Phorbol 12-myristate 13-acetate
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Hodoodo CAT#: H529013

CAS#: 16561-29-8

Description: Phorbol 12-myristate 13-acetate is a protein kinase C (PKC) agonist potentially for the treatment of acute myeloid leukemia and cardiac fibrosis.


Chemical Structure

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Phorbol 12-myristate 13-acetate
CAS# 16561-29-8

Theoretical Analysis

Hodoodo Cat#: H529013
Name: Phorbol 12-myristate 13-acetate
CAS#: 16561-29-8
Chemical Formula: C36H56O8
Exact Mass: 616.40
Molecular Weight: 616.836
Elemental Analysis: Chemical Formula: C36H56O8 Exact Mass: 616.3975 Molecular Weight: 616.8360 Elemental Analysis: C, 70.10; H, 9.15; O, 20.75

Price and Availability

Size Price Availability Quantity
5mg USD 295 2 Weeks
10mg USD 495 2 Weeks
25mg USD 950 2 Weeks
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Synonym: NSC-262244; PD-616; RP-323; NSC262244; PD616; RP323; NSC 262244; PD 616; RP 323; PMA

IUPAC/Chemical Name: (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

InChi Key: PHEDXBVPIONUQT-RGYGYFBISA-N

InChi Code: InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

SMILES Code: CCCCCCCCCCCCCC(O[C@]1([H])[C@@]([C@@]2(O)[C@@]([C@]([C@@]13OC(C)=O)([H])C3(C)C)([H])C=C(CO)C[C@@]4(O)[C@@]2([H])C=C(C4=O)C)([H])C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 616.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Li YH, Bi HC, Huang L, Jin J, Zhong GP, Zhou XN, Huang M. Phorbol 12-myristate 13-acetate inhibits P-glycoprotein-mediated efflux of digoxin in MDCKII-MDR1 and Caco-2 cell monolayer models. Acta Pharmacol Sin. 2014 Feb;35(2):283-91. doi: 10.1038/aps.2013.157. PubMed PMID: 24362330; PubMed Central PMCID: PMC4651225.

2: Wang YP, Wang P, Dong L, Chen H, Wu YQ, Li HW, Li M. Relaxin inhibit cardiac fibrosis induced by phorbol 12-myristate 13-acetate. Biomed Environ Sci. 2014 Feb;27(2):138-41. doi: 10.3967/bes2014.030. PubMed PMID: 24625407.

3: Choi YJ, Lee YH, Lee ST. Galangin and kaempferol suppress phorbol-12-myristate-13-acetate-induced matrix metalloproteinase-9 expression in human fibrosarcoma HT-1080 cells. Mol Cells. 2015;38(2):151-5. doi: 10.14348/molcells.2015.2229. PubMed PMID: 25518925; PubMed Central PMCID: PMC4332032.

4: Song YS, Kim MS, Lee DH, Oh DK, Yoon DY. 15-Hydroxyeicosatetraenoic Acid Inhibits Phorbol-12-Myristate-13-Acetate-Induced MUC5AC Expression in NCI-H292 Respiratory Epithelial Cells. J Microbiol Biotechnol. 2015 May;25(5):589-97. PubMed PMID: 25649981.

5: Song JK, Lee CH, Hwang SM, Joo BS, Lee SY, Jung JS. Effect of phorbol 12-myristate 13-acetate on the differentiation of adipose-derived stromal cells from different subcutaneous adipose tissue depots. Korean J Physiol Pharmacol. 2014 Aug;18(4):289-96. doi: 10.4196/kjpp.2014.18.4.289. PubMed PMID: 25177160; PubMed Central PMCID: PMC4146630.

6: Nishiura H, Yamanegi K, Kawabe M, Kato-Kogoe N, Yamada N, Nakasho K. Annexin A3 plays a role in cytoplasmic calcium oscillation by extracellular calcium in the human promyelocytic leukemia HL-60 cells differentiated by phorbol-12-myristate-13-acetate. Exp Mol Pathol. 2014 Oct;97(2):241-6. doi: 10.1016/j.yexmp.2014.07.010. PubMed PMID: 25036403.

7: Li Y, Bi H, Zhong G, Huang L, Li G, Xia Y, Chen X, Huang M. Effect of phorbol 12-myristate 13-acetate on function and gene expression of P-glycoprotein in adriamycin-resistant K562/ADM cells. Pharmacology. 2013;92(3-4):121-30. doi: 10.1159/000353774. PubMed PMID: 24008321.

8: Monzen S, Takimura K, Kashiwakura I, Hosokawa Y. Acute promyelocytic leukemia mutated to radioresistance suppressed monocyte lineage differentiation by phorbol 12-myristate 13-acetate. Leuk Res. 2013 Sep;37(9):1162-9. doi: 10.1016/j.leukres.2013.04.027. PubMed PMID: 23773897.

