5703-24-2

Usage

Uses

Used in Flavoring Agents:
2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is used as a flavoring agent in the food and beverage industry for its distinctive aromatic properties, enhancing the sensory experience of various products.
Used in Pharmaceutical and Nutraceutical Industries:
In the pharmaceutical and nutraceutical sectors, 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is utilized for its potential antioxidant and anti-inflammatory properties, contributing to the development of health supplements and medicinal formulations.
Used in Cosmetics Industry:
2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is also employed in the cosmetics industry, where it may be incorporated into formulations to leverage its antioxidant properties for skin health and protection.
Used in Research and Development:
2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is used as a key intermediate in research and development for the study of melanin biosynthesis and its role in various biological processes, potentially leading to advancements in understanding pigmentation disorders and related conditions.

Upstream product

• 7786-61-0 3-methoxy-4-hydroxystyrene 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2380-78-1 homovanillyl alcohol 
• 91471-08-8 3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 91471-09-9 2-(2-Methoxy-4-oxiranyl-phenoxy)-tetrahydro-pyran 
• 7382-68-5 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 854733-85-0 4-indol-3-yl-2-methoxy-phenol 
• 13033-77-7 (4-hydroxy-3-methoxy-phenyl)-acetaldehyde-semicarbazone 
• 86200-91-1 (4-hydroxy-3-methoxy-phenyl)-acetaldehyde-oxime 
• 2380-78-1 homovanillyl alcohol 
• 172546-95-1 (R)-(-)-<6>-2,2-difluoro-4,4-(1,3-propanedithioacetyl)gingerol-t-butyldimethylsilylether 
• 172546-92-8 (S)-(+)-<6>-2,2-difluoro-4,4-(1,3-propanedithioacetyl)gingerol-t-butyldimethylsilylether 
• 172546-96-2 (S)-(+)-<6>-2,2-difluorogingerol-t-butyldimethylsilylether 
• 172546-93-9 (S)-(-)-<6>-2,2-difluorogingerol-t-butyldimethylsilylether 
• 785725-14-6 2-Methoxy-4-(2-phenethylamino-ethyl)-phenol 
• 172547-01-2 (4-hydroxy-3-methoxyphenyl)ethylaldehyde propanedithioacetal 

Relevant academic research and scientific papers

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

METHOD FOR BIOCATALYTIC SYNTHESIS OF SUBSTITUTED OR UNSUBSTITUTED PHENYLACETIC ACIDS AND KETONES HAVING ENZYMES OF MICROBIAL STYRENE DEGRADATION

The present invention relates to a method for the biocatalytic synthesis of substituted and unsubstituted phenylacetic acids and ketones from styrenes and bicyclic aromatic hydrocarbons using enzymes of microbial styrene degradation in a whole-cell sensor, as well as a kit for the biocatalytic synthesis of substituted and unsubstituted phenylacetic acids and ketones containing a whole-cell catalyst and the use of the method, wherein the method comprises the following steps: a) providing at least one type of whole-cell catalyst, containing genes which code for the enzymes of styrene degradation and are under the functional control of a regulatable promoter, in an aqueous component,b) activating the whole-cell catalyst with an inducer and/or an activator, leading to expression of the gene,c) bringing the activated whole-cell catalyst into contact with a substrate,d) isolating the reaction products produced, which are advantageously not further metabolized by the whole-cell cat and advantageously accumulate in the aqueous component.

The catalytic potential of Coptis japonica NCS2 revealed - Development and utilisation of a fluorescamine-based assay ETI

The versatility and potential of a norcoclaurine synthase (NCS) from Coptis japonica NCS2 has been investigated, together with the development and application of a novel fluorescence-based high-throughput assay using nearly forty amines/aldehydes. The stereocontrol exerted by CjNCS2 on selected non-natural substrates has been determined, where the tetrahydroisoquinolines (THIAs) were formed as the (1S)-isomer in >95% ee, as observed with the natural product norcoclaurine. Docking calculations involving THIA mechanism intermediates, utilising the reported Thalictrum flavum NCS X-ray crystallographic structure, were carried out and combined with the CjNCS2 screening results to further understand the mode of action of NCS. These findings suggested that in addition to the key active-site residues K122 and E110, D141 is also mechanistically essential for the enzymatic transformation. The exceptional tolerance of NCS towards aldehyde substrates is furthermore supported by our proposed mechanism in which the aldehydes protrude out of the enzymatic pocket. Copyright

PROCESS FOR PREPARING HYDROXYTYROSOL

A process for preparing hydroxytyrosol from eugenol is disclosed. The eugenol can be converted to 4-(2-hydroxyethyl)-2-methoxyphenol, which is subsequently converted to hydroxytyrosol. The eugenol can also be initially demethylated, and the reaction product is subsequently converted to hydroxytyrosol. A process for producing 4-(2-hydroxyethyl)-2-methoxyphenol is also disclosed.

Methoxyphenols from burning of Scandinavian forest plant materials

Semivolatile compounds in smoke from gram-scale incomplete burning of plant materials were assessed by gas chromatography and mass spectrometry. Gas syringe sampling was shown to be adequate by comparison with adsorbent sampling. Methoxyphenols as well as 1,6-anhydroglucose were released in amounts as large as 10 mg kg-1 of dry biomass at 90% combustion efficiency. Wood, twigs, bark and needles from the conifers Norway spruce and Scots pine emitted 12 reported 2-methoxyphenols in similar proportions. Grass, heather and birchwood released the same 2-methoxyphenols but also the corresponding 2,6-dimethoxyphenols which are characteristic of angiosperms. The methoxyphenols are formed from lignin and differ in structure by the group in para position relative to the phenolic OH group. Prominent phenols were those with trans-l-propenyl and ethenyl groups in that position. Vanillin, 4- hydroxy-3-methoxybenzaldehyde, was a prominent carbonyl compound from the conifer materials. (C) 2000 Elsevier Science Ltd.

Synthesis of chiral difluorinated [6]-gingerol

Total synthesis of chiral difluorinated [6]-gingerol using key intermediates (R)-(+)-and (S)-(-)-ethyl 2,2-difluoro-3-hydroxyoctanoates, obtained via enzymatic resolution with olipase/4S (Rhizopus japonicus) is described. Copyright

A Convenient Strategy for Homologation of p-Oxygenated Benzaldehydes

It is shown that p-oxygenated benzaldehydes can be conveniently obtained by pyrolysis of the corresponding oxiranes.