Butylidenephthalide

Base Information

• Chemical Name: Butylidenephthalide
• CAS No.: 551-08-6
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• European Community (EC) Number: 208-991-3
• UNII: 2JL3MHX6ZE
• DSSTox Substance ID: DTXSID9060281
• Wikidata: Q27890207
• Metabolomics Workbench ID: 45243
• ChEMBL ID: CHEMBL1765390
• Mol file: 551-08-6.mol

Synonyms:3-butylidene-1(3H)-isobenzofuranone;3-butylidenephthalide;butylidenephthalide;n-butylidenephthalide

Chemical Property of Butylidenephthalide

Chemical Property:

• Vapor Pressure: 0.000545mmHg at 25°C
• Melting Point: 82.5°C
• Refractive Index: n20/D 1.577(lit.)
• Boiling Point: 312°Cat760mmHg
• Flash Point: 113 ºC
• PSA: 26.30000
• Density: 1.204 g/cm³
• LogP: 2.99800
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.083729621
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

3-Butylidenephthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=C1C2=CC=CC=C2C(=O)O1
• Isomeric SMILES: CCC/C=C/1\C2=CC=CC=C2C(=O)O1
• Description: N-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder. It is a bioactive phthalide compound of Chuanxiong rhizoma, a Chinese herbal medicine used for treating headache obtained from the root of Ligusticum chuanxiong Hort. It has found that it can regulate tumor stem cell genes EZH2/AXL and reduced its migration and invasion in glioblastoma. Moreover, it can induce apoptosis in the A549 human lung adenocarcinoma cell line by coupled down-regulation of AP-2a and telomerase activity. Therefore, it is a potential cancer chemotherapy drug. Moreover, It can also exhibit protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3. Finally, it has certain antiplatelet effect.
• Uses: 3-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder.

Technology Process of Butylidenephthalide

There total 10 articles about Butylidenephthalide 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: 87.0%

carbon monoxide (201230-82-2) + 1-(2-bromo-phenyl)-pentan-1-one (79784-61-5) → 3-butylidenephthalide (551-08-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 100 ℃; for 3h;

DOI:10.1016/0022-328X(90)80087-G

Reference yield: 76.1%

phthalic anhydride (85-44-9) + pentanoic anhydride (2082-59-9) → 3-butylidenephthalide (551-08-6)

Guidance literature:

With sodium valerate; at 170 - 190 ℃; for 4h;

Reference yield: 59.0%

1-(2-bromo-phenyl)-pentan-1-one (79784-61-5) → 3-Butylideneisoindolinone (20871-40-3) + 3-butylidenephthalide (551-08-6)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; at 100 ℃; for 16h;

DOI:10.1021/ja00192a034

upstream raw materials:

phthalic anhydride

pentanoic anhydride

di-n-butylcadmium

formic acid

Downstream raw materials:

butylphthalide

2-(1-oxypentyl)-benzoic acid methyl ester

1-(2-(hydroxymethyl)phenyl)pentan-1-ol