4383-05-5

Basic information

• Product Name: 2-Hydroxy-3-methoxybenzyl alcohol
• Synonyms: 2-(Hydroxymethyl)-6-methoxyphenol;Benzenemethanol, 2-hydroxy-3-methoxy-;RARECHEM AL BD 0033;O-VANILLYL ALCOHOL;2-VANILLYL ALCOHOL;2-HYDROXY-3-METHOXYBENZYL ALCOHOL;3-methoxysalicyl alcohol;2-Hydroxy-3-methoxybenzenemethanol
• CAS NO: 4383-05-5
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16
• EINECS: 224-488-1
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 4383-05-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 135 °C0.2 mm Hg(lit.)
• Flash Point: 115.628 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1690 (rough estimate)
• Vapor Pressure: 8.98E-06mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 9.93±0.10(Predicted)
• CAS DataBase Reference: 2-Hydroxy-3-methoxybenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-3-methoxybenzyl alcohol(4383-05-5)
• EPA Substance Registry System: 2-Hydroxy-3-methoxybenzyl alcohol(4383-05-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 4383-05-5(Hazardous Substances Data)

Usage

Description

2-Hydroxy-3-methoxybenzyl alcohol, also known as vanillyl alcohol, is an organic compound with the chemical formula C8H10O3. It is a white to light yellow crystalline powder that is derived from natural sources such as lignin and certain plants. 2-Hydroxy-3-methoxybenzyl alcohol is characterized by its hydroxyl and methoxy groups, which contribute to its unique chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-3-methoxybenzyl alcohol is used as a substrate for the investigation of in vitro substrate specificity of enzymes, such as UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase from Sorghum bicolor (UGT85B1). This application is crucial in understanding the enzyme's role in the biosynthesis of various compounds and its potential use in drug development.
Used in Chemical Synthesis:
2-Hydroxy-3-methoxybenzyl alcohol serves as an important intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique functional groups make it a versatile building block for the development of new molecules with potential applications in various industries.
Used in Flavor and Fragrance Industry:
Due to its distinct aromatic properties, 2-Hydroxy-3-methoxybenzyl alcohol is used as a key component in the flavor and fragrance industry. It contributes to the development of natural and synthetic flavors for the food and beverage sector, as well as fragrances for the cosmetics and personal care products.
Used in Research and Development:
As a versatile organic compound, 2-Hydroxy-3-methoxybenzyl alcohol is employed in various research and development activities. It is used to study the structure-activity relationships of different molecules, explore novel chemical reactions, and develop new methodologies for organic synthesis.

InChI:InChI=1/C8H10O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-4,9-10H,5H2,1H3

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 195971-20-1 5-Fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(8-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 195885-82-6 1-[(2R,4S,5S)-4-Azido-5-(8-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 64-17-5 ethanol 
• 50-00-0 formaldehyd 
• 90-05-1 2-methoxy-phenol 
• 201165-99-3 4-Hydroxy-1-[(2R,5S)-5-(8-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-2,5-dihydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one 
• 877-22-5 3-methoxysalicylic acid 
• 6971-51-3 3-methoxybenzyl alcohol 
• 70882-23-4 8-methoxy-2-phenyl-4H-benzo[1,3,2]dioxaborinine 

Downstream Products

• 103447-33-2 2-acetoxymethyl-6-methoxyphenyl acetate 
• 42973-56-8 2-(2-hydroxy-3-methoxyphenyl)acetonitrile 
• 95062-50-3 C₈H₈O₂ 
• 1338675-76-5 C₅₄H₃₈N₄O₂Zn 
• 877-22-5 3-methoxysalicylic acid 
• 104265-19-2 ((1S,4aR,8aS)-7-Methoxy-8a-methoxymethyl-2-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid 
• 104199-10-2 ((1S,4aS,8aS)-7-Methoxy-8a-methoxymethyl-2-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid 
• 104199-16-8 ((1R,4aR,8aR)-7-Methoxy-8a-methoxymethyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid 
• 104199-09-9 ((1R,4aS,8aR)-7-Methoxy-8a-methoxymethyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl)-acetic acid 
• 104199-06-6 2-Methoxy-6-methoxymethyl-[1,4]benzoquinone 
• 104113-85-1 (4-Hydroxy-3-methoxy-5-methyl-phenyl)-acetonitrile 
• 104113-84-0 4-<(dimethylamino)methyl>-2-methoxy-6-methylphenol 
• 92367-72-1 (3,4-dimethoxy-5-methylphenyl)acetonitrile 
• 201165-99-3 4-Hydroxy-1-[(2R,5S)-5-(8-methoxy-2-oxo-4H-2λ⁵-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-2,5-dihydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one 

Relevant articles and documents

Asymmetric Retro-Claisen Reaction by Synergistic Chiral Primary Amine/Palladium Catalysis

We described herein a chiral primary amine/palladium catalyzed asymmetric retro-Claisen reaction of β-diketones with salicylic carbonates. A series of chiral α-alkylated ketones and macrolides were obtained with good yields and excellent enantioselectivities upon a sequence of decarboxylative benzylation, retro-Claisen cleavage, and enamine protonation. This strategy features broad substrate scope, mild conditions, as well as high atom economy with salicylic carbonates as the o-quinone methide precursors.

Photoresponsive azo-combretastatin A-4 analogues

Colchicine analogues in which an azo group is incorporated into a molecule containing the key pharmacophore of colchicine, have found particular utility as switchable tubulin binding chemotherapeutics. Combretastatin is a related compound containing a stilbene fragment that shows different bioactivity for the cis and trans isomers. We have performed cell assays on 17 new compounds structurally related to a previously reported azo-analogue of combretastatin. One of these compounds showed enhanced potency against HeLa (IC50 = 0.11 μM) and H157 cells (IC50 = 0.20 μM) for cell studies under 400 nm irradiation and the highest photoactivity (IC50 with irradiation/IC50 in dark = 550). We have performed docking and physicochemical studies of this new compound (7). Kinetic studies in water reveal a longer half-life for the cis isomer of 7 which may be one factor responsible for the better IC50 values in cell assays and the improved photoresponsive behavior.

Pd-catalyzed reduction of aldehydes to alcohols using formic acid as the hydrogen donor

Facile and selective reduction of aromatic aldehydes as well as aliphatic aldehydes to alcohols was achieved using formic acid as the hydrogen donor in the presence of a catalytic amount of Pd(OAc)2 and Cy3P. It was found that both hydrogen atoms in the formic acid molecule can serve as the hydride source. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]