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

• 28221-86-5 5-benzyloxy-3-methyl-benzofuran 
• 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 

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.

Application of cation-π interactions in enzyme-substrate binding: Design, synthesis, biological evaluation, and molecular dynamics insights of novel hydrophilic substrates for NQO1

Cation-π interaction is a type of noncovalent interaction formed between the π-electron system and the positively charged ion or moieties. In this study, we designed a series of novel NQO1 substrates by introducing aliphatic nitrogen-containing side chains to fit with the L-shaped pocket of NQO1 by the formation of cation-π interactions. Molecular dynamics (MD) simulation indicated that the basic N atom in the side chain of NQO1 substrates, which is prone to be protonated under physiological conditions, can form cation-π interactions with the Phe232 and Phe236 residues of the NQO1 enzyme. Compound 4 with a methylpiperazinyl substituent was identified as the most efficient substrate for NQO1 with the reduction rate and catalytic efficiency of 1263 ± 61 μmol NADPH/min/μmol NQO1 and 2.8 ± 0.3 × 106 M?1s?1, respectively. Notably, compound 4 exhibited increased water solubility (110 μg/mL) compared to that of β-lap (43 μg/mL), especially under acidic condition (pH = 3, solubility > 1000 μg/mL). Compound 4 (IC50/A549 = 2.4 ± 0.6 μM) showed potent antitumor activity against NQO1-rich cancer cells through ROS generation via NQO1-mediated redox cycling. These results emphasized that the application of cation-π interactions by introducing basic aliphatic amine moiety is beneficial for both the water solubility and the NQO1-substrate binding, leading to promising NQO1-targeting antitumor candidates with improved druglike properties.

Amide compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to amide compounds as shown by structural formula (I). The compounds are low absorbable TGR5 agonists and can be used to treat type II diabetes, obesity, liver or intestine chronic inflammatory diseases.