P148
4α-Phorbol 12-myristate 13-acetate
solid, ≥95% (TLC)
Synonym(s):
4α-PMA
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About This Item
Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Quality Level
assay
≥95% (TLC)
form
solid
color
white
solubility
H2O: ~2 μM, DMSO: soluble, ethanol: soluble
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)C(C=C(CO)C[C@]3(O)C2C=C(C)C3=O)C4C(C)(C)[C@]14OC(C)=O
InChI
1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34+,35-,36-/m1/s1
InChI key
PHEDXBVPIONUQT-LQLWEASQSA-N
General description
Though having aqueous solubility, it is recommended that this compound first be dissolved in a water miscible organic solvent before dilution to working concentrations in aqueous media.
Biochem/physiol Actions
Negative control for phorbol ester activation of protein kinase C.
Packaging
Sealed glass ampule.
Disclaimer
Photosensitive
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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R A Nichols et al.
Journal of neurochemistry, 48(2), 615-621 (1987-02-01)
Neurotransmitter release from rat brain synaptosomes was measured following pretreatment with various phorbol esters. Ca2+-dependent, evoked neurotransmitter release was increased by phorbol esters that were active in stimulating protein kinase C. Protein kinase C activation was demonstrated by increased incorporation
Gautam Bhave et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(21), 12480-12485 (2003-10-03)
Protein kinase C (PKC) modulates the function of the capsaicin receptor transient receptor potential vanilloid 1 (TRPV1). This modulation manifests as increased current when the channel is activated by capsaicin. In addition, studies have suggested that phosphorylation by PKC might
S M Fischer et al.
Cancer research, 51(3), 850-856 (1991-02-01)
There is substantial evidence that the tumor promoter 4 beta-12-O-tetradecanoylphorbol-13-acetate (TPA) elicits enhanced arachidonic acid release and its metabolism to prostaglandins and lipoxygenase products in many cell types. The goal of this study was to determine whether 4 alpha-12-O-tetradecanoylphorbol-13-acetate (4