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Orellanine
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Name

Orellanine

 EINECS N/A
CAS No. 37338-80-0 Density 1.777 g/cm3
PSA 124.92000 LogP -0.43720
Solubility N/A Melting Point N/A
Formula C10H8N2O6 Boiling Point 834.615 °C at 760 mmHg
Molecular Weight 252.183 Flash Point 458.558 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 37338-80-0 (orellanine) Hazard Symbols N/A
Synonyms

3,3',4,4'-Tetrahydroxy-2,2'-bipyridine-1,1'-dioxide;

Article Data 4

Orellanine Synthetic route

72016-31-0

orelline

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
With dihydrogen peroxide for 8h; Ambient temperature;87%
for 336h; Irradiation; isomerisation also without irradiation;
101664-54-4

tetra-O-methylorellanine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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%
101664-55-5

3,3',4,4'-tetramethoxy-2,2'-bipyridine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
104819-52-5

2-bromo-3,4-dimethoxy pyridine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
105011-83-4

2-bromo-3,4-dimethoxy pyridine-N-oxide

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
112516-35-5

3,4,3',4'-Tetramethoxy-[2,2']bipyridinyl 1-oxide

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: m-chloroperbenzoic acid
2: 60 percent / 48percent HBr / 120 °C
View Scheme
33631-09-3

4-methoxypyridin-3-amine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
17282-04-1

2-chloro-3-fluoropyridine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
85386-94-3

2-Chlor-3-fluorpyridin-1-oxid

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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
101664-59-9

2-chloro-3,4-dimethoxypyridine

37338-80-0

3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide

Conditions
ConditionsYield
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

Orellanine Specification

The CAS registry number of [2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide is 37338-80-0. It is a pyridine N-oxide and a crystalline alkaloid that is found naturally in some lifeforms. In addition, the molecular formula is C10H8N2O6 and the molecular weight is 252.17. What's more, it has been found in at least five species of mushrooms in the Cortinariaceae family.

Physical properties about [2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide are: (1)ACD/LogP: -3.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4; (4)ACD/LogD (pH 7.4): -7; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 131.84 Å2; (13)Index of Refraction: 1.728; (14)Molar Refractivity: 56.554 cm3; (15)Molar Volume: 141.911 cm3; (16)Polarizability: 22.42 ×10-24cm3; (17)Surface Tension: 86.76 dyne/cm; (18)Density: 1.777 g/cm3; (19)Flash Point: 458.558 °C; (20)Enthalpy of Vaporization: 125.458 kJ/mol; (21)Boiling Point: 834.615 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][n+]1ccc(O)c(O)c1c2[n+]([O-])ccc(O)c2O
(2)Std. InChI: InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,13-16H
(3)Std. InChIKey: JEWWXPOUSBVQKG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 4900ug/kg (4.9mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.
guinea pig LD50 intraperitoneal 8mg/kg (8mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.
mouse LD50 intraperitoneal 12480ug/kg (12.48mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.
mouse LD50 oral 33mg/kg (33mg/kg)   Archives of Toxicology. Vol. 62, Pg. 81, 1988.
mouse LD50 subcutaneous 8300ug/kg (8.3mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 12, Pg. 491, 1961.

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