37338-80-0

Basic information

• Product Name: orellanine
• Synonyms: orellanine;2,2'-Bi[pyridine-3,4-diol]1,1'-dioxide;2-(3,4-Dihydroxy-1-oxidopyridin-1-ium-2-yl)-3,4-dihydroxypyridin-1-ium-1-olate;[2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide;JEWWXPOUSBVQKG-UHFFFAOYSA-N
• CAS NO: 37338-80-0
• Molecular Formula: C₁₀H₈N₂O₆
• Molecular Weight: 252.17
• Mol File: 37338-80-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 834.615 °C at 760 mmHg
• Flash Point: 458.558 °C
• Appearance: /
• Density: 1.777 g/cm³
• CAS DataBase Reference: orellanine(CAS DataBase Reference)
• NIST Chemistry Reference: orellanine(37338-80-0)
• EPA Substance Registry System: orellanine(37338-80-0)

Safety Data

• Hazardous Substances Data: 37338-80-0(Hazardous Substances Data)

Usage

General Description

Orellanine is a toxic and potentially deadly chemical compound found in certain species of mushrooms, particularly the Cortinarius genus. It is a nephrotoxin, meaning it specifically targets the kidneys, and can cause renal failure and other severe health complications if ingested. Orellanine poisoning can occur if the mushrooms containing the compound are mistakenly eaten, and symptoms of poisoning may not appear until several days after ingestion, making it difficult to diagnose and treat. There is currently no known antidote for orellanine poisoning, and the best course of action is to seek immediate medical attention if poisoning is suspected. Due to its toxicity, it is important for foragers and consumers of wild mushrooms to be knowledgeable about the potential presence of orellanine in certain species and to exercise caution when harvesting and consuming wild mushrooms.

Synthetic route

orelline (72016-31-0) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
With dihydrogen peroxide for 8h; Ambient temperature;	87%
for 336h; Irradiation; isomerisation also without irradiation;

tetra-O-methylorellanine (101664-54-4) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
With hydrogen bromide; acetic acid for 5h; Heating;	77%
With hydrogen bromide at 120℃; for 5h;	60%
With hydrogen bromide at 120℃;	60%
With hydrogen bromide In acetic acid for 4h;	30%

3,3',4,4'-tetramethoxy-2,2'-bipyridine (101664-55-5) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: m-chloroperbenzoic acid 2: m-chloroperbenzoic acid 3: 60 percent / 48percent HBr / 120 °C View Scheme
Multi-step reaction with 2 steps 1: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 2: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 2: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: 41 percent / Ac2O, H2O2 2: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-bromo-3,4-dimethoxy pyridine (104819-52-5) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C 2: m-chloroperbenzoic acid 3: m-chloroperbenzoic acid 4: 60 percent / 48percent HBr / 120 °C View Scheme
Multi-step reaction with 3 steps 1: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 2: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 3: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

2-bromo-3,4-dimethoxy pyridine-N-oxide (105011-83-4) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: phosphorus tribromide 2: 87 percent / NiCl2, P(Ph)3, Zn / dimethylformamide / 50 °C 3: m-chloroperbenzoic acid 4: m-chloroperbenzoic acid 5: 60 percent / 48percent HBr / 120 °C View Scheme
Multi-step reaction with 4 steps 1: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 2: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 3: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 4: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

3,4,3',4'-Tetramethoxy-[2,2']bipyridinyl 1-oxide (112516-35-5) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: m-chloroperbenzoic acid 2: 60 percent / 48percent HBr / 120 °C View Scheme

4-methoxypyridin-3-amine (33631-09-3) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 80 percent / Br2, conc. HCl / 1 h 3: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C 4: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C 5: 92 percent / Na / 0.25 h / Heating 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

