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Ascofuranone
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Name

Ascofuranone

 EINECS N/A
CAS No. 38462-04-3 Density 1.207g/cm3
PSA 83.83000 LogP 5.22400
Solubility N/A Melting Point N/A
Formula C23H29ClO5 Boiling Point 581.2°C at 760 mmHg
Molecular Weight 420.933 Flash Point 305.3°C
Transport Information N/A Appearance N/A
Safety Moderately toxic by intraperitoneal route. See also ALDEHYDES. When heated to decomposition it emits toxic fumes of Cl−. Risk Codes N/A
Molecular Structure Molecular Structure of 38462-04-3 (ascofuranone) Hazard Symbols N/A
Synonyms

C23H29ClO5;Ascofuranone;Ascofuranon;

Article Data 1

Ascofuranone Synthetic route

51759-79-6

(1''S,4''S)-(-)-ascofuranol

38462-04-3

Ascofuranone

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 3h; Ambient temperature;22.2%
99529-56-3

(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: imidazole / dimethylformamide / 6 h / Ambient temperature
2: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature
3: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C
4: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
5: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
6: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
7: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
8: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
9: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-55-1, 99529-54-1, 99529-56-3, 99529-57-4

(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 5.14 g / 14 h / 80 °C
2: 76.3 percent / Et3N, HSiCl3 / benzene / 96 h / Ambient temperature
3: imidazole / dimethylformamide / 6 h / Ambient temperature
4: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature
5: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C
6: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
7: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
8: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
9: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
10: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
11: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-58-4

(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadien-1-ol

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C
2: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
3: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
4: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
5: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
6: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
7: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-59-5

(2E,6E,1'S,4'S)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl chloride

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
2: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
3: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
4: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
5: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
6: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-57-3, 99529-58-5

(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature
2: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C
3: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
4: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
5: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
6: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
7: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
8: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-60-8

(2'E,6'E,1''S,4''S)-(+)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
2: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
3: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
4: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
5: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-62-0

(2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
2: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
3: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-61-9

(2'E,6'E,1''S,4''S)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
2: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
3: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
4: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
99477-63-1

(2'E,6'E,1''S,4''S)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde

38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
2: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme

Ascofuranone Chemical Properties


IUPAC Name: 5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde 
Molecular Weight: 420.92636 g/mol
Molecular Formula: C23H29ClO5 
Density: 1.207 g/cm3 
Boiling Point: 581.2 °C at 760 mmHg
Flash Point: 305.3 °C
Vapour Pressure: 4.18E-14 mmHg at 25°C
Index of Refraction: 1.577 Molar
Refractivity: 115.63 cm3
Molar Volume: 348.6 cm3
Polarizability: 45.84*10-24cm3
Surface Tension: 47.5 dyne/cm 
Enthalpy of Vaporization: 90.13 kJ/mol 
XLogP3-AA: 5.5
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 7
Tautomer Count: 50
Exact Mass: 420.170352
MonoIsotopic Mass: 420.170352
Topological Polar Surface Area: 83.8
Heavy Atom Count: 29
Complexity: 668 
Defined Atom StereoCenter Count: 1
Isomeric SMILES: CC1=C(C(=C(C(=C1Cl)O)C/C=C(\C)/CC/C=C(\C)/[C@@H]2CC(=O)C(O2)(C)C)O)C=O
InChI: InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
InChIKey: VGYPZLGWVQQOST-JUERRSSISA-N

Ascofuranone Uses

 Ascofuranone (CAS NO.38462-04-3) is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness. And it is an antibiotic produced by the fungus Ascochyta visiae that inhibits the Trypanosoma brucei alternative oxidase. The compound is effective both in infections in mice and in vitro cell culture. Ascofuranone has also been reported to have anti-tumor activity, and modulate the immune system.

Ascofuranone Toxicity Data With Reference

1.    

ipr-rat LD50:1350 mg/kg

     JANTAJ    Journal of Antibiotics. 26 (1973),681.
2.    

ipr-mus LD50:2220 mg/kg

     JANTAJ    Journal of Antibiotics. 26 (1973),681.

Ascofuranone Safety Profile

Moderately toxic by intraperitoneal route. See also ALDEHYDES. When heated to decomposition it emits toxic fumes of Cl−.

Ascofuranone Specification

The Ascofuranone (CAS NO.38462-04-3) is also called 2-Methyl-3-chloro-4,6-dihydroxy-5-[(2E,6E)-3-methyl-7-[(2S)-4-oxo-5,5-dimethyltetrahydrofuran-2-yl]-2,6-octadienyl]benzaldehyde ; 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(S)-tetrahydro-5,5-dimethyl-4-oxofuran-2-yl]-2,6-octadienyl]benzaldehyde ; Ascofranone ; Ascofuranon . Ascofuranone (CAS NO.38462-04-3) is high toxic. It can produce toxic chloride smoke when buring. So the storage environment should be ventilate, low-temperature and dry.

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