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
• Article Data: 3

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

General Description

Alpha-guaiaconic acid is a chemical compound with the molecular formula C19H30O4. It is a natural product that can be found in plants such as Guaiacum officinale, a flowering plant native to the Caribbean and South America. Alpha-guaiaconic acid has been studied for its potential medicinal properties, including its antioxidant and anti-inflammatory effects. It is also used in organic synthesis and as a building block for the synthesis of other compounds. The compound is known for its unique chemical structure and has been the subject of research for its potential applications in pharmaceuticals and other industries.

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

• 61324-72-9 2,5-bis(4-benzyloxy-3-methoxyphenyl)-3,4-dimethylfuran 
• 61324-71-8 1,4-bis(4-benzyloxy-3-methoxyphenyl)-2,3-dimethylbutane-1,4-dione 
• 1835-16-1 1-(4-(benzyloxy)-3-methoxyphenyl)-2-bromopropan-1-one 
• 1835-15-0 1-(4-benzyloxy-3-methoxyphenyl)propan-1-one 
• 5438-66-4 1-(4-Benzyloxy-3-methoxy-phenyl)-propan-1-ol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 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 
• 60525-32-8 ethyl 3-[4-(benzyloxy)-3-methoxyphenyl]-3-oxopropanoate 
• 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.

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.