Vanillic Acid CAS 121-34-6 | Look Chemical

Vanillic acid can be mainly used in the synthesis of flavors or medicines, such as 5-nitrovanillic acid, which can be used as a 3,5-disubstituted catechol catechol-O-methyltransferase (COMT-I) inhibitor. The synthesis of tolcapone, or as a precursor for the biosynthesis of rifamycin antibiotics (3-hydroxymethoxyrifamycin, 3-hydroxyrifamycin).

Vanillic acid is one of the active ingredients in plants such as vanilla beans, vanilla pods, and Coptidis Coptidis. It has antibacterial, anti-inflammatory, antioxidant, tyrosinase inhibitory, allelopathic, nerve-regulating, and procoagulant activities at home and abroad. All of them have been studied to a certain extent, have good activity, and have good market prospects. Examples of its applications are as follows:

1. Used in the synthesis of vanillin. Vanillin, also known as vanillin, has a chemical name of 3-methoxy-4-hydro xybenzaldehyde. It is a broad-spectrum high-end spice, known as the king of spices, and is widely used in food, beverages, spices, medicine and other fields. The annual consumption is very large, and most of the products are chemically synthesized. Pure natural products are mainly extracted from vanilla pods, and the output is very small, which is far from meeting the market demand.
2. Use microorganisms to transform natural precursors to produce natur-identical (NI) vanillin, called “biovanillin”, which can replace natural vanillin. The specific method is to screen out a strain of Pycnoporus vermilion SW-0203 that can transform vanillic acid into vanillin. After optimizing the culture medium and transformation conditions, it can convert 1.682 g/L vanillic acid into 0.875 g/L vanillin. Aldehyde, molar conversion rate is 57.5%. A scale-up test was conducted on a 25 L tank, and the vanillin yield was 0.818 g/L, and the molar conversion rate was 53.7%. The product in the conversion solution was extracted to obtain vanillin crystals with a purity of 95% and an extraction yield of 63.9%.
3. In addition, some studies have used enzyme kinetics methods to study the inhibitory effect of vanillic acid on the monophenolase and diphenolase activities of tyrosinase. The results show that vanillic acid has an inhibitory effect on the monophenolase and diphenolase activities of tyrosinase. All have inhibitory effects, and the vanillic acid concentration (IC50) that causes a 50% decrease in monophenolase activity and diphenolase activity is approximately 1. 3 mmol /L and 2. 6 mmol /L respectively.
4. Vanillic acid can significantly prolong the lag time of monophenolase. 2 mmol/L vanillic acid can extend the lag time from 1.1 min to 4.7 min. The inhibitory effect of vanillic acid on diphenolase is mixed inhibition, and the inhibition constant (KI) of the free enzyme and the inhibition constant (KIS) of the enzyme-substrate complex are 1. 76 mm o l /L and 8, respectively. . 57 mmol/L.
5. In addition, there are studies to explore the autotoxic effects of the phenolic acid autotoxic substance vanillic acid, study its effects on peanut seed germination and seedling growth, and reveal the response patterns of rhizosphere soil microorganisms to autotoxic substances during the peanut growth period.