3,4-Dimethoxybenzyl alcohol
[CAS# 93-03-8]

Identification

• Classification: Chemical pesticide >> Insecticide >> Organophosphorus pesticide
• Name: 3,4-Dimethoxybenzyl alcohol
• Synonyms: Veratryl alcohol
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.19
• CAS Registry Number: 93-03-8
• EC Number: 202-212-0
• SMILES: COC1=C(C=C(C=C1)CO)OC

Properties

• Density: 1.157 g/mL (25 ºC)
• Melting point: 22 ºC
• Boiling point: 296-297 ºC (732 mmHg)
• Refractive index: 1.552
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H318
• Precautionary Statements: P264-P264+P265-P270-P280-P301+P317-P305+P354+P338-P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

3,4-Dimethoxybenzyl alcohol is an organic compound classified as a substituted benzyl alcohol, where two methoxy (–OCH₃) groups are located at the 3- and 4-positions of the aromatic ring. It has the molecular formula C₉H₁₂O₃ and appears as a colorless to pale yellow liquid or solid, depending on the purity and storage conditions. This compound is structurally related to vanillyl alcohol and belongs to a broader class of phenethyl derivatives that include natural products and synthetic intermediates of pharmacological relevance.

The discovery and early identification of 3,4-dimethoxybenzyl alcohol stemmed from studies on lignin degradation products and the metabolism of aromatic compounds in plants and microorganisms. It has been found as a trace component in the biosynthetic or metabolic pathways of certain plant species, particularly in the context of aromatic amino acid metabolism, such as that of tyrosine. The presence of the 3,4-dimethoxy substitution pattern is also common in a variety of naturally occurring phenylpropanoids and lignin-derived compounds.

Synthetic routes to 3,4-dimethoxybenzyl alcohol are well established. One common method involves the reduction of 3,4-dimethoxybenzaldehyde using standard hydride reagents such as sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). This reduction proceeds cleanly to form the corresponding primary alcohol. Other approaches may include Grignard-type reactions starting from 3,4-dimethoxybenzyl halides or related protected derivatives. These synthetic protocols are routinely used in laboratory and industrial settings, where the compound serves as a building block for more complex molecules.

In terms of application, 3,4-dimethoxybenzyl alcohol is widely utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and fine chemicals. It serves as a precursor for various substituted aromatic compounds, including amines, aldehydes, esters, and ethers. The compound is often employed in protecting group strategies, where the benzyl group is used to mask reactive hydroxyl functionalities during multi-step synthesis and later removed under reductive conditions.

Its methoxy-substituted aromatic ring imparts specific electronic properties, making it a useful scaffold in the development of bioactive molecules. Several derivatives of 3,4-dimethoxybenzyl alcohol have been investigated for their antimicrobial, antifungal, and anticancer activities, often as part of larger molecules containing pharmacophores that target biological receptors or enzymes. It also appears in the synthesis of compounds that act as monoamine oxidase inhibitors and other enzyme modulators in medicinal chemistry.

In polymer and material science, 3,4-dimethoxybenzyl alcohol can be employed as a monomer or chain stopper in the formulation of specialty polymers and resins. Its aromatic core provides rigidity, while the hydroxyl functionality allows for incorporation into ester, urethane, or ether linkages. These characteristics are beneficial in designing polymers with specific thermal or mechanical properties.

Analytically, the compound can be identified and quantified using techniques such as nuclear magnetic resonance (NMR) spectroscopy, gas chromatography-mass spectrometry (GC-MS), and high-performance liquid chromatography (HPLC). Its well-defined chemical shifts and fragmentation patterns make it a reliable standard or reference compound in qualitative and quantitative assays.

Environmental and toxicological studies have indicated that 3,4-dimethoxybenzyl alcohol has relatively low acute toxicity and limited persistence in the environment. Its metabolic fate in biological systems generally involves oxidation of the benzylic alcohol to the corresponding aldehyde and acid, followed by conjugation and excretion. Biodegradation studies suggest that microbial populations can effectively break down this compound under aerobic conditions.

3,4-Dimethoxybenzyl alcohol continues to be a valuable compound in both academic research and industrial applications, owing to its chemical versatility, functional group compatibility, and role as an intermediate in the synthesis of a wide range of biologically and chemically significant molecules.

References

1993. Lignin peroxidase L3 from Phlebia radiata. Pre-steady-state and steady-state studies with veratryl alcohol and a non-phenolic lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol. European Journal of Biochemistry, 211(3).
DOI: 10.1111/j.1432-1033.1993.tb17562.x

1998. Nitration of Veratryl Alcohol by Lignin Peroxidase and Tetranitromethane. Archives of Biochemistry and Biophysics, 352(1).
DOI: 10.1006/abbi.1997.0570

2005. Expression on wood, molecular cloning and characterization of three lignin peroxidase (LiP) encoding genes of the white rot fungus Phlebia radiata. Current Genetics, 49(2).
DOI: 10.1007/s00294-005-0045-y