PHORBOL 12-MYRISTATE 13-ACETATE Chemical Properties

Melting point:

65-79oC

Boiling point:

571.87°C (rough estimate)

Density 

1.17±0.1 g/cm3 (20 ºC 760 Torr)

refractive index 

1.4900 (estimate)

storage temp. 

-20°C

solubility 

DMSO: DMSO solutions can be stored dark at −20°C for at least six months.soluble

form 

Fine Crystalline Powder

pka

11.19±0.70(Predicted)

color 

Off-white to light yellow

Water Solubility 

Very soluble in methanol, soluble in DMSO, chloroform, ethanol or acetone, ether, ethyl acetate, DMF or acetonitrile. Insoluble in water.

Sensitive 

Light Sensitive

BRN 

2407201

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

InChIKey

PHEDXBVPIONUQT-RGYGYFBISA-N

CAS DataBase Reference

16561-29-8(CAS DataBase Reference)

EPA Substance Registry System

12-O-Tetradecanoylphorbol 13-acetate (16561-29-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38-36/37/38

Safety Statements 

36/37-26

RIDADR 

2928

WGK Germany 

3

RTECS 

QH4377000

F 

8-10

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29153900

Hazardous Substances Data

16561-29-8(Hazardous Substances Data)

Toxicity

Diesters of phorbol, particularly 12-O-tetradecanoylphorbol 13-acetate, also known as phorbol myristate acetate, have been identified as the potent, highly lipophilic tumor-promoting components in croton oil. They are potent promoters of skin tumors in vivo and have been shown to transform cultured fibroblasts and embryonic cells previously exposed to polycyclic aromatic hydrocarbon carcinogens in vitro. The structure of phorbol, the parent alcohol is shown below. Phorbol esters also have important effects on leukocytes and on the immune system of the intact animal. There appears to be a specific receptor for phorbol esters on T cells, a finding that may account for the selective toxicity of phorbol esters for T cells. The mechanism of tumor promotion by phorbol esters is still largely unknown, but findings suggest an initial cell membrane interaction (often with stimulation of second messenger synthesis and increased protein kinase activity), with subsequent effects on nuclear regulatory events.

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

PHORBOL 12-MYRISTATE 13-ACETATE Usage And Synthesis

Description

Phorbol 12-myristate-13-acetate (16561-29-8) activates protein kinase C (10-100 ng/ml)1. May display PKC-independent effects in various cell types2. Warning: Phorbol 12-myristate-13-acetate is a skin irritant. Avoid contact with this compound.

Chemical Properties

white to off-white solid

Uses

4β-Phorbol 12-Myristate 13-Acetate is used in the activation of certain pyruvate kinases as well as protein kinases.

Definition

ChEBI: Phorbol 13-acetate 12-myristate is a phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types. It has a role as a protein kinase C agonist, an antineoplastic agent, a reactive oxygen species generator, a plant metabolite, a mitogen, a carcinogenic agent and an apoptosis inducer. It is an acetate ester, a tetradecanoate ester, a diester, a tertiary alpha-hydroxy ketone and a phorbol ester.

General Description

White crystals.

Air & Water Reactions

Practically water insoluble.

Reactivity Profile

PHORBOL 12-MYRISTATE 13-ACETATE is sensitive to acids and alkalis. .

Fire Hazard

Flash point data for PHORBOL 12-MYRISTATE 13-ACETATE are not available; however, PHORBOL 12-MYRISTATE 13-ACETATE is probably combustible.

Biological Activity

Extensively used phorbol ester activator of protein kinase C; tumor promoter. Binds to PKC with a K i value of 2.6 nM as measured by displacement of [ 3 H]phorbol 12,13-dibutyrate binding in rat cortex synaptosomal membranes.

Biochem/physiol Actions

Cell permeable: yes

target

PKC | AP-1

storage

-20°C (protect from light)

References

1) Saraiva et al. (2004), Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay; Eur. J. Pharmacol., 491 101 2) Doerner et al. (1990), Protein kinase C-dependent and independent effects of phorbol esters on hippocampal calcium channel current; J. Neurosci., 10 1699 3) Merck Index 14:7332

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