10035-27-5

Basic information

• Product Name: alpha-guaiaconic acid
• Synonyms: alpha-guaiaconic acid;2,5-Bis(4-hydroxy-3-methoxyphenyl)-3,4-dimethylfuran;4,4'-(3,4-Dimethyl-2,5-furandiyl)bis(2-methoxyphenol);Furoguaiacin
• CAS NO: 10035-27-5
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.3698
• Mol File: 10035-27-5.mol

Chemical Properties

• Boiling Point: 435.1°Cat760mmHg
• Flash Point: 217°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 3.52E-08mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: alpha-guaiaconic acid(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-guaiaconic acid(10035-27-5)
• EPA Substance Registry System: alpha-guaiaconic acid(10035-27-5)

Safety Data

• Hazardous Substances Data: 10035-27-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Alpha-guaiaconic acid is used as a medicinal compound for its potential antioxidant and anti-inflammatory effects, which can contribute to the development of treatments for various health conditions.
Used in Organic Synthesis:
Alpha-guaiaconic acid is used as a building block in organic synthesis, enabling the creation of other compounds that can have diverse applications in different industries.
Used in Research and Development:
Due to its unique chemical structure, alpha-guaiaconic acid is used in research and development for exploring its potential applications in pharmaceuticals and other industries, with the aim of discovering new uses and enhancing existing ones.

InChI:InChI=1/C20H20O5/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)25-19(11)13-5-7-15(21)17(9-13)23-3/h5-10,21-22H,1-4H3

Upstream product

• 60525-32-8 ethyl 3-[4-(benzyloxy)-3-methoxyphenyl]-3-oxopropanoate 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 5438-66-4 1-(4-Benzyloxy-3-methoxy-phenyl)-propan-1-ol 
• 1835-15-0 1-(4-benzyloxy-3-methoxyphenyl)propan-1-one 
• 1835-16-1 1-(4-(benzyloxy)-3-methoxyphenyl)-2-bromopropan-1-one 
• 61324-71-8 1,4-bis(4-benzyloxy-3-methoxyphenyl)-2,3-dimethylbutane-1,4-dione 
• 61324-72-9 2,5-bis(4-benzyloxy-3-methoxyphenyl)-3,4-dimethylfuran 
• 121-33-5 vanillin 
• 159211-06-0 2,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-furan-3,4-dicarboxylic acid diethyl ester 
• 96931-98-5 diethyl 2,3-bis-(4-benzyloxy-3-methoxybenzoyl)butane-1,4-dioate 
• 203383-29-3 3'-methoxy-4'-methylsulfonyloxypropiophenone 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 203383-32-8 2,5-bis(3-methoxy-4-methylsulfonyloxyphenyl)-3,4-dimethylfuran 
• 202844-41-5 [2,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-4-hydroxymethyl-furan-3-yl]-methanol 

Downstream Products

• 131829-51-1 4,4'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(2-methoxyphenol) 
• 10039-58-4 2,5-bis-((Ξ)-3-methoxy-4-oxo-cyclohexa-2,5-dienylidene)-3,4-dimethyl-2,5-dihydro-furan 

Relevant articles and documents

Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin

1-Arylnaphthalene lignans such as (-)-isoguaiacin and (-)-isogalbulin have been reported to exhibit notable biological properties. While (-)-isoguaiacin has not been previously synthesized, syntheses of (-)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.

Preparations of Furans from α-Bromo Ketones and Enol Ethers Catalyzed by a Rhenium(I) Nitrogen Complex

By the catalytic use of a rhenium(I) nitrogen complex, [ReCl(N2)(PMe2Ph)4], α-keto radicals are generated from α-bromo ketones and react with vinyl ethers and silyl enol ethers intermolecularly. Various substituted furans, including tetrasubstituted furans such as furoguaiacin, are prepared by this method.

A novel synthetic route to furan-lignans

Three naturally occurring furan-lignans and two analogs have been synthesized by a short and efficient route starting from the corresponding aryl acid. The selective reductive removal of allylic hydroxy by palladium oxide in a mixed solvent of THF-CHCl3 was employed as the key step.