Ethyl vanillin - 121-32-4
Ethyl vanillin
Catalog Number: BT-253233
CAS Number: 121-32-4
Molecular Formula: C9H10O3
Molecular Weight: 166.17 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Ethyl vanillin is a synthetic flavoring agent that is commonly used in the food industry. It is a white to yellow crystalline powder with a sweet, vanilla-like odor and taste. Ethyl vanillin is a derivative of vanillin, which is the primary component of natural vanilla extract. Ethyl vanillin is used as a substitute for natural vanilla extract due to its lower cost and greater stability.
Properties
CAS Number
121-32-4
Product Name
Ethyl vanillin
IUPAC Name
3-ethoxy-4-hydroxybenzaldehyde
Molecular Formula
C9H10O3
Molecular Weight
166.17 g/mol
InChI
InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3
InChI Key
CBOQJANXLMLOSS-UHFFFAOYSA-N
SMILES
CCOC1=C(C=CC(=C1)C=O)O
Solubility
Slightly soluble (NTP, 1992)
0.02 M
2.82 mg/mL at 25 °C
In water, 2,822 mg/L at 25 °C
Slightly soluble in water (1 g in 100 mL at 50 °C)
Soluble in ethanol, ether, benzene, chloroform
Freely soluble in ... solutions of alkali hydroxides; soluble in glycerol, propylene glycol
Solubility in 95% alcohol about 1 g/2 mL
insoluble in water; soluble in organic solvents, oils
very soluble (1g in 2ml) (in ethanol)
Synonyms
3-ethoxy-4-hydroxybenzaldehyde
ethyl vanillin
Canonical SMILES
CCOC1=C(C=CC(=C1)C=O)O
Method of Synthesis or Extraction
Ethyl vanillin is typically synthesized from guaiacol and ethylvanillin using various methods. The most commonly used method is the Friedel-Crafts acylation reaction, which involves the reaction of guaiacol with ethyl chloride in the presence of a Lewis acid catalyst, such as aluminum chloride. The reaction yields ethyl vanillin with a high efficiency and yield. However, this method has environmental and safety considerations due to the use of toxic and corrosive reagents.
Another method of synthesizing ethyl vanillin is through the use of microbial biotransformation. This method involves the use of microorganisms, such as bacteria and fungi, to convert guaiacol into ethyl vanillin. This method has the advantage of being more environmentally friendly and safer than the Friedel-Crafts acylation reaction. However, the efficiency and yield of this method are lower than the Friedel-Crafts acylation reaction.
Chemical Structure and Biological Activity
The chemical structure of ethyl vanillin is similar to that of vanillin, with the addition of an ethyl group. Ethyl vanillin has been shown to have biological activity, including antioxidant, antimicrobial, and anti-inflammatory properties. The mechanism of action of ethyl vanillin is thought to involve the inhibition of reactive oxygen species and the modulation of various signaling pathways.
Biological Effects
Ethyl vanillin has been shown to have potential therapeutic effects on various cell functions and signal transduction pathways. It has been studied for its potential use in the treatment of cancer, diabetes, and neurodegenerative diseases. However, ethyl vanillin also has potential toxic effects, including cytotoxicity and genotoxicity. Further research is needed to fully understand the potential therapeutic and toxic effects of ethyl vanillin.
Applications
Ethyl vanillin has a wide range of applications in various fields, including medical research, environmental research, and industrial research. In medical research, ethyl vanillin has been studied for its potential role in drug development and clinical trials. It has been shown to have potential benefits in the treatment of various diseases, including cancer and diabetes. However, potential side effects and toxicity must be carefully considered.
In environmental research, ethyl vanillin has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have potential sustainability and environmental impact, particularly in the food industry. In industrial research, ethyl vanillin is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations must be carefully considered in the use of ethyl vanillin in industrial applications.
Future Perspectives and Challenges
The use and study of ethyl vanillin face several limitations and challenges. These include the potential toxicity and side effects, as well as the need for further research to fully understand the biological activity and mechanism of action. Possible solutions and improvements include the development of safer and more efficient methods of synthesis and extraction, as well as the development of new applications and uses for ethyl vanillin. Future trends and prospects in the application of ethyl vanillin in scientific research include the continued study of its potential therapeutic effects and its role in the food industry.
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