3598-26-3

Basic information

• Product Name: 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol
• Synonyms: 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol;3,4-Dihydroxycinnamyl alcohol;Caffeic alcohol
• CAS NO: 3598-26-3
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.1739
• Mol File: 3598-26-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 393.1 °C at 760 mmHg
• Flash Point: 202.1 °C
• Appearance: White solid
• Density: 1.331 g/cm³
• CAS DataBase Reference: 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol(3598-26-3)
• EPA Substance Registry System: 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol(3598-26-3)

Safety Data

• Hazardous Substances Data: 3598-26-3(Hazardous Substances Data)

Usage

General Description

4-(3-Hydroxy-1-propen-1-yl)-1,2-benzenediol is a chemical compound with the molecular formula C9H10O3. It is also known as 4-(3-hydroxyallyl)-pyrocatechol and is a derivative of pyrocatechol. 4-(3-Hydroxy-1-propen-1-yl)-1,2-benzenediol is a phenolic compound and is commonly found in various plants and fruits, where it serves as a natural antioxidant and pigment. It has been studied for its potential antioxidant and anti-inflammatory properties, as well as for its potential role in preventing and treating various diseases. Additionally, it is also used in the production of various pharmaceuticals, fragrances, and other industrial products.

Upstream product

• 331-39-5 caffeic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 121-33-5 vanillin 
• 3843-74-1 Methyl caffeate 
• 100976-84-9 ethyl 3,4-diacetoxycinnamate 
• 74257-25-3 ethyl caffeate 

Downstream Products

• 366493-18-7 isoamericanol A 
• 119280-58-9 americanol A 
• 74708-36-4 (7'E)-(7α,8β)-3,4,9-trihydroxy-3',7-epoxy-8,4'-oxyneolign-7'-en-9'-al 
• 458-35-5 coniferol 
• 533929-76-9 C₁₀H₁₁O₃ 
• 72898-29-4 4-propenylcatechol 
• 1126-61-0 4-allylpyrocatechol 
• 46118-02-9 3-(3',4'-dihydroxyphenyl)-1-propanol 

Relevant articles and documents

Microbial Production of Natural and Unnatural Monolignols with Escherichia coli

Phenylpropanoids and phenylpropanoid-derived plant polyphenols find numerous applications in the food and pharmaceutical industries. In recent years, several microbial platform organisms have been engineered towards producing such compounds. However, for the most part, microbial (poly)phenol production is inspired by nature, so naturally occurring compounds have predominantly been produced to date. Here we have taken advantage of the promiscuity of the enzymes involved in phenylpropanoid synthesis and exploited the versatility of an engineered Escherichia coli strain harboring a synthetic monolignol pathway to convert supplemented natural and unnatural phenylpropenoic acids into their corresponding monolignols. The performed biotransformations showed that this strain is able to catalyze the stepwise reduction of chemically interesting unnatural phenylpropenoic acids such as 3,4,5-trimethoxycinnamic acid, 5-bromoferulic acid, 2-nitroferulic acid, and a “bicyclic” p-coumaric acid derivative, in addition to six naturally occurring phenylpropenoic acids.

A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism

Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.

A novel and efficient procedure for the preparation of allylic alcohols from α,β-unsaturated carboxylic esters using LiAlH4/BnCl

A new and efficient method for the reduction of α,β-unsaturated carboxylic esters to allylic alcohols utilizing LiAlH4/BnCl is described. Various α,β-unsaturated esters, including the coumarins bearing α,β-unsaturated lactone skeleton, can be converted smoothly into their corresponding allylic alcohols in high yields under mild conditions with short reaction times.