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3-Methoxysalicylaldehyde, also known as o-vanillin or 2-hydroxy-3-methoxybenzaldehyde in Chinese, is a compound with multiple uses and important chemical properties. The appearance is a light yellow needle shaped or fibrous solid, insoluble in cold water, slightly soluble in hot water, and soluble in most organic solvents such as ethanol, ether, chloroform, methanol, etc. It is a commonly used organic synthesis intermediate and has a wider range of applications in the synthesis of Schiff bases than vanillin. At the same time, it is also an effective antifungal agent that inhibits the growth of mycelium by disrupting the integrity of cell walls and membranes. It is used in the synthesis of various active pharmaceutical ingredients and is an important starting material for the synthesis of fragrances. It can also be used in industries such as electroplating. This substance can be extracted from vanillin and Pinus koraiensis fruit, and is also present in tobacco leaves, burley tobacco leaves, mainstream smoke, as well as natural substances such as vanilla beans, benzoin gum, Peruvian resin, and Tolugreek. Because it has certain toxicity and is harmful when swallowed. Do not eat, drink or smoke when using, and thoroughly wash your hands after handling. Wear personal protective equipment such as protective gloves, goggles, and masks. In case of accidental contact with skin, eyes or inhalation, appropriate first aid measures should be taken immediately and medical assistance should be sought.
Additional information of chemical compound:
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Chemical Formula |
C8H8O3 |
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Exact Mass |
152.05 |
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Molecular Weight |
152.15 |
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m/z |
152.05 (100.0%), 153.05 (8.7%) |
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Elemental Analysis |
C, 63.15; H, 5.30; O, 31.55 |
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Melting point |
40-42℃(lit.) |
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Boiling point |
265-266℃(lit.) |
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Density |
1.2143 (rough estimate) |
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Storage conditions |
Store below +30℃ |
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3-Methoxysalicylaldehyde, also known as o-vanillin or 2-hydroxy-3-methoxybenzaldehyde, is a chemical substance with a unique aroma and a wide range of uses. The following is a detailed explanation of its purpose:
In the synthesis of spices and essence
The o-vanillin itself is a high-quality spice, with a strong and lasting fragrance, which is very suitable for preparing various essence. In the spice industry, o-vanillin is often used as a basic spice, which combines with other spice ingredients to form essence products with unique fragrance. These essence products are widely used in food, cosmetics, daily necessities and other fields, adding rich colors and aroma to people's lives. It can also undergo chemical reactions with other spice components to synthesize composite spices with more complex aromas.
These composite spices perform well in terms of aroma layering and persistence, meeting consumers' demands for aroma diversity and persistence. For example, o-vanillin can react with alcohols, esters, ethers and other flavor components for esterification, condensation, etc. to produce esters, aldehydes, ketones and other compounds with unique aroma, which have extensive application value in the synthesis of essence. Its aroma is rich and long-lasting, effectively enhancing the aroma effects of other spices. In essence formula, appropriate addition of o-vanillin can significantly improve the aroma concentration and persistence of essence, making the product more attractive. In addition, the aroma of vanillin also has good blending properties, which can coordinate with other spice components to form a more harmonious aroma effect.
In the food industry, o-vanillin is one of the main raw materials for preparing vanilla essence. It can not only endow food with rich vanilla flavor, but also combine with other spice ingredients to form food essence with unique flavor. These essence are widely used in candy, cakes, drinks, condiments and other foods, adding rich aroma and taste to the food. For example, adding a moderate amount of vanillin to desserts such as chocolate and cream can make their aroma more rich and long-lasting, and their taste more delicate and rich. In daily chemical products, vanillin also has important application value.
It can be used to prepare various types of daily chemical essence, such as perfume, soap, shampoo, shower gel, etc. These essence can not only give daily chemical products unique fragrance, but also improve the quality and attractiveness of products. For example, in perfume, o-vanillin can be used as a fixative to make the fragrance more lasting and stable; In shampoo and shower gel, it can be combined with other fragrance ingredients to form products with a fresh aroma, enhancing the consumer experience. In the tobacco industry, o-vanillin is also widely used in the synthesis of tobacco essence. It can endow tobacco products with unique aroma and taste, improving the quality and attractiveness of tobacco products. In addition, vanillin can also mask the unpleasant odor in tobacco, making tobacco products softer and more pleasant.
