4'-(3-Methyl-2-butyenyloxy)benzaldehyde

Base Information

• Chemical Name: 4'-(3-Methyl-2-butyenyloxy)benzaldehyde
• CAS No.: 28090-12-2
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Hs Code.: 2912299000
• DSSTox Substance ID: DTXSID20448389
• Nikkaji Number: J30.716E
• Wikidata: Q72488959
• Metabolomics Workbench ID: 126220
• ChEMBL ID: CHEMBL2022665
• Mol file: 28090-12-2.mol

Synonyms:Benzaldehyde, 4-[(3-methyl-2-butenyl)oxy]- (9CI);Benzaldehyde, p-[(3-methyl-2-butenyl)oxy]- (8CI);4-Prenyloxybenzaldehyde;4-[(3-Methyl-2-butenyl)oxy]benzaldehyde;

Chemical Property of 4'-(3-Methyl-2-butyenyloxy)benzaldehyde

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Boiling Point: 313.386 °C at 760 mmHg
• Flash Point: 137.749 °C
• PSA: 26.30000
• Density: 1.031 g/cm³
• LogP: 2.84410
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

4-(3-Methylbut-2-enoxy)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOC1=CC=C(C=C1)C=O)C
• Uses: 4-(3-Methylbut-2-enoxy)benzaldehyde is an analog of Curcumin(C838500) which is a natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and antioxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.Curcumin is currently being examined as a possible therapeutic for the treatment of Alzheimers disease. Neur

Technology Process of 4'-(3-Methyl-2-butyenyloxy)benzaldehyde

There total 9 articles about 4'-(3-Methyl-2-butyenyloxy)benzaldehyde 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%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + prenyl bromide (870-63-3) → 4-(3-methyl-but-2-enyloxy)-benzaldehyde (28090-12-2)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 9h;

DOI:10.1080/00397911003707204

Reference yield: 90.0%

2-[4-(3-methyl-but-2-enyloxy)-phenyl]-[1,3]dithiolane → 4-(3-methyl-but-2-enyloxy)-benzaldehyde (28090-12-2)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 4h; Heating;

DOI:10.1016/S0040-4039(02)00854-7

Reference yield: 85.0%

2-[4-(3-methyl-but-2-enyloxy)-phenyl]-[1,3]oxathiolane → 4-(3-methyl-but-2-enyloxy)-benzaldehyde (28090-12-2)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 3h; Heating;

DOI:10.1016/S0040-4039(02)00854-7

upstream raw materials:

4-hydroxy-benzaldehyde

prenyl bromide

3,3-dimethyl-allyl chloride

Downstream raw materials:

3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde

(1R,2S,5S)-2-[hydroxy-[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-4-methyl-dispiro[1,4-diazabicyclo[3.2.1]octan-3-one-7,1'-cyclohexane-4',2''-[1,3]dioxolane]

Refernces

• 1、 Gupta, Suraj K.,Mandal, Tanmoy,Gangber, Tejaswinee,Singh, Vivek,Choudhury, Joyanta. "Ancillary ligands switch the activity of Ru–NHC-based oxidation precatalysts". supporting information. . Retrieved 2019/10/28.
• 2、 Bisceglia, Federica,Seghetti, Francesca,Serra, Massimo,Zusso, Morena,Gervasoni, Silvia,Verga, Laura,Vistoli, Giulio,Lanni, Cristina,Catanzaro, Michele,De Lorenzi, Ersilia,Belluti, Federica. "Prenylated Curcumin Analogues as Multipotent Tools to Tackle Alzheimer's Disease". . p. 1420 - 1433. Retrieved 2019/01/11.