D5156
1,2-Dioctanoyl-sn-glycerol
≥96% (TLC), oil
Synonym(s):
(S)-Glycerol 1,2-dioctanoate, 1,2-Dicapryloyl-sn-glycerol, D-α,β-Dicaprylin, DOG
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About This Item
Empirical Formula (Hill Notation):
C19H36O5
CAS Number:
Molecular Weight:
344.49
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
1714754
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
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.
Disclaimer
Some isomerization to the 1,3-isomer may occur in storage or in solution.
Storage Class
12 - Non Combustible Liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Regulatory Information
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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
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
C Bijleveld et al.
Biochemical and biophysical research communications, 151(1), 193-200 (1988-02-29)
Exogenous 1-oleoyl-2-acetylglycerol (OAG) is known to mimic the action of tumour-promoting phorbol esters in various cell types. However, in isolated rat hepatocytes OAG depressed the rate of de novo fatty acid synthesis and the activity of the key enzyme acetyl-CoA