2-chloro-3-fluoropyridine (17282-04-1) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 7 steps 1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 83 percent / Na / methanol / 72 h / Ambient temperature 4: 80 percent / PCl3 / CHCl3 / 2 h / Heating 5: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 6: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 7: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 7 steps 1: 54 percent / acetic anhydride, 30percent H2O2 2: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 3: Ambient temperature 4: PCl3 5: 25 percent / dimethylformamide / 4 h / 50 °C 6: 41 percent / Ac2O, H2O2 7: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-Chlor-3-fluorpyridin-1-oxid (85386-94-3) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 83 percent / Na / methanol / 72 h / Ambient temperature 3: 80 percent / PCl3 / CHCl3 / 2 h / Heating 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 2: Ambient temperature 3: PCl3 4: 25 percent / dimethylformamide / 4 h / 50 °C 5: 41 percent / Ac2O, H2O2 6: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-chloro-3,4-dimethoxypyridine (101664-59-9) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 2: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 3: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 25 percent / dimethylformamide / 4 h / 50 °C 2: 41 percent / Ac2O, H2O2 3: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-Chlor-3,4-dimethoxypyridin-1-oxid (101664-58-8) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PCl3 / CHCl3 / 2 h / Heating 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: PCl3 2: 25 percent / dimethylformamide / 4 h / 50 °C 3: 41 percent / Ac2O, H2O2 4: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-Chlor-3-fluor-4-nitropyridin-1-oxid (101664-56-6) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 83 percent / Na / methanol / 72 h / Ambient temperature 2: 80 percent / PCl3 / CHCl3 / 2 h / Heating 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme
Multi-step reaction with 5 steps 1: Ambient temperature 2: PCl3 3: 25 percent / dimethylformamide / 4 h / 50 °C 4: 41 percent / Ac2O, H2O2 5: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-bromo-3-fluoro-4-methoxypyridine (109613-98-1) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C 2: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C 3: 92 percent / Na / 0.25 h / Heating 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

2-bromo-4-methoxy-pyridin-3-amine (109613-97-0) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 5 steps 2: 42 percent / NiCl2*6H2O/(C6H5)3P, Zn / 4 h / 50 °C 3: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C 4: 92 percent / Na / 0.25 h / Heating 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

3,3'-Difluor-4,4'-dimethoxy-2,2'-bipyridin (109613-99-2) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 27 percent / 30percent H2O2, (CH3CO)2O / 14 h / 100 °C 2: 92 percent / Na / 0.25 h / Heating 3: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

3,3'-Difluor-4,4'-dimethoxy-<2,2'-bipyridin>-1,1'-dioxid (109613-94-7) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / Na / 0.25 h / Heating 2: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

3-HYDROXYPYRIDINE (109-00-2) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 9 steps 1: 35 percent / Br2, 10percent aq. NaOH / 24 h 2: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h 3: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 4: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 5: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 6: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 7: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 8: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 9: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

3-hydroxypyridine N-oxide (6602-28-4) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 1.) Br2; 2.) NaOCH3 / 1.) 10percent aq. NaOH, 24 h; 2.) MeOH, DMF, RT, 1.5 h 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 7: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

2-bromo-pyridin-3-ol (6602-32-0) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 8 steps 1: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h 2: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 3: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 4: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 5: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 6: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 7: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 8: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

2-bromo-3-methoxypyridine (24100-18-3) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 7: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

2-bromo-3-methoxypyridine N-oxide (104819-48-9) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 6 steps 1: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 2: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 3: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 4: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 5: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 6: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

2-bromo,3-methoxy,4-nitropyridine-N-oxide (104819-50-3) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions

Yield

Multi-step reaction with 5 steps 1: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 2: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 3: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 4: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 5: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

pyridin-3-ylamine (462-08-8) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 9 steps 1: 82 percent / 15percent H2O2, conc. HCl 2: 38 percent 3: 54 percent / acetic anhydride, 30percent H2O2 4: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 5: Ambient temperature 6: PCl3 7: 25 percent / dimethylformamide / 4 h / 50 °C 8: 41 percent / Ac2O, H2O2 9: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

