P148

4α-Phorbol 12-myristate 13-acetate

Name: 4α-Phorbol 12-myristate 13-acetate
Brand: SIGMA
Price: 306 USD

solid, ≥95% (TLC)

Synonym(s):

4α-PMA

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P148-1MG

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About This Item

Empirical Formula (Hill Notation):

C₃₆H₅₆O₈

CAS Number:

63597-44-4

Molecular Weight:

616.83

MDL number:

MFCD00153860

UNSPSC Code:

12352211

PubChem Substance ID:

24898203

NACRES:

NA.77

Key Documents

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Quality Level

100

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

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Show Differences

1 of 4

This Item	P8139	P8014	P1269
Sigma-Aldrich P148 4α-Phorbol 12-myristate 13-acetate	Sigma-Aldrich P8139 Phorbol 12-myristate 13-acetate	Sigma-Aldrich P8014 4α-Phorbol 12,13-didecanoate	Sigma-Aldrich P1269 Phorbol 12,13-dibutyrate
assay ≥95% (TLC)	assay ≥99% (TLC)	assay -	assay ≥98% (TLC)
form solid	form film or powder	form solid	form powder
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
solubility H₂O: ~2 μM, ethanol: soluble, DMSO: soluble	solubility DMSO: soluble, ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.)	solubility DMSO: soluble, ethanol: soluble, methanol: soluble	solubility H₂O: 30 μM, DMSO: soluble, acetone: soluble, ethanol: soluble
color white	color -	color white	color clear light yellow, film

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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4 Beta- and 4 alpha-12-O-tetradecanoylphorbol-13-acetate elicit arachidonate release from epidermal cells through different mechanisms.

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

Role of TGF-beta1 in renal parenchymal scarring following childhood urinary tract infection.

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

Protein kinase C phosphorylation sensitizes but does not activate the capsaicin receptor transient receptor potential vanilloid 1 (TRPV1).

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

Phorbol ester enhancement of neurotransmitter release from rat brain synaptosomes.

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

Phorbol-12-myristate 13-acetate acting through protein kinase Cepsilon induces translocator protein (18-kDa) TSPO gene expression.

Amani Batarseh et al.

Biochemistry, 47(48), 12886-12899 (2008-11-04)

Translocator protein (TSPO) is an 18-kDa cholesterol-binding protein that is expressed at high levels in steroid synthesizing and several cancer cells where it is involved in steroidogenesis and cell proliferation, respectively. The factors regulating Tspo expression are unknown. We analyzed

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