ChemicalBook > CAS DataBase List > PHORBOL 12-MYRISTATE 13-ACETATE

PHORBOL 12-MYRISTATE 13-ACETATE

Product Name
PHORBOL 12-MYRISTATE 13-ACETATE
CAS No.
16561-29-8
Chemical Name
PHORBOL 12-MYRISTATE 13-ACETATE
Synonyms
TPA;12-O-TETRADECANOYLPHORBOL 13-ACETATE;Recombinant Human Tissue Plasminogen Activator;phorbol ester;factora1;,9aalpha))-;Cocarcinogen A1;Cocarcinogen C3;pma(tumorpromoter);factora1(crotonoil)
CBNumber
CB2376433
Molecular Formula
C36H56O8
Formula Weight
616.83
MOL File
16561-29-8.mol
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PHORBOL 12-MYRISTATE 13-ACETATE Property

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)
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Safety

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.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P1585
Product name
PMA
Purity
foruseinmolecularbiologyapplications,≥99%(HPLC)
Packaging
5MG
Price
$276
Updated
2024/03/01
Sigma-Aldrich
Product number
524400
Product name
Phorbol-12-myristate-13-acetate
Packaging
1mg
Price
$82.8
Updated
2024/03/01
Sigma-Aldrich
Product number
524400
Product name
Phorbol-12-myristate-13-acetate
Packaging
5mg
Price
$208
Updated
2024/03/01
Sigma-Aldrich
Product number
5.00582
Product name
InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem
Packaging
2MG
Price
$111
Updated
2024/03/01
Alfa Aesar
Product number
J63916
Product name
Phorbol 12-myristate 13-acetate, 99+%
Packaging
1mg
Price
$105
Updated
2024/03/01
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PHORBOL 12-MYRISTATE 13-ACETATE Chemical Properties,Usage,Production

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

PHORBOL 12-MYRISTATE 13-ACETATE Preparation Products And Raw materials

Raw materials

Preparation Products

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PHORBOL 12-MYRISTATE 13-ACETATE Suppliers

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View Lastest Price from PHORBOL 12-MYRISTATE 13-ACETATE manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
PHORBOL 12-MYRISTATE 13-ACETATE 16561-29-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-05
Hebei Dangtong Import and export Co LTD
Product
PHORBOL 12-MYRISTATE 13-ACETATE 16561-29-8
Price
US $2150.00-2130.00/gram
Min. Order
20gram
Purity
99%
Supply Ability
100tons
Release date
2023-02-15
Henan Fengda Chemical Co., Ltd
Product
PHORBOL 12-MYRISTATE 13-ACETATE 16561-29-8
Price
US $8.00-1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-03

16561-29-8, PHORBOL 12-MYRISTATE 13-ACETATERelated Search:

1,2-DIOCTANOYL-SN-GLYCEROL Prostratin, PKC activator 1-OLEOYL-2-ACETYL-SN-GLYCEROL (-)-INDOLACTAM V INGENOL 3,20-DIBENZOATE (+)-7-OCTYLINDOLACTAM V FTT PHORBOL 12-MYRISTATE 13-ACETATE PHORBOL 4Α-PHORBOL 12-MYRISTATE 13-ACETATE PHORBOL 13-ACETATE 4A-PHORBOL 12-MYRISTATE 13-ACETATE, 99+%,4-A-PHORBOL 12-MYRISTATE-13-ACETATE NEGA TIVE CONTROL,4ALPHA-PHORBOL 12-MYRISTATE 13-ACETATE PHORBOL-12-MYRISTATE-13-ACETATE, [20-3H(N)] PHORBOL 12-MYRISTATE-13-ACETATE-4-O-METHYL ETHER,PHORBOL 12-MYRISTATE 13-ACETATE 4-O-METHYL ETHER, 4BETA,PHORBOL 12-MYRISTATE-13-ACETATE-4-O- & PHORBOL 16-HYDROXY 12-PALMITATE 13-ACETATE Phorbol 12-myristate 13-acetate diester 12-O-hexadecanoylphorbol-13-acetate PHORBOL-12-MYRISTATE-13-ACETATE = PMA

