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MedKoo Cat#: 529013 | Name: Phorbol 12-myristate 13-acetate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phorbol 12-myristate 13-acetate is a protein kinase C (PKC) agonist potentially for the treatment of acute myeloid leukemia and cardiac fibrosis. Phorbol 12-myristate 13-acetate induces a rapid loss in TP63 protein and rapid enrichment of HOPX.

Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 529013

Name: Phorbol 12-myristate 13-acetate

CAS#: 16561-29-8

Chemical Formula: C36H56O8

Exact Mass: 616.3975

Molecular Weight: 616.84

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 325.00 2 Weeks
10mg USD 525.00 2 Weeks
25mg USD 1,000.00 2 Weeks
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Related CAS #
No Data
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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#CMC80829
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Phorbol 12-myristate 13-acetate (PMA), a phorbol ester, is a dual SphK and protein kinase C (PKC) activator.
In vitro activity:
A search for factors that regulate Npnt gene expression in osteoblasts revealed that phorbol 12-myristate 13-acetate (PMA), which activates protein kinase C (PKC), had a strong effect to suppress that expression. Research was then conducted to elucidate the signaling pathway responsible for regulation of Npnt gene expression by PMA in osteoblasts. Treatment of MC3T3-E1 cells with PMA suppressed cell differentiation and Npnt gene expression. Effects were noted at a low concentration of PMA, and were time- and dose-dependent. Reference: Sci Rep. 2021 Oct 13;11(1):20360. https://pubmed.ncbi.nlm.nih.gov/34645824/
In vivo activity:
For inducing skin inflammation, topical PMA (phorbol 12-myristate 13-acetate) administration (10 μg) was done on the mice ear for three consecutive days, which efficiently replicated the symptoms similar to human psoriasis in mice model. PMA treated ears evidently had hyperkeratosis (epidermal thickening), parakeratosis (nucleated keratinocyte accumulates in the uppermost stratum corneum skin layer, and a greater neutrophilic intra-epidermal inflammatory cell infiltrate) (Figure 5F). Reference: Int J Mol Sci. 2020 Dec 4;21(23):9261. https://pubmed.ncbi.nlm.nih.gov/33291656/
Solvent mg/mL mM comments
Solubility
DMSO 87.2 141.41
Ethanol 100.0 162.12
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:
1. Kinoshita M, Yamada A, Sasa K, Ikezaki K, Shirota T, Kamijo R. Phorbol-12-myristate 13-acetate inhibits Nephronectin gene expression via Protein kinase C alpha and c-Jun/c-Fos transcription factors. Sci Rep. 2021 Oct 13;11(1):20360. doi: 10.1038/s41598-021-00034-x. PMID: 34645824; PMCID: PMC8514542. 2. Chang YY, Lu CW, Jean WH, Shieh JS, Lin TY. Phorbol myristate acetate induces differentiation of THP-1 cells in a nitric oxide-dependent manner. Nitric Oxide. 2021 May 1;109-110:33-41. doi: 10.1016/j.niox.2021.02.002. Epub 2021 Mar 2. PMID: 33667621. 3. Chang SN, Dey DK, Oh ST, Kong WH, Cho KH, Al-Olayan EM, Hwang BS, Kang SC, Park JG. Phorbol 12-Myristate 13-Acetate Induced Toxicity Study and the Role of Tangeretin in Abrogating HIF-1α-NF-κB Crosstalk In Vitro and In Vivo. Int J Mol Sci. 2020 Dec 4;21(23):9261. doi: 10.3390/ijms21239261. PMID: 33291656; PMCID: PMC7729754. 4. Kwon OK, Lee JW, Xuezhen X, Harmalkar DS, Song JG, Park JW, Hwang D, Min JH, Kim JH, Han HK, Jeong HG, Oh SR, Ahn KS, Lee K. DK-1108 exerts anti-inflammatory activity against phorbol 12-myristate 13-acetate-induced inflammation and protective effect against OVA-induced allergic asthma. Biomed Pharmacother. 2020 Dec;132:110950. doi: 10.1016/j.biopha.2020.110950. Epub 2020 Nov 3. PMID: 33254440.
In vitro protocol:
1. Kinoshita M, Yamada A, Sasa K, Ikezaki K, Shirota T, Kamijo R. Phorbol-12-myristate 13-acetate inhibits Nephronectin gene expression via Protein kinase C alpha and c-Jun/c-Fos transcription factors. Sci Rep. 2021 Oct 13;11(1):20360. doi: 10.1038/s41598-021-00034-x. PMID: 34645824; PMCID: PMC8514542. 2. Chang YY, Lu CW, Jean WH, Shieh JS, Lin TY. Phorbol myristate acetate induces differentiation of THP-1 cells in a nitric oxide-dependent manner. Nitric Oxide. 2021 May 1;109-110:33-41. doi: 10.1016/j.niox.2021.02.002. Epub 2021 Mar 2. PMID: 33667621.
In vivo protocol:
1. Chang SN, Dey DK, Oh ST, Kong WH, Cho KH, Al-Olayan EM, Hwang BS, Kang SC, Park JG. Phorbol 12-Myristate 13-Acetate Induced Toxicity Study and the Role of Tangeretin in Abrogating HIF-1α-NF-κB Crosstalk In Vitro and In Vivo. Int J Mol Sci. 2020 Dec 4;21(23):9261. doi: 10.3390/ijms21239261. PMID: 33291656; PMCID: PMC7729754. 2. Kwon OK, Lee JW, Xuezhen X, Harmalkar DS, Song JG, Park JW, Hwang D, Min JH, Kim JH, Han HK, Jeong HG, Oh SR, Ahn KS, Lee K. DK-1108 exerts anti-inflammatory activity against phorbol 12-myristate 13-acetate-induced inflammation and protective effect against OVA-induced allergic asthma. Biomed Pharmacother. 2020 Dec;132:110950. doi: 10.1016/j.biopha.2020.110950. Epub 2020 Nov 3. PMID: 33254440.
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SLN-00535

SLN-00535