CAS 38462-04-3

Ascofuranone

Description:

Ascofuranone, with the CAS number 38462-04-3, is a naturally occurring compound classified as a furanone. It is primarily derived from certain fungi, particularly those belonging to the genus Ascochyta. This compound is characterized by its unique bicyclic structure, which includes a furan ring fused to a carbonyl group, contributing to its distinctive chemical properties. Ascofuranone exhibits biological activity, including antimicrobial and antifungal properties, making it of interest in pharmaceutical and agricultural research. Its solubility in organic solvents and relatively low solubility in water are notable characteristics, influencing its applications in various fields. Additionally, Ascofuranone's stability under certain conditions allows for its use in formulations where prolonged efficacy is desired. The compound's potential as a lead structure for the development of new therapeutic agents highlights its significance in medicinal chemistry. Overall, Ascofuranone represents a fascinating example of how natural products can inspire innovative solutions in science and industry.

Formula: C₂₃H₂₉ClO₅

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

InChI key: InChIKey=VGYPZLGWVQQOST-JUERRSSISA-N

SMILES: C(/C=C(/CC/C=C(\C)/[C@@H]1CC(=O)C(C)(C)O1)\C)C2=C(O)C(C=O)=C(C)C(Cl)=C2O

Synonyms:

• 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]benzaldehyde
• Ascofuranone
• Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadienyl]-
• Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl]-, [S-(E,E)]-
• benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]-

Ascofuranone

CAS: 38462-04-3

Ascofuranone is a natural compound that can be extracted from the bark of the asafoetida plant. It has been shown to inhibit the activity of enzymes, such as benzaldehyde oxidase and catechol oxidase, with an oxidation catalyst. The binding of this inhibitor to its target enzyme alters the reaction mechanism by changing the intramolecular hydrogen bonding in the active site and reducing the affinity for substrate. This inhibition causes a decrease in activity of these enzymes, which prevents them from synthesizing molecules that are important for energy metabolism. Ascofuranone has also been shown to have anti-cancer properties against breast cancer cells in vitro and in vivo.

Formula: C₂₃H₂₉CIO₅

Purity: Min. 95%

Molecular weight: 524.39 g/mol

Ref: 3D-FA163237

(-)-Ascofuranone

Controlled Product

CAS: 38462-04-3

Formula: C₂₃H₂₉ClO₅

Color and Shape: Neat

Molecular weight: 420.926

Ref: TR-A787035

Ascofuranone

CAS: 38462-04-3

Ascofuranone is an inhibitor of the ubiquinol oxidase activity of Trypanosoma brucei mitochondrial alternative oxidase (TAO), as well as an inhibitor of HsDHODH

Formula: C₂₃H₂₉ClO₅

Color and Shape: Solid

Molecular weight: 420.93

Ref: TM-T69313