7417-21-2

Basic information

• Product Name: 2-(3,4-Dimethoxyphenyl)ethanol
• Synonyms: AKOS 222-31;3,4-DIMETHOXYPHENETHYL ALCOHOL;3,4-DIAMETHOXYBENZYL METHANOL;1-(2-Hydroxyethyl)-3,4-dimethoxybenzene;2-(3,4-Dimethoxyphenyl)ethanol;3,4-Dimethoxy-beta-phenethyl alcohol;3,4-Dimethoxyphenethanol;Benzeneethanol, 3,4-dimethoxy-
• CAS NO: 7417-21-2
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• EINECS: 231-032-5
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 7417-21-2.mol

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 172-174 °C17 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Light yellow/Crystalline Powder
• Density: 1.0966 (rough estimate)
• Vapor Pressure: 0.000702mmHg at 25°C
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.80±0.10(Predicted)
• BRN: 909742
• CAS DataBase Reference: 2-(3,4-Dimethoxyphenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-Dimethoxyphenyl)ethanol(7417-21-2)
• EPA Substance Registry System: 2-(3,4-Dimethoxyphenyl)ethanol(7417-21-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 7417-21-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2-(3,4-Dimethoxyphenyl)ethanol is used as a model compound for studying the delignification mechanism of Mn(III)-substituted polyoxometalates (MSP). Its role in these studies aids in understanding the complex processes involved in the breakdown of lignin, which is a crucial component in the production of paper and biofuels.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-(3,4-Dimethoxyphenyl)ethanol, given its structural similarity to various bioactive compounds, could potentially be used in the pharmaceutical industry as a starting material for the synthesis of drugs targeting specific receptors or enzymes.
Used in Material Science:
The light yellow crystalline nature of 2-(3,4-Dimethoxyphenyl)ethanol suggests that it may have applications in material science, particularly in the development of novel materials with specific optical or electronic properties.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 8, p. 266, 1960 DOI: 10.1248/cpb.8.266

InChI:InChI=1/C10H14O3/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7,11H,5-6H2,1-2H3

Upstream product

• 10597-60-1 hydroxytyrosol 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 15964-79-1 methyl (3,4-dimethoxyphenyl)acetate 
• 91-16-7 1,2-dimethoxybenzene 
• 406215-61-0 1,2-dimethoxy-4-(2-tert-butyldimethylsiloxyethyl)benzene 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 196081-78-4 3-bromo-4-hydroxyphenylethyl alcohol 
• 2380-78-1 homovanillyl alcohol 
• 74-88-4 methyl iodide 
• 64-17-5 ethanol 
• 18066-68-7 ethyl 3,4-dimethoxyphenylacetate 
• 109-72-8 n-butyllithium 
• 2859-78-1 4-Bromoveratrole 

Downstream Products

• 75010-39-8 1-(3,4-dimethoxyphenyl)-2-(p-toluenesulfonyloxy)ethane 
• 19084-86-7 4-(3,4-dimethoxy-phenethyloxy)-1H-benzo[d][1,2]oxazine 
• 86970-86-7 3-(3,4-dimethoxy-phenethyl)-5-methyl-oxazolidine-2,4-dione 
• 86106-19-6 3-<2-(3,4-dimethoxyphenyl)ethyl>-5,5-dimethylthiazolidine-2,4-dione 
• 86633-27-4 2-(3,4-dimethoxyphenyl)ethyl α-ethoxyethyl ether 
• 22506-58-7 3,4-dihydro-6,7-dimethoxy-1-phenyl-1H-2-benzopyran 
• 92774-37-3 6,7-dimethoxy-1-(3-methoxyphenyl)isochroman 
• 92774-36-2 1-(2-methoxyphenyl)-6,7-dimethoxyisochroman 
• 187940-01-8 1-(4'-bromophenyl)-6,7-dimethoxyisochroman 
• 187940-02-9 4-(3,4-dihydro-6,7-dimethoxy-1H-isochromen-1-yl)benzonitrile 
• 192525-15-8 N-[2-(trimethylsilyl)ethyloxycarbonyl]-N-(allyloxy)-2-(3,4-dimethoxyphenyl)ethylamine 
• 193689-57-5 2-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-trifluoromethanesulfonyl-amino}-3-methyl-butyric acid ethyl ester 
• 193689-58-6 {[2-(3,4-Dimethoxy-phenyl)-ethyl]-trifluoromethanesulfonyl-amino}-phenyl-acetic acid ethyl ester 
• 193689-59-7 {[2-(3,4-Dimethoxy-phenyl)-ethyl]-trifluoromethanesulfonyl-amino}-phenyl-acetic acid benzyl ester 

Relevant articles and documents

Biotransformation of pungent constituents from ginger (Zingiber officinale Roscoe) by Colletotrichum gloeosporioides yields oxidative ortho–ortho coupling products

This work investigated the biotransformation of ginger constituents (zingerone, [6]-shogaol, [6]-gingerol, and methyl-[6]-gingerol) by the pathogenic fungus Colletotrichum gloeosporioides. Experiments were carried out with and without deuterium-labelled compounds. The product metabolites were analyzed by liquid chromatography coupled to tandem mass spectrometry and liquid chromatography solid phase extraction-nuclear magnetic resonance. Substrates supplied to the fungus were incorporated into metabolic pathways mostly by oxidation reactions, including aromatic carbon–carbon coupling. Zingerone and [6]-gingerol biotransformation products included biphenol dimers. A biodegradation pathway for biphenol formation was proposed based on the presence of the intermediate 4-(2-hydroxyethyl)-2-methoxyphenol, commonly identified from [6]-gingerol and [6]-shogaol biodegradation. This intermediate likely originates from a Baeyer–Villiger reaction followed by hydrolysis. The C–C coupling of molecules could result in phenolic oxidative ortho–ortho coupling, suggesting that biphenol dimers are products of C. gloeosporioides laccase catalysis.

