26166-39-2

Basic information

• Product Name: ascochlorin
• Synonyms: ascochlorin;3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R)-1β,2β,6β-trimethyl-3-oxocyclohexyl]-2,4-pentadienyl]benzaldehyde;Ilicicolin D;3-Chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)benzaldehyde (1R-(1alpha(2E,4E),2beta,6beta))-;Antibiotic ll-Z1272 gamma;Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (1R-(1alpha(2E,4E),2beta,6beta))-;beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (E,E)-;Ll-Z 1272 gamma
• CAS NO: 26166-39-2
• Molecular Formula: C₂₃H₂₉ClO₄
• Molecular Weight: 404.931
• Mol File: 26166-39-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 172-174 °C
• Boiling Point: 556.9°Cat760mmHg
• Flash Point: 290.6°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 5.2E-13mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble
• PKA: 6.26±0.50(Predicted)
• CAS DataBase Reference: ascochlorin(CAS DataBase Reference)
• NIST Chemistry Reference: ascochlorin(26166-39-2)
• EPA Substance Registry System: ascochlorin(26166-39-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 26166-39-2(Hazardous Substances Data)

Usage

Description

Ascochlarin is an antitumor fungal metabolite that exhibits a range of biological activities, including the inhibition of matrix metalloproteinase-9 (MMP-9) activity and suppression of activator protein-1 (AP-1)-dependent induction of MMP-9 gene expression. It is an isoprenoid antibiotic and antiviral that has diverse effects on mammalian cells.

Uses

Used in Anticancer Applications:
Ascochlarin is used as an antitumor agent for selectively targeting and killing MX-1 cells, a human breast cancer cell line lacking estrogen receptors. It achieves this through the suppression of AP-1, which in turn inhibits the induction of MMP-9 gene expression. Ascochlarin also demonstrates activity against various types of cancer by increasing the expression of p53 and inhibiting signaling through STAT3.
Used in Antiviral Applications:
Ascochlarin is used as an antiviral agent for its activity against Newcastle disease and herpes simplex viruses, providing potential therapeutic benefits in the treatment of these viral infections.
Used in Drug Delivery Systems:
Ascochlarin is used as a compound to suppress PMA-induced invasion in renal carcinoma cells by inhibiting the expression of matrix metalloproteinase-9. It also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking the reduction of cytochrome b by ubiquinone, which may have implications for the development of novel drug delivery systems to enhance its therapeutic outcomes.

InChI:InChI=1/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10-,13-6+

Upstream product

• 54812-37-2 2-iodo-1,3-dimethoxy-5-methylbenzene 
• 2816-57-1 2,6-dimethylcyclohexanone 
• 943911-96-4 C₂₁H₂₅ClO₄S 
• 943911-90-8 C₂₁H₂₆O₄S 
• 943911-89-5 C₁₂H₂₀O₃ 
• 943911-98-6 C₁₃H₂₂O₂ 
• 943911-94-2 C₁₁H₁₈O 
• 943911-88-4 C₂₆H₃₃ClO₈S 
• 943911-92-0 C₂₄H₂₉ClO₇S 
• 943911-97-5 C₂₀H₂₁ClO₅S 
• 943911-91-9 C₂₂H₂₅ClO₅S 
• 23887-67-4 Cylindrochlorin 
• 85785-69-9 (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde 
• 85785-68-8 (4R,5R)-4,5-Dimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde 

Downstream Products

• 38561-39-6 2-O-Methylascochlorin 
• 38561-38-5 2-chloro-4-formyl-5-methoxy-3-methyl-6-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate 
• 290361-55-6 4-O-(Ethoxycarbonyl)methyl-2-O-methylascochlorin 
• 611217-63-1 3-acetoxy-4-chloro-6-(1,3-dioxolan-2-yl)-5-methyl-2-[(E)-2,3-epoxy-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl)-2,4-pentadienyl]phenyl acetate 
• 611217-61-9 3-acetoxy-4-chloro-6-(1,3-dioxolan-2-yl)-5-methyl-2-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxaspiro[4.5]dec-7-yl)-2,4-pentadienyl]phenyl acetate 
• 26166-39-2 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2Z,4E)-3-methyl-5-((1S,2S,6S)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde 

Relevant articles and documents

A novel testosterone 5α-reductase inhibitor, 8',9'-dehydroascochlorin produced by Verticillium sp. FO-2787

A new testosterone 5α-reductase inhibitor, 8',9'-dehydroascochlorin, was isolated from the cultured mycelium of Verticillium sp. FO-2787. This compound (M.W.: 402, C23H27ClO4) consists of 5-chloroorcylic aldehyde and 2,3,4

Total synthesis of (-)-ascochlorin via a cyclobutenone-based benzannulation strategy.

The application of a convergent benzannulation strategy in an efficient synthesis of (-)-ascochlorin is described.

SYNTHESIS OF THE NATURAL ENANTIOMERS OF ASCOCHLORIN, ASCOFURANONE AND ASCOFURANOL

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).