  • 13-o-acetylphorbol12-myristate
  • 4)benz(1,2-e)azulen-5-one9a-acetate,(+)-ethyl-5h-cyclopropa(
  • 5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,1,1a-beta,1b-alpha,4,4a,7a-beta,7b,
  • 12-O-Tetradecanoyl-Phorbol-13-Acetate(TPA, MPA) 16561-29-8
  • 12-O-tetradecanoyl phorbol-13-acetate (PMA)
  • Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem
  • InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem
  • 4BETA-PHORBOL 12-MYRISTATE 13-ACETATE
  • 4BETA,9ALPHA,12BETA,13ALPHA,20-PENTA-HYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
  • 4ALPHA,9ALPHA,12BETA,13ALPHA,20-PENTAHYDROXYTIGLIA-1,6-DIEN-3-ONE 12BETA-MYRISTATE 13-ACETATE
  • (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 TETRADECANOATE
  • 12-TETRADECANOYL PHORBOL 13-ACETATE
  • 12-O-TETRADECANOYLPHORBOL 13-ACETATE
  • PHORBOL 12-MYRISTATE 13-ACETATE, SYNTHET IC
  • PHORBOL 12-MYRISTATE 13-ACETATE,*MOLECUL AR BIOLOGY
  • PHORBOL 12-MYRISTATE 13-ACETATE FROM &
  • 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-cyclopropa3,4benz1,2-eazulen-9-yl ester
  • 4B-PHORBOL-12-MYRISTATE-13-ACETATE
  • 2-ORTHO-TETRADECANOYL-PHORBOL-13-ACETATE
  • O-TETRADECANOYLPHORBOL-13-ACETATE
  • 12-ORTHO-TETRADECANOYLPHORBOL-13-ACETATE
  • Recombinant Human Tissue Plasminogen Activator
  • 12-O-Tetradecanoylphorbol 13-acetate, PMA, TPA, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
  • Phorbol 12-myristate 13-acetate,99%
  • Phorbol 12-myristate 13-acetate,97%
  • PHORBOL(12-MYRISTOYL-13-ACETYL) ANALYTICAL GRADE
  • Phorbol 12-myristate 13-acetate,12-O-Tetradecanoylphorbol 13-acetate, 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate, PMA, TPA
  • Phorbol 12-Myristate 13-Acetate >99.5%
  • Phorbol-12-Myristate-13-acetate / 12-Tetradecanoyl phorbol-13-acetate, TPA
  • PMA, TPA, Cocarcinogen A1
  • 12-O-TETRADECANOYL PHORBOL-13-ACETATE;COCARCINOGEN A1; COCARCINOGEN C3
  • Cocarcinogen A1
  • Cocarcinogen C3
  • (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 tetradecanoate
  • 12-O-tetradecanoyl phorbol-13-acetate(CAS：16561-29-8)
  • 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
  • PHORBOL 12-MYRISTATE 13-ACETATE, SYN
  • (1AR,1bS,4aR,7aS,7bS,8R,9R,9aS)
  • -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
  • -9a-acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)
  • InSolution? Phorbol-12-myristate-13-acetate
  • PHORBOL 12-MYRISTATE 13-ACETATE
  • PHORBOL (12-MYRISTOYL-13-ACETYL)
  • TPA
  • 8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethy
  • abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetram
  • a-tetramethyl-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,9a-acetate
  • -e)azulen-9-ylester,(1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta
  • factora1
  • factora1(crotonoil)
  • factora1[crotonoil]
  • hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1h-cyclopropa(3,4)benz(1,2
  • myristicacid,9-esterwith1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydr
  • myristicacid,9-esterwith1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4
  • o-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alph
  • pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
  • phorbol12-tetradecanoate13-acetate
  • phorbolacetate,myristate