The aroma of o-vanillin is rich and lasting, which is very suitable for preparing essence products that need to maintain the aroma for a long time. Its aroma has typical milk and vanilla notes, which can add unique aroma characteristics to the product. The chemical properties of vanillin are relatively stable and are not easily affected by external factors to deteriorate.
This enables it to maintain a stable aroma effect during the synthesis of spices and essence, and improve the quality and stability of the product. As a natural spice ingredient, its safety has been widely recognized. The use of essence products synthesized from o-vanillin in food, cosmetics, daily necessities and other industries will not cause harm to human health. This makes it have broad application prospects in these industries.
Antibacterial effect
As an effective antifungal agent, vanillin mainly achieves its antibacterial effect by disrupting the integrity of fungal cell walls and membranes. Specifically, it may exert antifungal effects through the following mechanisms:
Destruction of cell wall: The cell wall is an important structure of fungal cells, which has functions such as protecting cells, maintaining cell morphology, and osmotic pressure. Linvanillin can act on fungal cell walls, causing damage to the cell wall structure and thus disrupting its integrity.
This destructive effect makes fungal cells unprotected and vulnerable to external environmental attacks.
Disrupting the cell membrane: The cell membrane is the boundary between the internal and external environment of fungal cells, and has functions such as material transport and signal transduction. Linvanillin can also act on fungal cell membranes, disrupting their integrity and causing substances inside the cells to leak out, while harmful substances outside the cells enter, leading to cell death.
Impact on cellular metabolism: Linvanillin may also exert antifungal effects by affecting the metabolic processes of fungal cells. For example, it can inhibit the activity of certain enzymes within fungal cells, interfere with cellular metabolic pathways, and cause cell growth inhibition or death.
In vitro experiments, vanillin inhibited the hyphal growth of Aspergillus flavus in a dose-dependent manner. The inhibitory effect on Aspergillus flavus gradually increases with increasing concentration within the range of 0-125 μ g/mL.
This inhibitory effect lasts for 24-72 hours. 3-Methoxysalicylaldehyde can also alter the morphology of Aspergillus flavus hyphae, leading to irregular shrinkage of the hyphae. At the same time, it can also reduce the protein content and β -1,3-glucan content on the cell wall surface, further disrupting the integrity of the cell wall. In the experiment on corn kernels, vanillin also showed a significant inhibitory effect on the growth of Aspergillus flavus. It can effectively inhibit the growth of Aspergillus flavus on corn kernels within the concentration range of 0-100 μ g/mL.
In a mouse model, vanillin inhibits tumor growth in mice carrying A375 human melanoma xenografts through oral administration. This research result suggests that vanillin may have potential anti-tumor activity, but its specific mechanism still needs further investigation. Meanwhile, this also suggests that vanillin may have a certain inhibitory effect on other types of tumors.
Although the study primarily focused on the anti-tumor activity of vanillin, its results indirectly support the possibility of vanillin as an antifungal agent. Because tumor growth is often closely related to inflammatory response and immune regulation, vanillin can inhibit the activation of NF - κ B, which may help alleviate inflammatory response and regulate immune function, indirectly inhibiting fungal growth and spread.
As a natural product, vanillin has the advantages of low toxicity, high efficiency, and environmental friendliness. Therefore, it can serve as one of the candidate compounds for developing novel antifungal drugs. By modifying and optimizing its chemical structure, its antifungal activity can be further improved and toxicity reduced, thus developing safer and more effective antifungal drugs. Due to its significant inhibitory effect on various fungi, vanillin can be applied in the fields of food preservation and preservation.By adding it to food, it can effectively extend the shelf life of food and prevent the growth and reproduction of fungi. This can not only improve the quality and safety of food, but also reduce food waste and losses.
Application prospects in antifungal agents
Fungal diseases are one of the important factors affecting crop yield and quality in agricultural production. 3-Methoxysalicylaldehyde can be used as a biopesticide in agricultural production. Spraying or irrigating crops can effectively prevent fungal diseases and improve crop yield and quality. This can not only reduce the use of chemical pesticides and lower environmental pollution risks, but also enhance the market competitiveness of agricultural products. Linvanillin has the ability to inhibit NF - κ B activation, which makes it potentially valuable in the pharmaceutical and cosmetics industries. In the pharmaceutical industry, it can be used to develop drugs with anti-inflammatory, immune regulating and other functions; In the cosmetics industry, it can be used to develop cosmetics with antibacterial, moisturizing, antioxidant and other functions.
adverse reaction
3-Methoxysalicylaldehyde (CAS number: 148-53-8), chemical name 2-hydroxy-3-methoxybenzaldehyde, is an aromatic compound containing methoxy and aldehyde groups. Its molecular formula is C ₈ H ₈ O3, with a molecular weight of 152.15 g/mol. It is a solid powder at room temperature and may appear brown or light yellow. This substance is mainly used in organic synthesis, pharmaceutical intermediates, and the fragrance industry. Due to its adjacent hydroxyl and methoxy groups in its structure, it has potential biological activities such as antibacterial and antifungal properties.
