Ascochlorin

Base Information

• Chemical Name: Ascochlorin
• CAS No.: 26166-39-2
• Molecular Formula: C23H29 Cl O4
• Molecular Weight: 404.934
• UNII: PEZ8F05ODV
• ChEMBL ID: CHEMBL132623
• DSSTox Substance ID: DTXSID601102655
• Metabolomics Workbench ID: 98048
• Nikkaji Number: J16.919F
• Wikidata: Q24873644
• Mol file: 26166-39-2.mol

Synonyms:ascochlorin;ilicicolin D

Chemical Property of Ascochlorin

Chemical Property:

• Vapor Pressure: 5.2E-13mmHg at 25°C
• Melting Point: 172-174 °C
• Boiling Point: 556.9°Cat760mmHg
• PKA: 6.26±0.50(Predicted)
• Flash Point: 290.6°C
• PSA: 74.60000
• Density: 1.199g/cm³
• LogP: 5.55850
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 404.1754371
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

≥99.0% ^*data from raw suppliers

Ascochlorin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=O)C(C1(C)C=CC(=CCC2=C(C(=C(C(=C2O)Cl)C)C=O)O)C)C
• Isomeric SMILES: C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C(=C(C(=C2O)Cl)C)C=O)O)/C)C
• Uses: Ascochlorin is an antitumor fungal metabolite which specifically inhibits matrix metalloproteinase-9 (MMP-9) activity through suppression of activator protein-1 (AP-1)-dependent induction of MMP-9 gene expression. Via AP-1 suppression, ascochlorin selectively kills MX-1 cells, a human breast cancer cell line lacking estrogen receptors. Ascochlorin also shows activity against Newcastle disease and herpes simplex viruses. Ascochlorin is an isoprenoid antibiotic and antiviral that has diverse effects on mammalian cells. It suppresses PMA-induced invasion in renal carcinoma cells (IC50 = ~10 μM) by inhibiting the expression of matrix metalloproteinase-9. At 2 μM, ascochlorin profoundly increases the expression of p53 by increasing protein stability in cancer cells, and, at 50 μm, it inhibits signaling through STAT3. Ascochlorin also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking reduction of cytochrome b by ubiquinone.[Cayman Chemical]

Technology Process of Ascochlorin

There total 90 articles about Ascochlorin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.8%

3-chloro-4,6-dihydroxy-2-methyl-5-decane)-2,4-pentadienyl>benzaldehyde (91854-87-4,99529-53-0,109837-15-2) → (+/-) ascochlorin (26166-39-2,32433-87-7,85849-06-5,85849-07-6)

Guidance literature:

In tetrahydrofuran; water; acetic acid; at 60 ℃; for 5h;

DOI:10.1016/S0040-4020(01)90548-4

Reference yield: 81.0%

C31H45ClO8 (943911-93-1) → Ascochlorin (26166-39-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1246/cl.2007.654

Reference yield: 64.7%

Cylindrochlorin (23887-67-4) → Ascochlorin (26166-39-2)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; for 0.0833333h; under 760 Torr; Ambient temperature;

DOI:10.1248/cpb.42.953

upstream raw materials:

3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde

Cylindrochlorin

C₃₁H₄₅ClO₈

C₂₂H₂₅ClO₅S

Downstream raw materials:

3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate

2,4-Di-O-methylascochlorin

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