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MedKoo Cat#: 561551 | Name: Phorbol
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Description:

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

Phorbol is a plant-derived diterpene that protmotes tumor growth through the activation of protein kinase C.

Chemical Structure

Phorbol
Phorbol
CAS#17673-25-5

Theoretical Analysis

MedKoo Cat#: 561551

Name: Phorbol

CAS#: 17673-25-5

Chemical Formula: C20H28O6

Exact Mass: 364.1886

Molecular Weight: 364.44

Elemental Analysis: C, 65.92; H, 7.74; O, 26.34

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
Phorbol;
IUPAC/Chemical Name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one
InChi Key
QGVLYPPODPLXMB-UBTYZVCOSA-N
InChi Code
InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
SMILES Code
O=C1C(C)=C[C@@]2([H])[C@]3(O)[C@@]([C@@](C4(C)C)([H])[C@@]4(O)[C@H](O)[C@H]3C)([H])C=C(CO)C[C@]12O
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
Instruction
View handling instruction
Biological target:
Phorbol is a highly toxic diterpene, whose esters have important biological properties.
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
DMF 30.0 82.32
DMSO 50.7 139.03
PBS (pH 7.2) 1.0 2.74
Water 20.0 54.88
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 364.44 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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