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Phorbol 12-Myristate 13-acetate

$216

  • Brand : BIOFRON

  • Catalogue Number : BD-D1331

  • Specification : 98%(HPLC)

  • CAS number : 16561-29-8

  • Formula : C36H56O8

  • Molecular Weight : 616.83

  • PUBCHEM ID : 27924

  • Volume : 5MG

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Catalogue Number

BD-D1331

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

616.83

Appearance

White crystalline powder

Botanical Source

croton oil Croton tiglium

Structure Type

Diterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CCCCCCCCCCCCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)C)O)C

Synonyms

4β-Phorbol 12-myristate 13-acetate/Tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester/TPA/PMA/12-O-Tetradecanoylphorbol-13-acetate/tetradecanoylphorbol acetate/phorbol 13-acetate 12-myristate/(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-Acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate 12-O-Tetradecanoylphorbol 13-acetate/4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate/(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate Phorbol 12-myristate 13-acetate

IUPAC Name

[(1S,2S,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate

Applications

Phorbol 12-myristate 13-acetate (PMA), a phorbol ester, is a commonly used PKC activator.

Density

1.2±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

208.1±25.0 °C

Boiling Point

698.1±55.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2915390000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:16561-29-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27676154

Abstract

Oncostatin-M (OSM), an IL-6 family cytokine, exhibits varied roles in different patho-physiological conditions. Differential expression of OSM in response to varying stimuli indicates importance of its regulation of expression. The present study illustrated transcriptional induction of osm on treatment with chemical inducer, phorbol-12-myristate-13-acetate (PMA). Following initial hours of PMA treatment, a nuclear protein C/EBP-β binds specifically to the CCAAT consensus sequence at the proximal end of the OSM promoter. Genistein (a specific Tyr phosphorylation inhibitor) leads to the interaction of CHOP (C/EBP Homologous Protein) with C/EBP-β, thus negatively regulating it. Knockdown of C/EBP-β also leads to inhibition of PMA-mediated OSM induction.

KEYWORDS

C/EBP-β; CCAAT consensus sequence; CHOP; Genistein.

Title

Phorbol-12-myristate-13-acetate (PMA) Mediated Transcriptional Regulation of Oncostatin-M

Author

Srimoyee Mukherjee 1 , Sumita Sengupta Bandyopadhyay 2

Publish date

2016 Dec

PMID

29872754

Abstract

Several small molecules have been identified that induce glial cells to synthesize and secrete nerve growth factor (NGF), a critical neurotrophin that supports neuronal growth and survival, and as such show promise in the development of drugs for the chemoprevention of Alzheimer’s disease. To map the signal transduction cascade leading to NGF synthesis and secretion, cultured human glial cells were stimulated by phorbol 12-myristate 13-acetate (PMA), an agonist of Protein Kinase C. Changes in intracellular protein phosphorylation states were evaluated by reverse phase protein microarrays (RPPA), selectively screening over 130 protein endpoints. Of these, 55 proteins showed statistically significant changes in phosphorylation state due to cellular exposure to PMA. A critical signal transduction pathway was identified, and subsequent validation by ELISA and qPCR revealed that the signaling proteins Raf, MEK, ERK, and the signal transduction factor CREB are all essential to the upregulation of NGF gene expression by PMA. Additionally, members of the RSK family of kinases appear to be involved in glial secretion (exocytosis) of the NGF protein. Furthermore, through RPPA, the effects of PMA on apoptosis signaling events and cell proliferation were differentiated from the pathway to NGF upregulation. Overall, this study reveals potential protein targets for the rational design of Alzheimer’s therapeutics.

KEYWORDS

C/EBP-β; CCAAT consensus sequence; CHOP; Genistein.

Title

Induction of Nerve Growth Factor by Phorbol 12-myristate 13-acetate Is Dependent Upon the Mitogen Activated Protein Kinase Pathway

Author

Justin B Davis 1 , Valerie Calvert 1 , Steven Roberts 1 , Sabrina Bracero 1 , Emanuel Petricoin 1 , Robin Couch 1

Publish date

2018 May 14

PMID

25918710

Abstract

Perinatal infections have a negative impact on brain development. However, the underlying mechanisms leading to neurological impairment are not completely understood and reliable models of inflammation are urgently needed. Using phorbol-myristate-acetate as an activator of inflammation, we investigated the effect on the developing rodent brain. Neonatal rats and mice deficient in IL-18 or IRAK-4 were exposed to PMA. Brains were assessed for regulation of pro- and anti-inflammatory cytokines and cell death 24 hrs, 7 and 14 days after treatment. PMA induced an inflammatory response and caused widespread neurodegeneration in the brains of 3- and 7-day-old rats. In contrast, 14-day-old rats were resistant to the neurotoxic effect of PMA. Histological evaluation at the age of 14 and 21 days revealed a destruction of the cortical microstructure with decreased numerical density of neuronal cells. Mice deficient in IL-18 or IRAK-4 were protected against PMA induced brain injury. PMA treatment during a vulnerable period can alter brain development. IL-18 and IRAK-4 appear to be important for the development of PMA induced injury.

Title

Effects of PMA (PHORBOL-12-MYRISTATE-13-ACETATE) on the Developing Rodent Brain

Author

Mark Dzietko 1 , Maria Hahnemann 2 , Oliver Polley 3 , Marco Sifringer 4 , Ursula Felderhoff-Mueser 1 , Christoph Buhrer 3

Publish date

2015