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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Christian Winter et al.
American journal of physiology. Cell physiology, 301(5), C1251-C1261 (2011-08-13)
Urinary acidification in the collecting duct is mediated by the activity of H(+)-ATPases and is stimulated by various factors including angiotensin II and aldosterone. Classically, aldosterone effects are mediated via the mineralocorticoid receptor. Recently, we demonstrated a nongenomic stimulatory effect...
C L Grey et al.
Journal of neuroendocrinology, 23(12), 1273-1287 (2011-09-17)
Ghrelin (GRLN) and its receptor have been identified and characterised in goldfish brain and the pituitary, and recent evidence shows that goldfish (g)GRLN(19) induces both growth hormone (GH) and maturational gonadotrophin (LH) release through an extracellular Ca(2+) -dependent mechanism in...
Shandra A Doran et al.
Canadian journal of physiology and pharmacology, 84(6), 635-646 (2006-08-11)
We examined the roles of Ca2+ and protein kinase C (PKC) in the cilio-excitatory response to serotonin in pedal ciliary cells from Helisoma trivolvis embryos. Serotonin (5-hydroxytryptamine; 5-HT; 100 micromol/L) induced an increase in ciliary beat frequency (CBF) was abolished...
Oded Levanoni et al.
Environmental science & technology, 49(21), 12679-12687 (2015-10-10)
Elevated concentrations of methylmercury (MeHg) in freshwater ecosystems are of major environmental concern in large parts of the northern hemisphere. Beaver ponds have been identified as a potentially important source of MeHg. The role of beavers might be especially pronounced...

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