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

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

Uses

Used in Food Industry:
3-Methyl-5-Benzofuranol is used as a food flavoring agent for its sweet, caramel-like aroma, enhancing the taste and smell of a variety of food products. It is found naturally in fruits, vegetables, and roasted coffee beans, contributing to their distinct flavors.
Used in Fragrance Industry:
In the fragrance industry, 3-Methyl-5-Benzofuranol is used to add a sweet, caramel note to perfumes and personal care products, providing a rich and appealing scent.
Used in Natural Medicine:
3-Methyl-5-Benzofuranol has been studied for its potential health benefits, including antioxidant and anti-inflammatory properties. Its presence in natural foods and its potential medicinal properties make it a subject of interest in the field of natural medicine, with possible applications in developing health-promoting products.

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

Upstream product

• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 33038-04-9 ethyl 2-(2-acetyl-4-methoxyphenoxy)acetate 
• 33038-06-1 2-(2-acetyl-4-methoxyphenoxy)acetic acid 
• 7182-30-1 5-methoxy-3-methyl-1-benzofuran 
• 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.

MOR RECEPTOR AGONIST COMPOUND, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to the technical of medicinal chemistry, and specifically relates to a use of a 6-oxaspiro[4.5] decane derivative as an MOR receptor agonist for treating pain and pain-related disorders.

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.

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.

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.

A facile three-step total synthesis of tanshinone I

A facile synthetic approach for total synthesis of tanshinone I has been accomplished. The key precursor is a novel compound, epoxy phenanthraquinone. And this synthesis of tanshinone I is achieved in only three simple stages, which include Diels–Alder reaction, Δ2-Weitz–Scheffer-type epoxidation, and Feist–Bénary reaction from commercially available styrene.

3-methyl-benzofuran-5-ol and its use in perfume compositions

The present invention is directed to a novel fragrance compound, 3-methyl-benzofuran-5-ol, and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of 3-methyl-benzofuran-5-ol.

Antiandrogenic, maspin induction, and antiprostate cancer activities of tanshinone IIA and its novel derivatives with modification in ring A

Expression of metastatic suppressor maspin is lost in advanced prostate cancer. Clinically relevant mutations in androgen receptor (AR) convert antiandrogens into AR agonists, promoting prostate tumor growth. We discovered tanshinone IIA (TS-IIA) is a potent antagonist of mutated ARs and induces maspin expression through AR. TS-IIA suppressed AR expression and induced apoptosis in LNCaP cells. Syntheses of TS-IIA derivatives (1-9) revealed that the 4,4-dimethyl group at ring A is important for TS-IIA's antiandrogenic and maspin induction activities.

Synthesis, discovery and preliminary SAR study of benzofuran derivatives as angiogenesis inhibitors

A series of benzofuran derivatives were synthesized and evaluated against HUVEC proliferation. Among these compounds, compound 32 exhibited good inhibitory activity and remarkable selectivity to HUVEC. Our current data suggested that array order of methyl, acrylate and carboxylate groups in benzofuran scaffold is the basic requirement for inhibitory activity against HUVEC proliferation. These results demonstrated that benzofuran scaffold represents a promising structural core to discover a new class of active and selective angiogenesis inhibitors.