PHORBOL 12-MYRISTATE 13-ACETATE

Synonym(s):PMA;TPA;12-O-Tetradecanoylphorbol 13-acetate;12-O-Tetradecanoyl-phorbol-13-acetate, PMA, TPA;4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate

CAS NO.：16561-29-8
Empirical Formula: C36H56O8
Molecular Weight: 616.83
MDL number: MFCD00036736
EINECS: 605-413-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 20:33:22

PHORBOL 12-MYRISTATE 13-ACETATE Structural

What is PHORBOL 12-MYRISTATE 13-ACETATE?

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

The Uses of PHORBOL 12-MYRISTATE 13-ACETATE

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

What are the applications of Application

PMA is a reversible and highly potent protein kinase C (PKC) activator in vitro and in vivo at nM concentrations.

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

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

Properties of PHORBOL 12-MYRISTATE 13-ACETATE

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.
CAS DataBase Reference	16561-29-8(CAS DataBase Reference)
EPA Substance Registry System	12-O-Tetradecanoylphorbol 13-acetate (16561-29-8)

Safety information for PHORBOL 12-MYRISTATE 13-ACETATE

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08
GHS Hazard Statements	H314:Skin corrosion/irritation H317:Sensitisation, Skin H334:Sensitisation, respiratory H351:Carcinogenicity
Precautionary Statement Codes	P202:Do not handle until all safety precautions have been read and understood. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.