Veratraldehyde
[CAS# 120-14-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Aldehyde fragrance >> Aromatic aldehyde
• Name: Veratraldehyde
• Synonyms: Methylvanillin; Protocatechualdehyde dimethyl ether; Protocatechuic aldehyde dimethyl ether; Vanillin methyl ether; Veratric aldehyde; Veratrum aldehyde; Veratryl aldehyde; 3,4-Dimethoxy-benzaldehyde
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.18
• CAS Registry Number: 120-14-9
• EC Number: 204-373-2
• FEMA: 3109
• SMILES: COC1=C(C=C(C=C1)C=O)OC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 40-43 °C (Expl.)
• Index of Refraction: 1.534, Calc.^*
• Boiling Point: 281.0±0.0 °C (760 mmHg), Calc.^*, 281 °C (Expl.)
• Flash Point: 110.4±8.2 °C, Calc.^*, 113 °C (Expl.)
• Water solubility: <0.1 g/100 mL (22 °C)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Veratraldehyde is an aromatic aldehyde that belongs to the class of methoxy-substituted benzaldehydes. It exists in two isomeric forms, 3,4-dimethoxybenzaldehyde and 2,3-dimethoxybenzaldehyde, with the former being the more widely studied and applied. This compound appears as a pale yellow crystalline solid with a characteristic vanilla-like odor. It is known for its applications in the fragrance, pharmaceutical, and agrochemical industries, as well as its role as an intermediate in organic synthesis.

The discovery of veratraldehyde dates back to early research on natural and synthetic benzaldehydes. It is structurally related to vanillin, differing by an additional methoxy group. Veratraldehyde can be synthesized through the oxidation of veratryl alcohol or by formylation of veratrole using established organic chemistry methods. These synthetic approaches have been refined to achieve high purity and yield, making the compound readily available for industrial applications.

One of the primary applications of veratraldehyde is in the fragrance and flavor industry. Its pleasant, sweet aroma makes it a valuable ingredient in perfumes, food additives, and cosmetic formulations. It is used to enhance the scent profiles of various products and is sometimes employed as a substitute for vanillin in fragrance compositions.

In pharmaceuticals, veratraldehyde serves as a key intermediate in the synthesis of bioactive molecules. It is used in the preparation of certain antihypertensive and antifungal agents. The compound’s structural versatility allows for its modification into various derivatives with enhanced biological activity. Researchers have also explored its role in the development of drugs targeting neurological disorders and cardiovascular diseases.

Veratraldehyde is also utilized in agrochemical applications, particularly in the synthesis of plant growth regulators and pesticides. Its chemical properties make it a useful precursor for the development of bioactive compounds that improve crop protection and agricultural productivity. Additionally, it has been investigated for its antimicrobial properties, leading to potential applications in food preservation and surface coatings.

In material science, veratraldehyde is explored for its role in the preparation of polymers and advanced materials. It is used in the modification of resins and coatings to enhance durability and thermal stability. Its ability to participate in condensation reactions makes it an essential building block in the design of functional materials with tailored properties.

Safety considerations for veratraldehyde involve standard handling precautions. Although it has a low toxicity profile, direct exposure may cause irritation to the skin, eyes, or respiratory tract. Proper storage and handling are recommended to prevent degradation and ensure safe use in industrial and laboratory environments.

Future research on veratraldehyde focuses on expanding its applications in sustainable chemistry and green synthesis. Advances in biocatalysis and environmentally friendly synthetic routes aim to improve the efficiency and sustainability of its production. With its established role in various industries, veratraldehyde continues to be a valuable chemical for scientific and industrial applications.

References

2005. Methyl jasmonate modulated biotransformation of phenylpropanoids to vanillin related metabolites using Capsicum frutescens root cultures. Plant Physiology and Biochemistry: PPB.
DOI: 10.1016/j.plaphy.2005.01.006

2019. Degradation of the phenolic β-ether lignin model dimer and dyes by dye-decolorizing peroxidase from Bacillus amyloliquefaciens. Biotechnology Letters.
DOI: 10.1007/s10529-019-02696-0

2012. Combinatorial evaluation of laccase-mediator system in the oxidation of veratryl alcohol. Biotechnology Letters.
DOI: 10.1007/s10529-012-1078-1