7182-21-0

Basic information

• Product Name: 3-Methyl-5-Benzofuranol
• Synonyms: 3-Methyl-5-Benzofuranol;5-Benzofuranol, 3-methyl-;3-methylbenzofuran-5-ol
• CAS NO: 7182-21-0
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.15862
• Mol File: 7182-21-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 92 °C
• Boiling Point: 272.7 °C at 760 mmHg
• Flash Point: 118.7 °C
• Appearance: /
• Density: 1.223 g/cm³
• Vapor Pressure: 0.0036mmHg at 25°C
• Refractive Index: 1.63
• PKA: 9.46±0.40(Predicted)
• CAS DataBase Reference: 3-Methyl-5-Benzofuranol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-5-Benzofuranol(7182-21-0)
• EPA Substance Registry System: 3-Methyl-5-Benzofuranol(7182-21-0)

Safety Data

• Hazardous Substances Data: 7182-21-0(Hazardous Substances Data)

Usage

General Description

3-Methyl-5-benzofuranol, also known as "homofuraneol," is a chemical compound with a sweet, caramel-like odor. It is commonly used as a food flavoring agent and is found naturally in a variety of foods, including fruits, vegetables, and roasted coffee beans. 3-Methyl-5-benzofuranol is also a major contributor to the aroma of maple syrup and is often used in the fragrance industry to add a sweet, caramel note to perfumes and personal care products. The compound has also been studied for its potential health benefits, including antioxidant and anti-inflammatory properties, making it a subject of interest in the field of natural medicine.

InChI:InChI=1/C9H8O2/c1-6-5-11-9-3-2-7(10)4-8(6)9/h2-5,10H,1H3

Upstream product

• 7182-30-1 5-methoxy-3-methyl-1-benzofuran 
• 33038-06-1 2-(2-acetyl-4-methoxyphenoxy)acetic acid 
• 33038-04-9 ethyl 2-(2-acetyl-4-methoxyphenoxy)acetate 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 20521-59-9 1-(N-morpholino)-prop-1-ene 
• 106-51-4 p-benzoquinone 
• 7647-01-0 hydrogenchloride 
• 113297-22-6 3-methyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-ol 
• 1356255-04-3 C₁₄H₁₇NO₂ 
• 7182-09-4 N-(1-propenyl)piperidine 
• 857554-49-5 (2-acetyl-4-benzyloxy-phenoxy)-acetic acid 
• 857554-47-3 (2-acetyl-4-benzyloxy-phenoxy)-acetic acid ethyl ester 
• 30992-63-3 5-benzyloxy-2-hydroxyacetophenone 
• 28221-86-5 5-benzyloxy-3-methyl-benzofuran 

Downstream Products

• 28221-86-5 5-benzyloxy-3-methyl-benzofuran 
• 568-73-0 Tanshinone I 
• 77769-21-2 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione 
• 96839-29-1 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione 
• 96839-30-4 (±)-tanshindiol C 
• 96839-30-4 (+)-(3S,4S)-tanshindiol C 
• 96839-30-4 tanshindiol C 
• 96894-91-6 (+)-(3R,4S)-tanshindiol B 
• 97465-70-8 tanshindiol B 

Relevant articles and documents

2-Substituted 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-diones as specific L-shaped NQO1-mediated redox modulators for the treatment of non-small cell lung cancer

Based on the scaffold of 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione, a series of L-shaped derivatives with substituted side chains at the position of C2 were designed by analyzing the binding mode with NQO1. The drug-like compound 6q (named as DDO-7178) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by one-electron oxidoreductases CPR (NQO1/CPR = 20.8). In addition, compound 6q showed much improved physicochemical properties such as water solubility than the control β-lap. The follow-up studies indicated that 6q showed a NQO1-expressing cancer-cell-selective killing property. Preliminary mechanism studies on the anticancer effect indicated that 6q induced ROS production in an NQO1 dependent manner and activated Akt/MAPK pathways in a ROS-dependent fashion, thereby inducing apoptosis. In addition, emphasized compound 6q showed more significant antitumor efficacy than β-lap without producing obvious toxic effects in vivo, which gave us a new tool for further investigation of NQO1-mediated redox modulators as anticancer drugs for the treatment of NQO1-overexpressed NSCLC.

Three-Step One-Pot Process of 3-Methyl-5-Benzofuranol from Amine, Aldehydes, and p-Benzoquinone

3-Methyl-5-benzofuranol was prepared by a one-pot process from morpholine, propionaldehyde, and p-benzoquinone in 85-87% isolated yields. Avoiding the tedious multistep isolation and purification operations, this practical and efficient process dramatically enhanced the production efficiency as well as reduced the amount of chemical wastes of reaction. The scale-up results showed that the performance was maintained, suggesting potential large-scale applications. Furthermore, the synthesis strategy showed high efficiency for a wide range of aliphatic aldehydes and ketone derivatives.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.