Phorbol 12,13-dibutyrate

Base Information

• Chemical Name: Phorbol 12,13-dibutyrate
• CAS No.: 37558-16-0
• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.621
• Hs Code.: 2915601990
• European Community (EC) Number: 636-433-2
• UN Number: 2928
• UNII: 67MX82CL58
• DSSTox Substance ID: DTXSID50958628
• Nikkaji Number: J246.188I
• Wikipedia: Phorbol_12,13-dibutyrate
• Wikidata: Q7187368
• Pharos Ligand ID: 344XFHQTPGKL
• Metabolomics Workbench ID: 50970
• ChEMBL ID: CHEMBL27768
• Mol file: 37558-16-0.mol

Synonyms:12,13-Dibutyrate, Phorbol;Phorbol 12,13 Dibutyrate;Phorbol 12,13-Dibutyrate;Phorbol-12,13-Dibutyrate

Chemical Property of Phorbol 12,13-dibutyrate

Chemical Property:

• Vapor Pressure: 3.72E-18mmHg at 25°C
• Refractive Index: 1.4480 (estimate)
• Boiling Point: 623.4°Cat760mmHg
• PKA: 11.15±0.70(Predicted)
• Flash Point: 199.3°C
• PSA: 130.36000
• Density: 1.27g/cm³
• LogP: 2.63210
• Storage Temp.: −20°C
• Solubility.: H2O: 30 μM
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 504.27231823
• Heavy Atom Count: 36
• Complexity: 1030
• Transport DOT Label: Poison Corrosive

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phorbol 12,13-dibutyrate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)CCC)O)C
• Isomeric SMILES: CCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)CCC)O)C
• Uses: Phorbol 12,13-dibutyrate has been used as a protein kinase C (PKC) activator to study its effects on human organic anion transporter 4 (hOAT4) activity. It has also been used as a PKC activator to analyze its effects on galectin-3 expression and matrix production in HL-1 cells.

Technology Process of Phorbol 12,13-dibutyrate

There total 16 articles about Phorbol 12,13-dibutyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

12,13-bisbutyrate-20-Trt phorbol → phorbol 12,13-dibutyrate (37558-16-0)

Guidance literature:

With perchloric acid; In methanol; at 20 - 25 ℃; for 12h; Inert atmosphere; Darkness;

DOI:10.1016/j.tetlet.2015.01.126

Reference yield: 68.0%

C20H28O6(C4H6O)3 → phorbol 12,13-dibutyrate (37558-16-0)

Guidance literature:

With perchloric acid; In methanol; at 20 ℃; for 48h;

DOI:10.1021/ol990809k

Reference yield: 66.0%

Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (325781-14-4) → 12-epi-phorbol-12,13-dibutyrate (37558-16-0)

Guidance literature:

With perchloric acid; In methanol; at 20 ℃; for 0.75h;

DOI:10.1271/bbb.64.2429

upstream raw materials:

phorbol

phorbol-20-trityl ether

phorbol

Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Refernces

• 1、 Boudreault, Pierre-Luc,Mattler, Jennifer K.,Wender, Paul A.. "Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes". . p. 3423 - 3427. Retrieved 2015.
• 2、 Irie,Nakahara,Ikawa,Tanaka,Nakagawa,Nakamura,Ohigashi,Wender. "Synthesis and tumor-promoting activities of 12-Epi-phorbol-12,13-dibutyrate.". . p. 2429 - 2436. Retrieved 2007/10/03.