Goniothalamin

Base Information

• Chemical Name: Goniothalamin
• CAS No.: 17303-67-2
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.237
• NSC Number: 104956
• UNII: 34W9GO6B2Z
• DSSTox Substance ID: DTXSID801035678
• Nikkaji Number: J179.716F
• Wikidata: Q27256393
• Metabolomics Workbench ID: 136556
• ChEMBL ID: CHEMBL464443
• Mol file: 17303-67-2.mol

Synonyms:goniothalamin

Chemical Property of Goniothalamin

Chemical Property:

• Vapor Pressure: 3.67E-06mmHg at 25°C
• Boiling Point: 386°Cat760mmHg
• Flash Point: 162.2°C
• PSA: 26.30000
• Density: 1.21g/cm³
• LogP: 2.57150
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

Goniothalamin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(=O)OC1C=CC2=CC=CC=C2
• Isomeric SMILES: C1C=CC(=O)O[C@H]1/C=C/C2=CC=CC=C2
• General Description: Goniothalamin is a natural styryl lactone with demonstrated cytotoxic and antiproliferative effects against various cancer cell lines. Its structural analogues, such as 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, have been explored to enhance its anticancer activity, with modifications like trifluoromethyl groups showing comparable cytotoxicity, indicating potential for improved electrophilic reactivity and therapeutic efficacy.

Technology Process of Goniothalamin

There total 170 articles about Goniothalamin 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: 100.0%

(R)-6-(2-Benzenesulfinyl-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (143724-96-3) → (R)-goniothalamin (22639-28-7,57885-00-4,118204-01-6,122046-62-2,17303-67-2)

Guidance literature:

With calcium carbonate; In toluene; for 1h; Heating;

DOI:10.1016/S0957-4166(00)82182-5

Reference yield: 98.0%

(1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate (639798-55-3) → (R)-goniothalamin (22639-28-7,57885-00-4,118204-01-6,122046-62-2,17303-67-2)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; for 12h; Heating;

DOI:10.1016/j.tetlet.2003.09.122

Reference yield: 91.0%

(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one (70670-14-3) → (R)-goniothalamin (22639-28-7,57885-00-4,118204-01-6,122046-62-2,17303-67-2)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at -35 ℃; for 4h;

DOI:10.1248/cpb.42.839

upstream raw materials:

tert.-butylhydroperoxide

(E)-2-styryl-3,4-dihydro-2H-pyran

(E)-7-phenyl-6-ene-5-hydroxy-2-heptinoic acid

6-tert-Butylperoxy-2-((E)-styryl)-3,6-dihydro-2H-pyran

Downstream raw materials:

(R)-goniothalamin

(S)-goniothalamin

(6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one

(1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one

Refernces

Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

10.1016/j.bmc.2013.06.044

The study presents the design, synthesis, and in vitro evaluation of a new series of goniothalamin analogues, specifically 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, which are based on the structure of goniothalamin, a natural styryl lactone with known cytotoxic and antiproliferative activities against various cancer cell lines. The researchers prepared a focused library of 17 analogues and assessed their cytotoxicity against eight human cancer cell lines. The purpose of these chemical compounds was to potentially enhance the cytotoxic profile of goniothalamin and to contribute to a better understanding of the structure-activity relationship, which could aid in the design of more active and selective anticancer agents. The analogues with trifluoromethyl groups on the aromatic ring showed similar cytotoxicity to goniothalamin, suggesting that these modifications could activate the inhibitor's electrophilic site, thereby increasing cytotoxicity.

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