550-37-8

Basic information

• Product Name: 2-PENTANOYLBENZOIC ACID
• Synonyms: LIGUSTICUMIC ACID;2-VALERYLBENZOIC ACID;2-PENTANOYLBENZOIC ACID;O-VALERYLBENZOIC ACID;2-Valerylbenzoic acid Ligusticumic acid o-Valerylbenzoic acid;2-(1-Oxopentyl)benzoic acid;Butylphthalide Impurity 3
• CAS NO: 550-37-8
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• Mol File: 550-37-8.mol

Chemical Properties

• Boiling Point: 353.8 °C at 760 mmHg
• Flash Point: 182 °C
• Appearance: /
• Density: 1.126g/cm³
• Vapor Pressure: 1.29E-05mmHg at 25°C
• Refractive Index: 1.536
• PKA: 3.40±0.36(Predicted)
• CAS DataBase Reference: 2-PENTANOYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PENTANOYLBENZOIC ACID(550-37-8)
• EPA Substance Registry System: 2-PENTANOYLBENZOIC ACID(550-37-8)

Safety Data

• Hazardous Substances Data: 550-37-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PENTANOYLBENZOIC ACID is used as an intermediate in the synthesis of various pharmaceutical compounds, such as N-butylphthalide, which is known to alleviate blood-brain barrier impairment in rats exposed to carbon monoxide. Its unique structure allows it to be a versatile building block for the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
2-PENTANOYLBENZOIC ACID is used as a key component in the synthesis of various organic compounds, including those with potential applications in the fields of materials science, agrochemicals, and specialty chemicals. Its reactivity and functional groups make it a valuable precursor for the creation of novel molecules with specific properties and functions.
Used in Research and Development:
2-PENTANOYLBENZOIC ACID serves as a valuable research tool for scientists and researchers working on the development of new chemical processes, materials, and pharmaceuticals. Its unique structure and properties can provide insights into the behavior of similar compounds and contribute to the advancement of scientific knowledge in various fields.

InChI:InChI=1/C12H14O3/c1-2-3-8-11(13)9-6-4-5-7-10(9)12(14)15/h4-7H,2-3,8H2,1H3,(H,14,15)

Upstream product

• 64624-87-9 2-(1-oxypentyl)-benzoic acid methyl ester 
• 109-65-9 1-bromo-butane 
• 85-44-9 phthalic anhydride 
• 693-03-8 n-butyl magnesium bromide 
• 3431-67-2 di-n-butylcadmium 
• 72917-31-8 (Z)-3-(1-butylidene)phthalide 
• 2306-33-4 monoethyl phthalate 
• 4376-18-5 Monomethyl phthalate 

Downstream Products

• 64624-87-9 2-(1-oxypentyl)-benzoic acid methyl ester 
• 551-08-6 3-butylidenephthalide 
• 3413-15-8 butylphthalide 
• 131379-20-9 Ethyl o-(1-oxopentyl)benzoate 
• 1580457-30-2 2-(hex-1-en-2-yl)benzoic acid 

Relevant articles and documents

Preparation method of high-purity butylphthalide

The invention relates to a preparation method of high-purity butylphthalide. The preparation method comprises the following steps: (1) preparing n-butyl magnesium bromide; (2) synthesizing 2-valerylbenzoic acid; (3) synthesizing butylphthalide; and (4) refining the butylphthalide. Due to the adoption of the technical scheme, the preparation method has the advantages that the n-butyl magnesium bromide is used as an initiator in the step (1), so that the initiation condition is mild, and the safety performance is improved; and the initiation temperature is 38-42 DEG C, and the reaction temperature is only 48-52 DEG C, so that the temperature is easy to implement in the mass production process; the 2-valerylbenzoic acid is used as the raw material, and carbonyl is reduced in a sodium borohydride aqueous solution mode, so that explosion easily caused by a solid feeding mode is avoided, and production safety is guaranteed; and the butylphthalide is refined in a reduced pressure distillationmode, so that the method is simple and easy to implement, and the purity of the obtained high-purity butylphthalide reaches 100%. The synthesis process of butylphthalide is stable, the preparation process is mild and controllable, and the method is suitable for batch production.

A controllable bulk drug product and its preparation method

The present invention provides a butyl phthalide raw material drug product with the butyl phthalide content not less than 99.0%; the raw material drug is stable in quality, and can ensure the clinical curative effect and drug safety of a butyl phthalide preparation.

