gordon et al.
Biophysical journal, 69(2), 409-417 (1995-08-01)
The electrical response to light in retinal rods is mediated by cyclic nucleotide-gated, nonselective cation channels in the outer segment plasma membrane. Although cGMP appears to be the primary light-regulated second messenger, cellular levels of other substances, including Ca2+ and...
Carole A Farah et al.
Molecular and cellular biology, 28(15), 4719-4733 (2008-05-29)
In Aplysia californica, the serotonin-mediated translocation of protein kinase C (PKC) Apl II to neuronal membranes is important for synaptic plasticity. The orthologue of PKC Apl II, PKCepsilon, has been reported to require phosphatidic acid (PA) in conjunction with diacylglycerol...

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