9: Olofinsae SA, Ibeh BO, Ahluwalia J. Increased oxygen consumption observed in phorbol 12-myristate 13-acetate stimulated human cultured promonocytic U937 cell lines treated with calcitriol and retinoic acid. Asian Pac J Trop Med. 2014 Sep;7S1:S272-7. doi: 10.1016/S1995-7645(14)60245-5. PubMed PMID: 25312135.

10: Waheed Roomi M, Kalinovsky T, Rath M, Niedzwiecki A. Failure of matrix metalloproteinase-9 dimer induction by phorbol 12-myristate 13-acetate in normal human cell lines. Oncol Lett. 2015 Jun;9(6):2871-2873. PubMed PMID: 26137162; PubMed Central PMCID: PMC4473710.

11: Mukherjee S, Sengupta Bandyopadhyay S. Phorbol-12-myristate-13-acetate (PMA) mediated transcriptional regulation of Oncostatin-M. Cytokine. 2016 Dec;88:209-213. doi: 10.1016/j.cyto.2016.09.006. PubMed PMID: 27676154.

12: Hirose K, Monzen S, Sato H, Sato M, Aoki M, Hatayama Y, Kawaguchi H, Narita Y, Takai Y, Kashiwakura I. Megakaryocytic differentiation in human chronic myelogenous leukemia K562 cells induced by ionizing radiation in combination with phorbol 12-myristate 13-acetate. J Radiat Res. 2013 May;54(3):438-46. doi: 10.1093/jrr/rrs125. PubMed PMID: 23263730; PubMed Central PMCID: PMC3650750.

13: Murao S, Gemmell MA, Callaham MF, Anderson NL, Huberman E. Control of macrophage cell differentiation in human promyelocytic HL-60 leukemia cells by 1,25-dihydroxyvitamin D3 and phorbol-12-myristate-13-acetate. Cancer Res. 1983 Oct;43(10):4989-96. PubMed PMID: 6576856.

14: White JR, Huang CK, Hill JM Jr, Naccache PH, Becker EL, Sha'afi RI. Effect of phorbol 12-myristate 13-acetate and its analogue 4 alpha-phorbol 12,13-didecanoate on protein phosphorylation and lysosomal enzyme release in rabbit neutrophils. J Biol Chem. 1984 Jul 10;259(13):8605-11. PubMed PMID: 6429145.

15: Kim EC, Lee MJ, Shin SY, Seol GH, Han SH, Yee J, Kim C, Min SS. Phorbol 12-Myristate 13-Acetate Enhances Long-Term Potentiation in the Hippocampus through Activation of Protein Kinase Cδ and ε. Korean J Physiol Pharmacol. 2013 Feb;17(1):51-6. doi: 10.4196/kjpp.2013.17.1.51. PubMed PMID: 23440225; PubMed Central PMCID: PMC3579105.

16: Dunphy WG, Delclos KB, Blumberg PM. Characterization of specific binding of [3H]phorbol 12,13-dibutyrate and [3H]phorbol 12-myristate 13-acetate to mouse brain. Cancer Res. 1980 Oct;40(10):3635-41. PubMed PMID: 7438048.

17: Xu H, Ni P, Chen C, Yao Y, Zhao X, Qian G, Fan X, Ge S. SP1 suppresses phorbol 12-myristate 13-acetate induced up-regulation of human regucalcin expression in liver cancer cells. Mol Cell Biochem. 2011 Sep;355(1-2):9-15. doi: 10.1007/s11010-011-0833-2. PubMed PMID: 21526343.

18: Qin MB, Huang JA, Liu SQ, Tang GD, Jiang HX. Inhibition of SPHK1 suppresses phorbol 12-myristate 13-acetate-induced metastatic phenotype in colorectal cancer HT-29 cells. Oncol Res. 2011;19(12):573-82. PubMed PMID: 22812190.

19: Tijburg LB, Houweling M, Geelen JH, van Golde LM. Stimulation of phosphatidylethanolamine synthesis in isolated rat hepatocytes by phorbol 12-myristate 13-acetate. Biochim Biophys Acta. 1987 Nov 21;922(2):184-90. PubMed PMID: 2823905.

20: Tada T, Aki K, Oboshi W, Kawazoe K, Yasui T, Hosoi E. Evaluation of effects of various drugs on platelet functions using phorbol 12-myristate 13-acetate-induced megakaryocytic human erythroid leukemia cells. Drug Des Devel Ther. 2016 Sep 26;10:3099-3107. Erratum in: Drug Des Devel Ther. 2017 Feb 08;11:371. PubMed PMID: 27713620; PubMed Central PMCID: PMC5045028.