PRODIGIOSIN

Base Information

• Chemical Name: PRODIGIOSIN
• CAS No.: 82-89-3
• Molecular Formula: C20H25 N3 O
• Molecular Weight: 323.438
• Hs Code.: 3204151000
• Mol file: 82-89-3.mol

Synonyms:2,2'-Bipyrrole,4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]- (7CI,8CI);2-Methyl-3-amyl-6-methoxyprodigiosene; Prodigiosin; Prodigiosine

Chemical Property of PRODIGIOSIN

Chemical Property:

• Melting Point: 151-152°
• Boiling Point: 542.4oC at 760 mmHg
• PKA: 17.09±0.50(Predicted)
• Flash Point: 281.8oC
• PSA: 53.17000
• Density: 1.12g/cm3
• LogP: 4.77610
• Storage Temp.: -20C

Purity/Quality:

99%, ^*data from raw suppliers

Prodigiosin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Prodigiosin is an intensely red, pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumour cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β. Prodigiosin is an intensely red pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumor cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β. Prodigiosin is a naturally occurring pigment which occurs as a product of Serratia marcescens. Pink colored pigment.

Technology Process of PRODIGIOSIN

There total 11 articles about PRODIGIOSIN 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: 59.0%

2-methyl-3-pentyl-1H-pyrrole (18320-91-7) + 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (10476-41-2) → 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole (82-89-3)

Guidance literature:

hydrogenchloride; In methanol; at 25 ℃; for 12h;

DOI:10.1016/S0040-4039(00)95451-0

Reference yield:

→ prodigiosine (82-89-3,47371-61-9)

Guidance literature:

4-Methoxy-2,2'-bipyrrol-5-carboxaldehyd, 2-Methyl-3-pentylpyrrol/HCl/MeOH;

DOI:10.1021/ja00863a026 DOI:10.1021/ja01505a056

Reference yield:

4-methoxy-5-(methoxycarbonyl)-2,2'-bipyrrole (112373-36-1) → 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole (82-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / hydrazine / 4 h / 25 °C

2: 97 percent / pyridine / 0.25 h / 25 °C

3: 34 percent / Na₂CO₃ / ethane-1,2-diol / 0.08 h / 170 °C

4: 2.) concd. HCl / 1.) methanol, 100 deg C, 5 min, 2.) methanol, 25 deg C, 30 min

With pyridine; hydrogenchloride; sodium carbonate; hydrazine; In ethylene glycol;

DOI:10.1021/jo00242a013

upstream raw materials:

2-methyl-3-pentyl-1H-pyrrole

4-methoxy-2,2'-bipyrrole-5-carboxaldehyde

ethyl 5-methyl-4-pentanoyl-1H-pyrrole-2-carboxylate

4-methoxy-5-(methoxycarbonyl)-2,2'-bipyrrole

Refernces

• 1、 -. "Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases". . . Retrieved 2008/06/13.
• 2、 -. "Pyrrolydenemethyl-derivatives and process for their preparation". . . Retrieved 2008/06/13.