Total synthesis of three natural phenethyl glycosides

Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

Tetrabenazine intermediate as well as synthesis method and application thereof as, well as intermediate product for synthesis (by machine translation)

The invention belongs to, the field of drug synthesis, and particularly relates to a butanaphenazine, intermediate and a synthesis method, thereof, as well as a synthesis: method 3,4 - thereof; and, 6,7 . (by machine translation)

Structure-Activity Relationship Study Enables the Discovery of a Novel Berberine Analogue as the RXRα Activator to Inhibit Colon Cancer

We reported recently that berberine (Ber), a traditional oriental medicine to treat gastroenteritis, binds and activates retinoid X receptor α (RXRα) for suppressing the growth of colon cancer cells. Here, we extended our studies based on the binding mode of Ber with RXRα by design, synthesis, and biological evaluation of a focused library of 15 novel Ber analogues. Among them, 3,9-dimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium chloride (B-12) was identified as the optimal RXRα activator. More efficiently than Ber, B-12 bound and altered the conformation of RXRα/LBD, thereby suppressing the Wnt/β-catenin pathway and colon cancer cell growth via RXRα mediation. In addition, B-12 not only preserved Ber's tumor selectivity but also greatly improved its bioavailability. Remarkably, in mice, B-12 did not show obvious side effects including hypertriglyceridemia as other RXRα agonists or induce hepatorenal toxicity. Together, our study describes an approach for the rational design of Ber-derived RXRα activators as novel effective antineoplastic agents for colon cancer.

BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY

The present invention relates to novel bio-inspired hybrid compounds of formula I which act as proteasome activators and exhibit anti-ageing activity, as well as methods for their synthesis. These hybrid compounds combine the structural features of hydroxytyrosol and the natural antioxidant vitamin E or its bioisosteres in one molecular scaffold. The compounds of formula I, which include structural proteasome activators (activation by stereochemical interaction), can be used in the production of anti-ageing products, such as cosmetic preparations. Additionally, they can be used in conditions and diseases where the proteasome is down-regulated, as well as proteasome-activation control compounds.

Fibrauretine synthetic method (by machine translation)

The invention relates to O-vanillin (11) as the starting material, by the acylation reaction generating 2 - acetoxy - 3 - methoxybenzaldehyde (12), by the bromo, hydrolysis reaction to produce the 2 - hydroxy - 6 - bromo - 3 - methoxybenzaldehyde (13), produced by the methylation reaction 6 - bromo - 2, 3 - dimethoxy benzaldehyde (14), produced by the condensation reaction of 2 - (6 - bromo - 2, 3 - dimethoxyphenyl) - 1, 3 - dioxolane (15); and then to 3, 4 - dimethoxy acetic acid (21) as raw materials, generated by the reduction reaction of the 3, 4 - dimethoxy ethanol (22), the acylation reaction generated by 3, 4 - dimethoxy new valeric acid environmentally (23), the acylation reaction is generated by the 2 - ethoxy - 3, 4 - dimethoxy new valeric acid environmentally (24), intermediate (15) and (24) after coupling, cyclized two-step reaction process for preparing the target product fibrauretin. (by machine translation)

Harnessing open-source technology for low-cost automation in synthesis: Flow chemical deprotection of silyl ethers using a homemade autosampling system

An inexpensive homemade 3-axis autosampler was used to facilitate the automation of an acid catalysed flow chemical desilylation reaction. Harnessing open-source software technologies (Python, OpenCV), an automated computer-vision controlled liquid-liquid extraction step was used to provide effective inline purification. A Raspberry Pi single-board computer was employed to interface with the motors used in the autosampler and actuated fluidic valves.

Synthesis and Biological Evaluation of N-[2-(4-Hydroxyphenylamino)-pyridin-3-yl]-4-methoxy-benzenesulfonamide (ABT-751) Tricyclic Analogues as Antimitotic and Antivascular Agents with Potent in Vivo Antitumor Activity

Benzopyridothiadiazepine (2a) and benzopyridooxathiazepine (2b) were modified to produce tricyclic quinazolinone 15-18 or benzothiadiazine 26-27 derivatives. These compounds were evaluated in cytotoxicity and tubulin inhibition assays and led to potent inhibitors of tubulin polymerization. N-[2(4-Methoxyphenyl)ethyl]-1,2-dihydro-pyrimidino[2,1-b]quinazolin-6-one (16a) exhibited the best in vitro cytotoxic activity (GI50 10-66.9 nM) against the NCI 60 human tumor cell line and significant potency against tubulin assembly (IC50 0.812 μM). In mechanism studies, 16a was shown to block cell cycle in G2/M phase and to disrupt microtubule formation and displayed good antivascular properties as inhibition of cell migration, invasion, and endothelial tube formation. Compound 16a was evaluated in C57BL/6 mouse melanoma B16F10 xenograft model to validate its antitumor activity, in comparison with reference ABT-751 (1). Compound 16a displayed strong in vivo antitumor and antivascular activities at a dose of 5 mg/kg without obvious toxicity, whereas 1 needed a 10-fold higher concentration to reach similar effects.

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.

Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines

A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.