Preparation method of butylphthalide and pharmaceutical intermediate thereof

The present invention provides a new pharmaceutical intermediate and a method for preparing butylphthalide by using the new pharmaceutical intermediate. According to the method, o-phthalic acid monoester as a raw material and valerate are subjected to ester condensation, o-pentanoylbenzoic acid is prepared through hydrolysis and decarboxylation, and reducing with sodium borohydride and ring closure are performed to obtain the product. According to the present invention, the method has characteristics of inexpensive and easily-available raw material, mild reaction condition, no high-temperaturereaction, no Grignard reaction, production energy consumption reducing, production cost reducing and operation safety improving.

Ligustrazine-butyphthalide combination compound, preparation method of ligustrazine-butyphthalide combination compound, and application of ligustrazine-butyphthalide combination compound to pharmaceuticals

The invention discloses a ligustrazine-butyphthalide combination compound, a preparation method of the ligustrazine-butyphthalide combination compound and an application of the ligustrazine-butyphthalide combination compound to pharmaceuticals. The ligustrazine-butyphthalide combination compound has the following structural formula I as in the description. The phthalic anhydride and the ligustrazine are taken as starting materials, bromization, nucleophilic addition, catalytic dehydration, ester hydrolysis, reduction and esterification reactions are conduced to prepare the ligustrazine-butyphthalide combination compound; a pharmaceutical composition takes the ligustrazine-butyphthalide combination compound as an active pharmaceutical ingredient and is a pharmaceutically acceptable carrier, excipient, diluent, adjuvant, intermedium or a composition. The prepared ligustrazine-butyphthalide combination compound has an excellent effect of inhibiting in-vitro platelet aggregation (ADP) induced platelet aggregation, has a better in-vivo pharmacokinetics properties, and can be used for preventing and treating cardiovascular and cerebrovascular diseases, vascular senile dementia and the complications.

Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides

Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.

High-content butylphenyl phthaleine composition and preparation method thereof

The invention provides a high-content butylphenyl phthaleine composition. The butylphenyl phthaleine pharmaceutical composition comprises the following components: active component butylphenyl phthaleine, wherein the butylphenyl phthaleine content is no less than 99.5%; impurity with amount of no greater than 0.5% by metering weight percentage sum of butylphenyl phthaleine, wherein after placing for 24 months under normal condition, the butylphenyl phthaleine content is no less than 99.0%; and the impurity with amount of no greater than 1.0% by metering the weight percentage sum of butylphenyl phthaleine.

Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: Highly enantioselective and chemoselective access to a chiral benzylmethyl center

A carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins was developed by using a chiral spiro iridium catalyst, providing a highly efficient approach to the compounds with a chiral benzylmethyl center. The carboxy-directed hydrogenation prohibited the isomerization of the terminal olefins, and realized the chemoselective hydrogenation of various dienes. The concise enantioselective syntheses of (S)-curcudiol and (S)-curcumene were achieved by using this catalytic asymmetric hydrogenation as a key step.

NOVEL 2-(ALPHA-N-PENTANONYL)BENZOETES, THEIR PREPARATION AND USE

The present invention relates to novel compounds 2-(±-n-pentanonyl)benzoates, their preparation method, the pharmaceutical composition containing the same, and their use in preparing the medicament for preventing and treating cardio-cerebral ischemic disease, inhibiting thrombosis and alleviating the disturbance of cardio-cerebral circulation.

Stereoselective synthesis of 3-substituted phtalides via asymmetric transfer hydrogenation using well-defined ruthenium catalysts under neutral conditions

The asymmetric transfer hydrogenation of methyl 2-acylbenzoates and 2-propyl 3-acetylpyridine-2-carboxylate in 2-propanol, in the absence of base, with presynthesized Ru-{β-amino alcohol} or Ru-{TsDPEN} true catalysts provides 3-alkylphtalides in high yields and 92-97% ee. The procedure is, however, not as efficient for the preparation of optically active 3-phenylphtalide.

Microbial asymmetric syntheses of 3-alkylphthalide derivatives

Phthalide derivatives, almost all of which have an S-configuration, have a wide range of activity and exist in Angerica sinensis Diels and Sligusticum wallichiii Franch. For the first time, optically active (S)-3-methylphthalide derivatives were synthesized using two methods, asymmetric microbial reduction and microbial hydroxylation. For the first method, methyl 2-acetylbenzoate was synthesized as a substrate, which was reduced asymmetrically by Geotrichum candidum IFO 34614 to obtain (S)-3-methylphtalide in 92% yield (99% enantiomeric excess, ee). For the second method, 2-ethylbenzoic acid was employed as a substrate which was hydroxylated asymmetrically at the benzylic position by either Pseudomonas putida ATCC 12633 or Aspergillus niger IFO 6661, whose fermentation was induced by o-toluic acid, to obtain (S)-3-methylphthalide in 80% yield (99% ee). (S)-3-Butylphthalide and (S)-3-octylphthalide were obtained in the same manner in 12% yield (ee = 99%) and 10% yield (ee = 99%), respectively.