2-chloro-3-aminopyridine (6298-19-7) → 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0)

Conditions	Yield
Multi-step reaction with 8 steps 1: 38 percent 2: 54 percent / acetic anhydride, 30percent H2O2 3: 42 percent / 100percent HNO3/ 100percent H2SO4 containing 10percent SO3 4: Ambient temperature 5: PCl3 6: 25 percent / dimethylformamide / 4 h / 50 °C 7: 41 percent / Ac2O, H2O2 8: 30 percent / 33percent HBr, acetic acid / acetic acid / 4 h View Scheme

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0) → orelline (72016-31-0)

Conditions	Yield
at 220℃; under 0.01 Torr; sublimation;	50%
for 336h; Irradiation;

diazomethane (186581-53-3, 908094-01-9) + 3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0) → tetra-O-methylorellanine (101664-54-4) + 1,3,3',4'-Tetramethoxy<2,2'-bipyridin>-4(1H)-on-1'-oxid (109613-96-9) + 1,1',3,3'-Tetramethoxy<2,2'-bipyridin>-4,4'(1H,1'-H)-dion (109613-95-8)

Conditions	Yield
In methanol; diethyl ether	A 18% B 16% C 16%

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0) → C10H8N2O5

Conditions	Yield
at 180 - 200℃;

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide (37338-80-0) → orellanine anion radical

Conditions	Yield
With phosphate buffer; oxygen for 0.0166667h; Ambient temperature; tyrosinase;

Upstream product

• 101664-54-4 tetra-O-methylorellanine 
• 72016-31-0 orelline 
• 101664-55-5 3,3',4,4'-tetramethoxy-2,2'-bipyridine 
• 104819-52-5 2-bromo-3,4-dimethoxy pyridine 
• 105011-83-4 2-bromo-3,4-dimethoxy pyridine-N-oxide 
• 112516-35-5 3,4,3',4'-Tetramethoxy-[2,2']bipyridinyl 1-oxide 
• 33631-09-3 4-methoxypyridin-3-amine 
• 17282-04-1 2-chloro-3-fluoropyridine 
• 85386-94-3 2-Chlor-3-fluorpyridin-1-oxid 
• 101664-59-9 2-chloro-3,4-dimethoxypyridine 
• 101664-58-8 2-Chlor-3,4-dimethoxypyridin-1-oxid 
• 101664-56-6 2-Chlor-3-fluor-4-nitropyridin-1-oxid 
• 109613-98-1 2-bromo-3-fluoro-4-methoxypyridine 
• 109613-97-0 2-bromo-4-methoxy-pyridin-3-amine 

Downstream Products

• 72016-31-0 orelline 

Relevant articles and documents

Syntheses of Hydroxylated Bipyridines, I. - Orellanine, the Poison of a Toadstool

Two syntheses of orellanine, -3,3',4,4'-tetrol-1,1'-dioxide (5b), are developed which comprise 10 or 11 steps, respectively.The chemical reactions of 5b with diazomethane and on UV irradiation are described.

NEW REACTIONS OF PYRIDINES AND TOTAL SYNTHESIS OF THE FUNGAL TOXIN ORELLANINE

Dihalogenated pyridines react easily with sulphur nucleophiles, in dipolar aprotic solvents (DMF), to afford the products of mono- or of bis-substitution depending on the experimental conditions.On the contrary, with oxygen nucleophiles the bis-substituted products can be obtained only with some particular substrates.A new and efficient procedure to effect the homo-coupling of halogenoarenes will be presented.This reaction, wich occurs under the influence of low-valent nickel complexes, allowed us to effect the total synthesis of Orellanine, the lethal toxin of Cortinarius orellanus mushroom, as well as the syntheses of its decompositionproducts Orellinine and Orelline.The chemical properties of these three products and their behaviour towards UV irradiation will be presented and discussed.