26358-19-0

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(4-HYDROXY-2-METHOXY-PHENYL)-ACRYLIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals. Its presence in these compounds can contribute to their therapeutic effects, potentially enhancing their efficacy and safety.
Used in Organic Chemistry:
As a building block in organic chemistry, 3-(4-HYDROXY-2-METHOXY-PHENYL)-ACRYLIC ACID is utilized in the creation of a wide range of organic compounds. Its versatile structure allows for various chemical reactions, facilitating the development of new molecules with different applications.
Used in Medical Applications:
3-(4-HYDROXY-2-METHOXY-PHENYL)-ACRYLIC ACID is used as a potential antioxidant and anti-inflammatory agent in medical applications. Its ability to combat oxidative stress and reduce inflammation can contribute to the treatment and management of various diseases and conditions.
Used in Cosmetic Applications:
In the cosmetic industry, 3-(4-HYDROXY-2-METHOXY-PHENYL)-ACRYLIC ACID is used for its potential antioxidant and anti-inflammatory properties. These benefits can help protect the skin from environmental damage and promote a healthier, more youthful appearance.
Used in Photodynamic Therapy:
3-(4-HYDROXY-2-METHOXY-PHENYL)-ACRYLIC ACID is being investigated for its potential use as a photosensitizer in photodynamic therapy for cancer treatment. Its ability to absorb light and generate reactive oxygen species could make it a valuable tool in the targeted destruction of cancer cells.

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 74-88-4 methyl iodide 
• 141-82-2 malonic acid 
• 18278-34-7 4-hydroxy-2-methoxybenzaldehyde 
• 1011-54-7 2-methoxycinnamic acid 
• 6972-61-8 2,4-dimethoxycinnamic acid 

Downstream Products

• 80754-26-3 ethyl 3-(4-hydroxy-2-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4

The cytochrome P450 enzyme, CYP199A4, demethylated 4-methoxybenzoic acid, but not 4-methoxyphenylacetic acid, with high product formation activity. The oxidative demethylation of 3-(4-methoxyphenyl)propionic acid was 8-fold more active than 4-methoxyphenylacetic acid and 4-methoxycinnamic acid was efficiently oxidised at a product formation rate of 180 nmol nmol-P450-1 min-1. Accordingly the oxidation of cinnamic acid derivatives was investigated in order to determine the potential of CYP199A4 to act as a biocatalyst for this important class of biological molecules. 4-Methoxy- and 4-methyl-cinnamic acids bound tightly to CYP199A4 and were better substrates for CYP199A4 than cinnamic acid itself. The oxidations of both 4-methoxy- and 4-methyl-cinnamic acids was 100% selective for attack at the para substituent. Certain dimethoxy substituted cinnamic acids were demethylated more efficiently than 4-methoxycinnamic acid and retained the selectivity for the para-methoxy substituent. Only very low product turnover was observed with 3,5-dimethoxycinnamic acid. 4-Isopropylcinnamic acid was hydroxylated and desaturated by CYP199A4 at the isopropyl group. Cinnamic acids with a para-substituted alkyl- and alkyloxy-cinnamic acid framework were a good fit for the active site of the CYP199A4 enzyme and as a consequence were efficiently and selectively oxidised. Whole-cell oxidations resulted in high yields of product and CYP199A4 could be developed for applications in the biocatalytic oxidation of cinnamic acid derivatives and related phenylpropanoids.

Non-natural cinnamic acid derivatives as substrates of cinnamate 4-hydroxylase

Cinnamate 4-hydroxylase (C4H), a monooxygenase in the plant phenylpropanoid pathway, was assayed for its ability to hydroxylate 29 substrate analogues. Nine of the tested analogues with various aromatic side chains, including 3-coumaric acid, were metabolized by C4H. Seven products from these reactive analogues were characterized using LC/MS, 1H NMR and 13C NMR spectroscopic analysis. For example, caffeic acid was the product of 3-coumaric acid. The products 4-hydroxy-2-chlorocinnamic acid and 4-hydroxy-2-ethoxycinnamic acid are novel compounds that have not been previously reported. The kinetic parameters of C4H towards these analogues were determined.

Preparation of vinylphenols from 2- and 4-hydroxybenzaldehydes

A straightforward, high-yielding procedure has been developed for the manufacture of substituted vinylphenols from 2- and 4-hydroxybenzaldehydes utilising classical Knoevenagel condensation reaction conditions.

ARYL SULFAMATE DERIVATIVES

The present invention provides an aryl sulfamate derivative represented by Formula (I) (wherein Rr and Rs, which may be the same or different, each represent a hydrogen atom or lower alkyl, R1, R2, R3

PHENYLALKANOIC ACID AND PHENYLOXYALKANOIC ACID DERIVATIVES AS HPPAR ACTIVATORS

The present invention provides a compound of formula (I):wherein:R1 and R2 are independently H or C1-3 alkyl;X represents a O or (CH2)n where n is 0, 1 or 2;R3and R4 independently represent H, C1-3 alkyl, -OCH3, -CF3, allyl, or halogen;X1 represents O, S, SO2, SO, or CH2;R5 and R6 independently represent hydrogen, C1-6 alkyl (including branched alkyl and optionally substituted by one or more halogens or C1-6alkoxy), or together with the carbon atom to which they are bonded form a 3-6 membered cycloalkyl ring;R7 represents a phenyl or a 6 membered heteroaryl group containing 1, 2 or 3 nitrogen atoms wherein the phenyl or heteroaryl group is substituted by 1, 2 or 3 moieties selected from the group consisting of halogen, C1-6 alkoxy, C1-6 alkyl, CF3, hydroxy, or phenyl (which may be optionally substituted by one or more C1-3 alkyl, -OC1-3 alkyl, CN, acetyl, hydroxy, halogen or CF3).