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P148

Sigma-Aldrich

4α-Phorbol 12-myristate 13-acetate

solid, ≥95% (TLC)

Synonym(s):

4α-PMA

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1 MG
CHF 254.00

About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
Molecular Weight:
616.83
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

CHF 254.00


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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.

Caution

Photosensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
Shirley A Cotton et al.
Kidney international, 61(1), 61-67 (2002-01-12)
Significant variability exists in the outcome of renal parenchymal inflammation following urinary tract infection (UTI) in childhood as some children experience renal parenchymal scarring (RPS) while others do not scar. Since TGF-beta1 is pro-fibrotic, we examined the role of this
B L Van Duuren et al.
Cancer research, 39(7 Pt 1), 2644-2646 (1979-07-01)
4a alpha-Phorbol-9,9a-didecanoate, 4a alpha-phorbol-9-myristate-9a-acetate, and phorbol-9-myristate-9a-acetate-3-aldehyde were tested for skin tumor-promoting activity by using 7,12-dimethylbenz(a)anthracene as the initiating agent. There were 30 female ICR/Ha mice/group, and tests were continued for 434 to 461 days. 4a alpha-Phorbol-9,9a-didecanoate and 4a alpha-phorbol-9-myristate-9a-acetate were
Izabela Woclawek-Potocka et al.
Prostaglandins & other lipid mediators, 79(3-4), 287-297 (2006-05-02)
Corpus luteum (CL) is a reproductive gland that plays a crucial endocrine role in the regulation of the estrous cycle, fertility, and pregnancy in cattle. The main function of CL is secretion of progesterone (P4), an important hormone for establishment
Feng Xu et al.
British journal of pharmacology, 140(2), 413-421 (2003-09-13)
1. We investigated whether protein kinase C (PKC) activation stimulates Ca2+ entry in HEK 293 cells transfected with human TRPV4 cDNA and loaded with fura-2. 2. Phorbol 12-myristate 13-acetate (PMA), a PKC-activating phorbol ester, increased the intracellular Ca2+ concentration ([Ca2+]i)

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