Isophorbol

Base Information

• Chemical Name: Isophorbol
• CAS No.: 26241-63-4
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439
• European Community (EC) Number: 636-778-9
• Nikkaji Number: J17.049F
• Mol file: 26241-63-4.mol

Synonyms:4-alpha-phorbol;4alpha-phorbol;beta-phorbol;isophorbol;phorbol;phorbol, (1aR-(1aalpha,1bbeta,4aalpha,7aalpha,7balpha,8alpha,9beta,9bbeta))-isomer

Chemical Property of Isophorbol

Chemical Property:

• Vapor Pressure: 1.83E-15mmHg at 25°C
• Boiling Point: 572°C at 760 mmHg
• Flash Point: 313.8°C
• PSA: 118.22000
• Density: 1.415g/cm³
• LogP: -0.06990
• Storage Temp.: −20°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 364.18858861
• Heavy Atom Count: 26
• Complexity: 753

Purity/Quality:

≥98% ^*data from raw suppliers

4alpha-Phorbol ≥98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@@]4(CC(=C3)CO)O)C)O)O)O

Technology Process of Isophorbol

There total 38 articles about Isophorbol 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: 62.0%

Acetic acid (1aS,1bR,4aS,7aR,7bR,8S,9S,9aR)-9-acetoxy-3-acetoxymethyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (19891-05-5) → Phorbol (17673-25-5,26241-63-4,27638-91-1,48211-51-4,123409-56-3)

Guidance literature:

With barium dihydroxide; In methanol;

DOI:10.1021/ja9706256

Reference yield:

C27H38O8 (77573-38-7) → Phorbol (17673-25-5,26241-63-4,27638-91-1,48211-51-4,123409-56-3)

Guidance literature:

Multi-step reaction with 13 steps

1: MnO₂ / CH₂Cl₂

2: H₂ / Pt/C / ethyl acetate / 760 Torr

3: 1.) ArSeCN, (n-Bu)3P, 2.) m-CPBA / 1.) THF, room temp., 2.) CH₂Cl₂, -78 deg C

4: KCN / methanol

5: DMAP / CH₂Cl₂

6: 1.) DIBAH, 2.) DMAP / 1.) toluene, 2.) pyridine, CH₂Cl₂

7: 50 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 0 °C

8: 1.) SOCl₂, propylene oxide, 2.) KOBz, DMAP / 1.) Et₂O, 2.) CH₃CN

9: HClO₄, Montmorillonite clay (K₁₀) / methanol; ethane-1,2-diol

10: 80 percent / SO₃*pyr*Et₃N / dimethylsulfoxide

11: 91 percent / DMAP / acetonitrile

13: 1.) TsOH, 2.) KCN / 1.) MeOH, 2.) MeOH

With tert.-butylhydroperoxide; dmap; potassium cyanide; manganese(IV) oxide; selenium(IV) oxide; thionyl chloride; perchloric acid; pyridine-SO₃ complex; tributylphosphine; Montmorillonite clay (K₁₀); hydrogen; Potassium benzoate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; methyloxirane; platinum on activated charcoal; In methanol; dichloromethane; ethylene glycol; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/ja00206a050

Reference yield:

C27H36O8 (123358-28-1) → Phorbol (17673-25-5,26241-63-4,27638-91-1,48211-51-4,123409-56-3)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Pt/C / ethyl acetate / 760 Torr

2: 1.) ArSeCN, (n-Bu)3P, 2.) m-CPBA / 1.) THF, room temp., 2.) CH₂Cl₂, -78 deg C

3: KCN / methanol

4: DMAP / CH₂Cl₂

5: 1.) DIBAH, 2.) DMAP / 1.) toluene, 2.) pyridine, CH₂Cl₂

6: 50 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 0 °C

7: 1.) SOCl₂, propylene oxide, 2.) KOBz, DMAP / 1.) Et₂O, 2.) CH₃CN

8: HClO₄, Montmorillonite clay (K₁₀) / methanol; ethane-1,2-diol

9: 80 percent / SO₃*pyr*Et₃N / dimethylsulfoxide

10: 91 percent / DMAP / acetonitrile

12: 1.) TsOH, 2.) KCN / 1.) MeOH, 2.) MeOH

With tert.-butylhydroperoxide; dmap; potassium cyanide; selenium(IV) oxide; thionyl chloride; perchloric acid; pyridine-SO₃ complex; tributylphosphine; Montmorillonite clay (K₁₀); hydrogen; Potassium benzoate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; methyloxirane; platinum on activated charcoal; In methanol; dichloromethane; ethylene glycol; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/ja00206a050

upstream raw materials:

C₄₄H₄₈O₉Si

Acetic acid (1aS,1bR,4aS,7aR,7bR,8S,9S,9aR)-9-acetoxy-3-acetoxymethyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

C₂₆H₄₄O₅Si

Downstream raw materials:

4α-Phorbol-20-tritylether

Phenyl-acetic acid (1aR,1bS,4aS,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 ester

13,20-diacetyl-12-phenylacetyl-4α-phorbol

13-acetyl-20-homovanillyl-12-phenylacetyl-4α-phorbol

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