Classification and mechanism of adverse reactions
Skin and mucosal irritation
Clinical manifestations: Contact may cause skin redness, itching, burning sensation, and even blisters; Eye contact can cause conjunctival congestion, tearing, and pain.
Mechanism: The chemical activity of aldehyde groups (- CHO) and phenolic hydroxyl groups (- OH) may disrupt cell membrane integrity and trigger inflammatory reactions.
Case support:
Sigma Aldrich's SDS clearly indicates its skin irritation level as Class 2 (H315) and eye irritation level as Class 2A (H319).
Animal experiments (Draize test) showed that rabbits showed significant irritation symptoms after 4 hours of eye contact.
Respiratory irritation
Clinical manifestations: Inhalation of dust or vapor may cause coughing, difficulty breathing, chest tightness, and long-term exposure may worsen chronic respiratory diseases.
Mechanism: Small molecule aldehydes are volatile and can directly irritate the respiratory mucosa upon inhalation, inducing neurogenic inflammation.
Case support:
Fisher Scientific's SDS lists its respiratory irritation level as H335 (may cause respiratory irritation).
Occupational exposure cases have shown that workers who do not wear protective equipment experience transient respiratory distress.
Digestive system reactions
Clinical manifestations: Ingestion may cause burning pain in the mouth, esophagus, and stomach, accompanied by nausea, vomiting, diarrhea, and in severe cases, may lead to gastrointestinal bleeding.
Mechanism: The strong irritant properties of aldehyde groups directly damage the gastrointestinal mucosa, and phenolic components may interfere with cellular metabolism.
Case support:
Sigma Aldrich's SDS labels its acute toxicity oral grade as Class 4 (H302), indicating harmful ingestion.
Animal experiments have shown that oral LD ₅₀ in mice is 1330 mg/kg, which is not highly toxic but still requires caution.
Potential systemic toxicity
Target organ toxicity: Long term or high-dose exposure may affect liver and kidney function, but the specific mechanism is not yet clear.
Ecotoxicity: It has acute toxicity to aquatic organisms (H411), indicating that it may affect the environment through bioaccumulation.
Case support:
Some SDS labels their specific target organ toxicity (STOT SE class 3), but lack detailed data.
Ecological research shows that its LC ₅₀ values for fish and algae are low, and attention should be paid to wastewater treatment.
Frequently Asked Questions
Is it the "twin brother" of vanillin? Does it smell like vanilla?
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Yes or no. It is a positional isomer of Vanillin, but with a completely different odor. Vanillin has a strong vanilla flavor, while vanillin has almost no fragrance and instead has a weak phenolic aroma, making it a "mute" in the spice industry. It is mainly used as a precursor for chemical reactions rather than as a fragrance enhancer.
Why is its pKa value so "clever"?
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Its phenolic hydroxyl pKa is 7.91. This value happens to be around physiological pH (7.4), indicating a dynamic equilibrium between protonation and deprotonation in the biological environment. This delicate balance allows it to penetrate membrane structures and form stable complexes with metal ions, which is a highly "spiritual" property in the eyes of medicinal chemists.
What hidden skills does it have as a "ligand"?
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It is an excellent ONO three toothed ligand skeleton. By condensing with amino acid derivatives or hydrazide, it can form complex Schiff base structures, which can then coordinate with transition metals such as vanadium oxide and molybdenum. These metal complexes have been found to be green catalysts for efficient synthesis of benzimidazole heterocycles, which are more environmentally friendly than traditional methods.
What tricks can it play with cobalt? What are the lesser known applications in materials?
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It can form a very stable octahedral complex with cobalt (II) [Co (3-OCH ∝ - salo) ₂ (bipy)]. It is interesting that this complex is stable in acetonitrile, but unstable in methanol and gradually oxidizes. This solvent dependent oxidation behavior makes it an ideal model compound for studying electron transfer and redox mechanisms.
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