80489-90-3

Basic information

• Product Name: Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)-
• Synonyms: Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)-;2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid;Amorfrutin A
• CAS NO: 80489-90-3
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.41286
• Mol File: 80489-90-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 473.992 °C at 760 mmHg
• Flash Point: 161.575 °C
• Appearance: /
• Density: 1.159 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)-(80489-90-3)
• EPA Substance Registry System: Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)-(80489-90-3)

Safety Data

• Hazardous Substances Data: 80489-90-3(Hazardous Substances Data)

Usage

Description

Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethyl)is a complex organic compound with a unique molecular structure. It is characterized by the presence of a benzene ring, hydroxy, methoxy, and alkenyl groups, as well as a phenylethyl substituent. Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)has potential applications in various fields due to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethyl)is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure allows it to serve as a building block for the development of new therapeutic agents with potential applications in treating various diseases.
Used in Agrochemical Industry:
Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)is also used as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and functional groups make it a valuable component in the development of effective and targeted agrochemical products.
Used in Flavor and Fragrance Industry:
Due to its complex structure and potential aromatic properties, benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethyl)can be used as a starting material for the creation of unique flavors and fragrances. Its potential use in this industry could lead to the development of novel scents and tastes for various consumer products.
Used in Research and Development:
Benzoic acid, 2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-(2-phenylethyl)is also utilized in research and development settings, where it can be studied for its chemical properties, reactivity, and potential applications in various fields. Benzoic acid, 2-hydroxy-4-Methoxy-3-(3-Methyl-2-butenyl)-6-(2-phenylethyl)can serve as a valuable tool for scientists and researchers working on the development of new materials and technologies.

Upstream product

• 1416859-40-9 methyl 2-hydroxy-4-methoxy-6-(2-phenethyl)benzoate 
• 100-52-7 benzaldehyde 
• 1258410-99-9 (E)-2,4-dimethoxy-6-styrylbenzoic acid methyl ester 
• 1431610-36-4 ethyl 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoate 
• 1178567-20-8 2,4-dihydroxy-6-phenethyl-benzoic acid ethyl ester 
• 1431610-33-1 ethyl 2-hydroxy-4-methoxy-6-(2-phenylethyl)-benzoate 
• 1353896-19-1 7-methoxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one 
• 81574-69-8 2-bromo-4,6-dimethoxybenzaldehyde 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 1083433-29-7 2,4-dimethoxy-6-(2-phenylethyl)benzaldehyde 

Relevant articles and documents

A common building block for the syntheses of amorfrutin and cajaninstilbene acid libraries toward efficient binding with peroxisome proliferator-activated receptors

A common building block for the synthesis of amorfrutin and cajaninstilbene acid derivatives has been developed. The library of synthesized compounds has enabled identification of new nontoxic ligands of peroxisome proliferator-activated receptors (PPAR) and potential inhibitors of the transcriptional corepressor protein NCoR. The biological data holds promise in identification of new potential leads for the antidiabetic drug discovery process.

Biomimetic Total Syntheses of Amorfrutins A, B, (S)-D and (R)-D and Formal Synthesis of Amorfrutin C

Bibenzyl natural products, such as the amorfrutins, contain a heavily substituted aromatic core and display a diverse range of biological activities (anti-tumor, anti-diabetic, antimicrobial, and antibiotic). In this study, we report unified syntheses of amorfrutin A to D either through total or formal synthesis by employing a dual biomimetic strategy of polyketide aromatization followed by remote terpene functionalization. The key core structures were synthesized from β-keto dioxinone esters through a magnesium(II) mediated regioselective C-acylation, palladium catalyzed decarboxylative allylic rearrangement, and dehydrative cyclization.

An efficient and robust synthesis of amorfrutin A

Amorfrutin A was synthesized via a short sequence in an overall yield of 41% using a green, aerobic oxidation/re-arrangement process as the key-step.