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CAS

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38462-04-3

(-)-Ascofuranone is a naturally occurring compound with antibiotic and antitumor properties. It is known for its ability to suppress gene activation related to matrix metalloproteinase-9 and has demonstrated effectiveness in treating Trypanosoma brucei brucei infection in mice.

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  • 38462-04-3 Structure

  • Basic information

    1. Product Name: ascofuranone
    2. Synonyms: ascofuranone;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
    3. CAS NO:38462-04-3
    4. Molecular Formula: C23H29ClO5
    5. Molecular Weight: 420.93
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 38462-04-3.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 581.2°C at 760 mmHg
    3. Flash Point: 305.3°C
    4. Appearance: /
    5. Density: 1.207g/cm3
    6. Vapor Pressure: 4.18E-14mmHg at 25°C
    7. Refractive Index: 1.577
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: ascofuranone(CAS DataBase Reference)
    11. NIST Chemistry Reference: ascofuranone(38462-04-3)
    12. EPA Substance Registry System: ascofuranone(38462-04-3)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 38462-04-3(Hazardous Substances Data)

38462-04-3 Usage

Uses

Used in Pharmaceutical Applications:
(-)-Ascofuranone is used as an antibiotic for its antitumor activity, targeting and suppressing PMA-mediated matrix metalloproteinase-9 gene activation through the Ras/Raf/MEK/ERKand Ap1-dependent mechanisms. This makes it a potential candidate for the development of new cancer treatments.
Used in Infectious Disease Treatment:
In the field of infectious diseases, (-)-Ascofuranone is used as a therapeutic agent for treating Trypanosoma brucei brucei infection in mice, showcasing its potential in combating parasitic infections.

Safety Profile

Moderately toxic byintraperitoneal route. Whenheated to decomposition it emits toxic fumes of Cl-.

Check Digit Verification of cas no

The CAS Registry Mumber 38462-04-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,4,6 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 38462-04:
(7*3)+(6*8)+(5*4)+(4*6)+(3*2)+(2*0)+(1*4)=123
123 % 10 = 3
So 38462-04-3 is a valid CAS Registry Number.
InChI:InChI=1/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

38462-04-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product 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

1.2 Other means of identification

Product number -
Other names Ascofuranon

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:38462-04-3 SDS

38462-04-3Synthetic 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

38462-04-3Upstream product

38462-04-3Relevant articles and documents

SYNTHESIS OF THE NATURAL ENANTIOMERS OF ASCOCHLORIN, ASCOFURANONE AND ASCOFURANOL

Mori, Kenji,Takechi, Shozo

, p. 3049 - 3062 (2007/10/02)

Three fungal metabolites with a common structural feature as prenylated phenols were synthesized in their naturally occuring and optically active forms: ascochlorin benzaldehyde>, ascofuranone and ascofuranol benzaldehyde>. (+)-Ascofuranone and (+)-ascofuranol were also synthesized.By the present synthesis the absolute configuration of the natural (-)-ascofuranol was established as (1''S,4''S).

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