5703-24-2

Basic information

• Product Name: 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde
• Synonyms: 3-Methoxy-4-hydroxyphenylacetaldehyde;(4-hydroxy-3-methoxyphenyl)acetaldehyde;3-Methoxy-4-hydroxybenzeneacetaldehyde;4-Hydroxy-3-methoxybenzeneacetaldehyde;Benzeneacetaldehyde, 4-hydroxy-3-methoxy-;Hmpal
• CAS NO: 5703-24-2
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.1739
• Mol File: 5703-24-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 310.5 °C at 760 mmHg
• Flash Point: 126.4 °C
• Appearance: /
• Density: 1.17 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde(5703-24-2)
• EPA Substance Registry System: 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde(5703-24-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5703-24-2(Hazardous Substances Data)

Usage

General Description

2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is a chemical compound with a molecular formula of C9H10O3. It is a white crystalline solid that is slightly soluble in water but soluble in organic solvents. 2-(4-hydroxy-3-methoxy-phenyl)acetaldehyde is a key intermediate in the biosynthesis of the pigment melanin and is also involved in various metabolic pathways in plants and animals. It is commonly found in a variety of natural sources, such as fruits, vegetables, and medicinal plants, and is also used as a flavoring agent in the food and beverage industry. The compound has also been studied for its potential antioxidant and anti-inflammatory properties. However, it should be handled with care, as it may pose health risks if not used properly.

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

• 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 
• 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 

Relevant articles and documents

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.

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.