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

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;PMA (Phorbol 12-myristate 13-acetate);12-O-tetradecanoylphorbol-13-acetate (TPA);Phorbo;factora1;P1585-1MG;,9aalpha))-
CBNumber:
CB2376433
Molecular Formula:
C36H56O8
Molecular Weight:
616.83
MDL Number:
MFCD00036736
MOL File:
16561-29-8.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-17 09:03:53
Product description Number Pack Size Price
PMA foruseinmolecularbiologyapplications,≥99%(HPLC) P1585 5MG $319
Phorbol-12-myristate-13-acetate 524400 1mg $91.2
Phorbol-12-myristate-13-acetate 524400 5mg $229
InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem 5.00582 2MG $122
Phorbol 12-myristate 13-acetate ≥95% 10008014 1mg $43
More product size

PHORBOL 12-MYRISTATE 13-ACETATE 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
SMILES 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
CAS DataBase Reference 16561-29-8(CAS DataBase Reference)
NCI Dictionary of Cancer Terms 12-O-tetradecanoylphorbol-13-acetate; tetradecanoylphorbol acetate
FDA UNII NI40JAQ945
NCI Drug Dictionary tetradecanoylphorbol acetate
EPA Substance Registry System 12-O-Tetradecanoylphorbol 13-acetate (16561-29-8)
UNSPSC Code 12352211
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  Corrosion (GHS05)Skull and Crossbones (GHS06)Health Hazard (GHS08)
GHS05,GHS06,GHS08
Signal word  Danger
Hazard statements  H300+H310+H330-H314-H317-H334-H351
Precautionary statements  P202-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  38-36/37/38
Safety Statements  36/37-26
RIDADR  2928
WGK Germany  3
RTECS  QH4377000
8-10
HazardClass  6.1(a)
PackingGroup  II
HS Code  29153900
Storage Class 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard Classifications Acute Tox. 1 Dermal
Acute Tox. 1 Inhalation
Acute Tox. 2 Oral
Carc. 2
Eye Dam. 1
Resp. Sens. 1
Skin Corr. 1B
Skin Sens. 1
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.
NFPA 704
0
1 0

PHORBOL 12-MYRISTATE 13-ACETATE price More Price(142)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P1585 PMA foruseinmolecularbiologyapplications,≥99%(HPLC) 16561-29-8 5MG $319 2026-04-30 Buy
Sigma-Aldrich 524400 Phorbol-12-myristate-13-acetate 16561-29-8 1mg $91.2 2026-04-30 Buy
Sigma-Aldrich 524400 Phorbol-12-myristate-13-acetate 16561-29-8 5mg $229 2026-04-30 Buy
Sigma-Aldrich 5.00582 InSolution Phorbol-12-myristate-13-acetate - CAS 16561-29-8 - Calbiochem 16561-29-8 2MG $122 2026-04-30 Buy
Cayman Chemical 10008014 Phorbol 12-myristate 13-acetate ≥95% 16561-29-8 1mg $43 2026-04-30 Buy
Product number Packaging Price Buy
P1585 5MG $319 Buy
524400 1mg $91.2 Buy
524400 5mg $229 Buy
5.00582 2MG $122 Buy
10008014 1mg $43 Buy

PHORBOL 12-MYRISTATE 13-ACETATE Chemical Properties,Uses,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] LUCI?LIA SARAIVA . Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay[J]. European journal of pharmacology, 2004, 491 2: Pages 101-110. DOI:10.1016/j.ejphar.2004.03.035
[2] D DOERNER. Protein kinase C-dependent and -independent effects of phorbol esters on hippocampal calcium channel current.[J]. Journal of Neuroscience, 1990, 10 5: 1699-1706.
[3] Merck’s Index, Nachtrag 1930. Verlag von E. Merck, Darmstadt. 14 Seiten[J]. Archiv der Pharmazie, 1930, 268 6: 444-445. DOI:10.1002/ardp.19302680608

17673-25-5
16561-29-8
Synthesis of PHORBOL 12-MYRISTATE 13-ACETATE from PHORBOL

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

Raw materials

Preparation Products

Global( 425)Suppliers
Supplier Tel Email Country ProdList Advantage
Chengdu Biopurify Phytochemicals Ltd.
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18502101150 ft-sales@nature-standard.com CHINA 1923 58
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View Lastest Price from PHORBOL 12-MYRISTATE 13-ACETATE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Phorbol 12-myristate 13-acetate pictures 2026-07-17 Phorbol 12-myristate 13-acetate
16561-29-8
$44.00-129.00 99.96% 10g TargetMol Chemicals Inc.
		PHORBOL 12-MYRISTATE 13-ACETATE pictures 2026-07-09 PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
$1.00-8.00 1kg 99% Henan Fengda Chemical Co., Ltd
PHORBOL 12-MYRISTATE 13-ACETATE pictures 2026-07-01 PHORBOL 12-MYRISTATE 13-ACETATE
16561-29-8
$2130.00-2150.00 20gram 99% 100tons Hebei Dangtong Import and export Co LTD
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, 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 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 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) 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 phorbolmonoacetatemonomyristate phorbolmyristateacetate pma(tumorpromoter) tetradecanoicacid,9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-di tetradecanoylphorbolacetate ,9aalpha))- 1,6,8-beta-tetramethyl-l)-9a-acetate9-myristate
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