Climacostol

Base Information

• Chemical Name: Climacostol
• CAS No.: 253158-28-0
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• DSSTox Substance ID: DTXSID90443780
• Nikkaji Number: J1.195.264J
• Wikidata: Q76415918
• Metabolomics Workbench ID: 75856
• Mol file: 253158-28-0.mol

Synonyms:climacostol

Chemical Property of Climacostol

Chemical Property:

• Boiling Point: 374.2±17.0 °C(Predicted)
• PKA: 9.44±0.10(Predicted)
• PSA: 40.46000
• Density: 1.026±0.06 g/cm3(Predicted)
• LogP: 4.16690
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 203

Purity/Quality:

98%Min ^*data from raw suppliers

Climacostol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CCC1=CC(=CC(=C1)O)O
• Isomeric SMILES: CCCCCC/C=C\CC1=CC(=CC(=C1)O)O
• General Description: Climacostol is a resorcinolic lipid toxin produced by the protozoan *Climacostomum virens* as a defense mechanism against predators. Recent studies on its synthetic analogues, such as AN1 and AN2, have demonstrated enhanced bioactivity, including increased toxicity against microbes and protists, as well as the ability to induce programmed cell death. These findings highlight the potential for structural modifications to optimize the potency and mechanism of action of climacostol-derived compounds.

Technology Process of Climacostol

There total 12 articles about Climacostol 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: 98.0%

(Z)-1-[(3,5-dimethoxymethoxy)phenyl]non-2'-ene (1235555-59-5) → 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene (253158-28-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; at 20 ℃;

DOI:10.1055/S-0029-1218695

Reference yield: 91.0%

1,3-bis(tert-butyldimethylsilyloxy)-5-[(Z)-2'-nonenyl]benzene (252913-16-9) → 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene (253158-28-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1271/bbb.65.2110

Reference yield:

3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde (187803-40-3) → 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene (253158-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C

2.1: Co₂(CO)6 / diethyl ether / -20 - 25 °C

2.2: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 0.5 h / Heating

2.3: 73 mg / n-Bu₃SnH / benzene / 3 h / 65 °C

3.1: 86 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C

With n-butyllithium; hexacarbonyldicobalt; pyridine hydrogenfluoride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1016/j.tet.2003.09.105

upstream raw materials:

1,3-bis(tert-butyldimethylsilyloxy)-5-[(Z)-2'-nonenyl]benzene

n-octyne

3,5-dihydroxybenzaldehyde

3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde

Refernces

Bioactivity and structural properties of novel synthetic analogues of the protozoan toxin climacostol

10.3390/toxins11010042

The research investigates the bioactivity and structural properties of novel synthetic analogues of the protozoan toxin climacostol, a resorcinolic lipid produced by the protozoan Climacostomum virens for defense against predators. The study synthesized two new analogues, AN1 (2-methyl-5[(2Z)-non-2-en-1-yl]benzene-1,3-diol) and AN2 (5-[(2Z)-non-2-en-1-yl]benzene-1,2,3-triol), with the aim of increasing the activity of the native toxin. The research evaluated the effects of these analogues on prokaryotic and free-living protists, as well as on mammalian tumor cells. The results showed that AN1 exhibited higher toxicity against pathogen microbes and protists than climacostol, while AN2 demonstrated the ability to induce programmed cell death in protistan cells. The study provides insights into the structure–activity relationships of climacostol and its analogues, suggesting that modifications to the aromatic ring can effectively modulate their potency and mechanism of action. The chemicals involved in this research include the native climacostol, its synthetic analogues AN1 and AN2, and various reagents used in the synthesis and analysis processes, such as n-BuLi, MeI, TBAF, DMP, and others.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 253158-28-0 Climacostol

Send

Send

Metric Ton KG G Pound L ML

Send

Send