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P4888

Sigma-Aldrich

4α-Phorbol

powder

Synonym(s):

4α,9α,12β,13α,20-pentahydroxytiglia-1,6-dien-3-one, 4α-PHR, Isophorbol

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About This Item

Empirical Formula (Hill Notation):
C20H28O6
CAS Number:
26241-63-4
Molecular Weight:
364.43
MDL number:
MFCD00036738
UNSPSC Code:
12352200
PubChem Substance ID:
24898565

form

powder

color

white

storage temp.

−20°C

SMILES string

C[C@@H]1[C@@H](O)[C@]2(O)[C@H]([C@@H]3C=C(CO)C[C@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C

InChI

1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18+,19-,20-/m1/s1

InChI key

QGVLYPPODPLXMB-FYYCTCHMSA-N

Application

Phorbol that is not biologically active; can be used as a negative control

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SLBF4325V
SLBF3994V
SLBF3996V
071M1806V
100M1170

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Vijay Lyall et al.
Journal of neurophysiology, 102(3), 1591-1605 (2009-06-26)
The regulation of the benzamil (Bz)-insensitive salt taste receptor was investigated by intracellular Ca2+ ([Ca2+]i), protein kinase C (PKC), and the Ca2+-dependent serine-threonine phosphatase, calcineurin (PP2B), by monitoring chorda tympani taste nerve responses to 0.1 M NaCl solutions containing Bz
Emad Afrasiabi et al.
Molecular and cellular endocrinology, 292(1-2), 26-35 (2008-06-11)
Phorbol 12-myristate 13-acetate (PMA) is known to affect a variety of cellular processes, including cell proliferation, differentiation, and migration. PMA has been shown to promote antiproliferative and antimigratory effects in many types of cancer cells. Our findings show that PMA
Lankupalle D Jayanthi et al.
Molecular pharmacology, 67(6), 2077-2087 (2005-03-19)
The serotonin transporter (SERT) regulates 5-hydroxytryptamine (serotonin) (5-HT) neurotransmission and is a high-affinity target for antidepressants and psychostimulants. In the present study, we investigated the mechanisms that contribute to a previously unidentified biphasic regulation of endogenous SERTs expressed in the
R W Moore et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 134(3), 291-302 (2003-03-20)
In attempts to identify antibodies for Bursal Anti-Steroidogenic Peptide (BASP), rabbit serum was observed to reduce phorbol ester-stimulated chicken B-lymphocyte proliferation comparable to BASP. These experiments investigated the effects of IgG on B-lymphocyte proliferation. In Experiment 1, 3% rabbit serum
Rui Wang et al.
Journal of Asian natural products research, 15(5), 502-506 (2013-04-23)
The phytochemical investigation of the flower buds of Daphne genkwa yielded four highly oxygenated tigliane diterpene esters (1-4), including two new phorbol derivatives, 12-O-(2'E,4'E-decadienoyl)-7-oxo-5-ene-phorbol-13-acetate (1) and 12-O-neodecanoyl-7-oxo-5-ene-phorbol-13-acetate (2). The molecular structures of the isolated compounds were elucidated on the basis
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