Product Name

  • Name

    ascofuranone

  • EINECS
  • CAS No. 38462-04-3
  • Article Data1
  • CAS DataBase
  • Density 1.207g/cm3
  • Solubility
  • Melting Point
  • Formula C23H29ClO5
  • Boiling Point 581.2°C at 760 mmHg
  • Molecular Weight 420.933
  • Flash Point 305.3°C
  • Transport Information
  • Appearance
  • Safety Moderately toxic by intraperitoneal route. See also ALDEHYDES. When heated to decomposition it emits toxic fumes of Cl−.
  • Risk Codes
  • Molecular Structure Molecular Structure of 38462-04-3 (ascofuranone)
  • Hazard Symbols
  • Synonyms C23H29ClO5;Ascofuranone;Ascofuranon;
  • PSA 83.83000
  • LogP 5.22400

Synthetic route

(1''S,4''S)-(-)-ascofuranol
51759-79-6

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

Ascofuranone
38462-04-3

Ascofuranone

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 3h; Ambient temperature;22.2%
(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate
99529-56-3

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

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

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

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

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

Ascofuranone
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
(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
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

Ascofuranone
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
(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
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

Ascofuranone
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
(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
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

Ascofuranone
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
(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
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

Ascofuranone
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
Acetic acid (2E,6E)-7-[(2S,4S)-5,5-dimethyl-4-((R)-1-naphthalen-1-yl-ethylcarbamoyloxy)-tetrahydro-furan-2-yl]-3-methyl-octa-2,6-dienyl ester
99477-56-2

Acetic acid (2E,6E)-7-[(2S,4S)-5,5-dimethyl-4-((R)-1-naphthalen-1-yl-ethylcarbamoyloxy)-tetrahydro-furan-2-yl]-3-methyl-octa-2,6-dienyl ester

Ascofuranone
38462-04-3

Ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 76.3 percent / Et3N, HSiCl3 / benzene / 96 h / Ambient temperature
2: imidazole / dimethylformamide / 6 h / Ambient temperature
3: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature
4: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C
5: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C
6: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature
7: 57 percent / DBU / tetrahydrofuran / 6 h / Heating
8: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.
9: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature
10: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
acetic anhydride
108-24-7

acetic anhydride

Ascofuranone
38462-04-3

Ascofuranone

2,4-O-di-acetylascofuranone

2,4-O-di-acetylascofuranone

Conditions
ConditionsYield
With pyridine at 20℃; Product distribution / selectivity;100%
Ascofuranone
38462-04-3

Ascofuranone

dimethyl sulfate
77-78-1

dimethyl sulfate

4-O-Methyl-ascofuranone

4-O-Methyl-ascofuranone

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Heating / reflux;93%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

Ascofuranone
38462-04-3

Ascofuranone

ethyl {2-chloro-6-[(2E,6E)-7-((S)-2,2-dimethyl-3-oxotetrahydrofuran-5-yl)-3-methyl-2,6-octadienyl]-4-formyl-5-hydroxy-3-methylphenoxy}acetate

ethyl {2-chloro-6-[(2E,6E)-7-((S)-2,2-dimethyl-3-oxotetrahydrofuran-5-yl)-3-methyl-2,6-octadienyl]-4-formyl-5-hydroxy-3-methylphenoxy}acetate

Conditions
ConditionsYield
Stage #1: Ascofuranone With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 40℃; for 5.5h;		88%
Ascofuranone
38462-04-3

Ascofuranone

methyl iodide
74-88-4

methyl iodide

4-O-Methyl-ascofuranone

4-O-Methyl-ascofuranone

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Heating;87%
acetic anhydride
108-24-7

acetic anhydride

Ascofuranone
38462-04-3

Ascofuranone

4-O-Acetyl-ascofuranone
60217-09-6

4-O-Acetyl-ascofuranone

Conditions
ConditionsYield
With pyridine at 20℃;68%
pyridine-3-carbonyl chloride hydrochloride
20260-53-1

pyridine-3-carbonyl chloride hydrochloride

Ascofuranone
38462-04-3

Ascofuranone

4-O-Nicotinoyl-ascofuranone

4-O-Nicotinoyl-ascofuranone

Conditions
ConditionsYield
With pyridine at 20℃;67%
isonicotinoyl chloride hydrochloride
39178-35-3

isonicotinoyl chloride hydrochloride

Ascofuranone
38462-04-3

Ascofuranone

4-O-Isonicotinoyl-ascofuranone

4-O-Isonicotinoyl-ascofuranone

Conditions
ConditionsYield
In pyridine at 20℃; for 1h;54%
Stage #1: isonicotinoyl chloride hydrochloride; Ascofuranone With pyridine at 20℃; for 1h;
Stage #2: With water at 20℃; for 0.5h;		54%
glutaric anhydride,
108-55-4

glutaric anhydride,

Ascofuranone
38462-04-3

Ascofuranone

4-O-(4-Carboxybutanoyl)ascofuranone

4-O-(4-Carboxybutanoyl)ascofuranone

Conditions
ConditionsYield
With pyridine; dmap at 50℃;32%
Ascofuranone
38462-04-3

Ascofuranone

3-chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)octyl]-benzaldehyde
1027952-60-8

3-chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)octyl]-benzaldehyde

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In ethanol at 0℃; for 3h;25%
Ascofuranone
38462-04-3

Ascofuranone

Dehydroascofuranone

Dehydroascofuranone

Conditions
ConditionsYield
With sodium hydroxide; silver nitrate In 1,4-dioxane at 20℃; for 3h;24%
With sodium hydroxide; silver nitrate In 1,4-dioxane; water at 20℃; for 3h;24%
Ascofuranone
38462-04-3

Ascofuranone

5-[(E,E)-7-(3-chloro-2,6-dihydroxy-5-hydroxyiminomethyl-4-methylphenyl)-1,5-dimethyl-1,5-heptadienyl]-4,5-dihydro-2,2-dimethyl-3(2H)-furanone

5-[(E,E)-7-(3-chloro-2,6-dihydroxy-5-hydroxyiminomethyl-4-methylphenyl)-1,5-dimethyl-1,5-heptadienyl]-4,5-dihydro-2,2-dimethyl-3(2H)-furanone

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride at 20 - 25℃; for 3.5h;20%
Ascofuranone
38462-04-3

Ascofuranone

2-O-Methyl-ascofuranone

2-O-Methyl-ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / pyridine / 20 °C
2: 24 percent / K2CO3 / acetone / 2 h / Heating
3: 90 percent / aq. NaOH / methanol / 4 h / 20 °C
View Scheme
Ascofuranone
38462-04-3

Ascofuranone

4-O-Acetyl-2-O-methyl-ascofuranone
290361-56-7

4-O-Acetyl-2-O-methyl-ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / pyridine / 20 °C
2: 24 percent / K2CO3 / acetone / 2 h / Heating
View Scheme
Ascofuranone
38462-04-3

Ascofuranone

4-O-Carboxymethyl-ascofuranone

4-O-Carboxymethyl-ascofuranone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaH / dimethylformamide / 0.17 h / 20 °C
1.2: 88 percent / dimethylformamide / 5.5 h / 40 °C
2.1: 91 percent / aq. K2CO3 / methanol / 2 h / 20 °C
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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