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D7821

Sigma-Aldrich

dPPA

≥98% (HPLC)

Synonym(s):

12-Deoxyphorbol 13-phenylacetate 20-acetate, DOPPA

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About This Item

Empirical Formula (Hill Notation):
C30H36O7
CAS Number:
54662-30-5
Molecular Weight:
508.60
MDL number:
MFCD01741294
UNSPSC Code:
12352200
PubChem Substance ID:
329798788
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

oil

color

colorless to light yellow

storage temp.

−20°C

SMILES string

CC(C1=O)=C[C@]2([H])[C@]1(O)CC(COC(C)=O)=C[C@]3([H])[C@]2(O)[C@H](C)C[C@]4(OC(CC5=CC=CC=C5)=O)[C@H]3C4(C)C

InChI

1S/C30H36O7/c1-17-11-23-28(34,26(17)33)15-21(16-36-19(3)31)12-22-25-27(4,5)29(25,14-18(2)30(22,23)35)37-24(32)13-20-9-7-6-8-10-20/h6-12,18,22-23,25,34-35H,13-16H2,1-5H3/t18-,22+,23-,25-,28-,29+,30-/m1/s1

InChI key

MEDVHSNRBPAIPU-XMOZQXTISA-N

Application

dPPA/phorbol ester 12-deoxyphorbol 13-phenylacetate 20-acetate (DOPPA) may be used as a potent activator of PKC-β:
  • to treat transfected HT-22 cells to promote phosphorylation of p66Shc
  • to treat HT-22 and B12 cells to study its effects on cell viability
  • to treat neurons and measure primary cortical neurons using the 2,5-diphenyl-2H-tetrazolium bromide (MTT) assay

Biochem/physiol Actions

dPPA is a phorbol ester that selectively activates the β isotype of PKC. It is approximately 100-fold more potent for PKC-β than the α, γ or δ isotypes. PKC family members each have specific functions, but PKC-β and δ appear to share similar expression profiles, and both are involved in regulating apoptosis and B cell activation, thus dPPA is a useful tool in determining PKCβ specific signaling events.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
076M4722V
101M4728V

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Inhibition of histamine-induced acid secretion in rat isolated gastric mucosa by esters of phorbol and 12-deoxyphorbol.
J B Pearce et al.
The Journal of pharmacy and pharmacology, 33(11), 737-738 (1981-11-01)
T J Williams et al.
Inflammation, 5(1), 29-36 (1981-03-01)
The effects of proinflammatory phorbol and 12-deoxyphorbol esters were determined on blood flow changes and plasma exudation in rabbit skin. Blood flow changes were measured by means of 133Xe washout over that in control-treated sites, while plasma exudation was measured
David C Wright et al.
American journal of physiology. Endocrinology and metabolism, 287(2), E305-E309 (2004-04-01)
Recent evidence has shown that activation of lipid-sensitive protein kinase C (PKC) isoforms leads to skeletal muscle insulin resistance. However, earlier studies demonstrated that phorbol esters increase glucose transport in skeletal muscle. The purpose of the present study was to
Brian T Hawkins et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 30(9), 1593-1597 (2010-07-16)
Blood-brain barrier (BBB) P-glycoprotein activity is rapidly reduced by vascular endothelial growth factor (VEGF) acting via Src and by tumor necrosis factor-alpha acting via protein kinase C (PKC)beta1. To probe underlying mechanism(s), we developed an in vivo, immunoblot-based proteinase K
E M Williamson et al.
Acta pharmacologica et toxicologica, 48(1), 47-52 (1981-01-01)
The pro-inflammatory tigliane esters 12-deoxyphorbolphenylacetate (12-DOPPA) and 12-deoxyphorbolphenylacetate-20-acetate (12-DOPPAA) at a dose of 0.1 microgram induced erythema in the mouse ear. Observations of ear redness were made both two and four hours after application. Indomethacin was only partly successful as
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