20133-19-1

Basic information

• Product Name: 1-(3,4-Dimethoxyphenyl)-1,2-propanediol
• Synonyms: 1-(3,4-Dimethoxyphenyl)-1,2-propanediol;1-(3,4-Dimethoxyphenyl)propane-1,2-diol;Methyl isoeugenol glycol
• CAS NO: 20133-19-1
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.2423
• Mol File: 20133-19-1.mol

Chemical Properties

• Boiling Point: 382.2°Cat760mmHg
• Flash Point: 184.9°C
• Appearance: /
• Density: 1.162g/cm³
• Vapor Pressure: 1.6E-06mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(3,4-Dimethoxyphenyl)-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-Dimethoxyphenyl)-1,2-propanediol(20133-19-1)
• EPA Substance Registry System: 1-(3,4-Dimethoxyphenyl)-1,2-propanediol(20133-19-1)

Safety Data

• Hazardous Substances Data: 20133-19-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(3,4-Dimethoxyphenyl)-1,2-propanediol is utilized as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural features that facilitate the creation of diverse medicinal compounds.
Used in Organic Chemistry as a Reagent:
In the realm of organic chemistry, DMPD serves as a valuable reagent, contributing to a range of chemical reactions that require its specific functional groups for successful synthesis.
Used in Antioxidant and Anti-inflammatory Research:
1-(3,4-Dimethoxyphenyl)-1,2-propanediol is studied for its potential antioxidant properties, which could be harnessed to combat oxidative stress in biological systems. Additionally, its anti-inflammatory effects are of interest, potentially offering therapeutic benefits in conditions characterized by inflammation.
Used in Anticancer Research:
DMPD has been investigated for its ability to inhibit the growth of certain cancer cells, suggesting a possible role in oncology. Its mechanism of action and potential as a therapeutic agent in cancer treatment are areas of active research, with the aim of developing novel cancer therapies.
While the specific applications and industries for DMPD are not explicitly detailed in the provided materials, the above uses are inferred from its described properties and areas of study. Further research is necessary to fully understand and validate the potential applications and effects of 1-(3,4-Dimethoxyphenyl)-1,2-propanediol.

InChI:InChI=1/C11H16O4/c1-14-10-4-3-8(5-11(10)15-2)9(6-12)7-13/h3-5,9,12-13H,6-7H2,1-2H3

Upstream product

• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 93-16-3 Methylisoeugenol 

Downstream Products

• 93-07-2 Veratric acid 
• 64-19-7 acetic acid 
• 4732-70-1 3,4-dimethoxyphenylglyoxylic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 58045-92-4 1,2-diacetoxy-1-(3,4-dimethoxy-phenyl)-propane 

Relevant articles and documents

Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin

Methylisoeugenol (1,2-dimethoxy-4-propenylbenzene, 1) is a minor constituent of essential oils, naturally occurring as a mixture of cis/trans isomers. 1 is a U.S. Food and Drug Administration-approved food additive and has been given "Generally Recognized as Safe" status. Previously, metabolism of 1 has been studied in the rat, revealing mainly nontoxic cinnamoyl derivatives as major metabolites. However, data concerning the possible formation of reactive intermediary metabolites are not available to date. In this study, the oxidative metabolism of 1 was studied using liver microsomes of rat [not induced, rat liver microsomes (RLM); Aroclor1254 induced RLM (ARLM)], bovine, and human (pooled from 150 donors) origin. Incubations of these microsomes with 1 provided phase I metabolites that were separated by high-performance liquid chromatography (HPLC) and identified by NMR and UV-visible spectroscopy and/or liquid chromatography-mass spectrometry. Identity was confirmed by comparison with 1H NMR spectra of synthesized reference compounds. Formation of metabolites was quantified by HPLC/UV using dihydromethyleugenol (10) synthesized as the internal standard. From incubations of ARLM with 1, seven metabolites could be detected, with 3′- hydroxymethylisoeugenol (2), isoeugenol and isochavibetol (3 + 4), and 6-hydroxymethylisoeugenol (5) being the main metabolites. Secondary metabolites derived from 1 were identified as the α,β-unsaturated aldehyde 3′-oxomethylisoeugenol (6) and 1′,2′-dihydroxy- dihydromethylisoeugenol (7). We were surprised to find that formation of allylic 6-hydroxymethyleugenol (8) was observed starting at approximately 30 min after the beginning of incubations with ARLM. HLM did not form ring-hydroxylated metabolites but were most active in the formation of 6 and 7. ARLM incubations displayed the highest turnover rate and broadest metabolic pattern, presumably resulting from an increased expression of cytochrome P450 enzymes. In conclusion, we present a virtually complete pattern of nonconjugated microsomal metabolites of 1 comprising reactive metabolites and suggest the formation of reactive intermediates that need more investigation with respect to their possible adverse properties. Copyright

Synthesis of aromatic aldehydes by laccase-mediator assisted oxidation

Aromatic aldehydes can be prepared in aqueous medium by oxidation of the corresponding methyl aromatic compounds in the presence of oxygen, the enzyme laccase and catalytic amounts of various N-hydroxy compounds. Allylic alcohols also gave the corresponding aldehydes in good yield. Competing reactions reveal that the N-hydroxy compound is involved in the rate determining step of the reaction.

Electron-transfer Processes: Oxidation of α- and β-Alkenylbenzenes by Peroxydisulphate in Acetic Acid

Oxidation of α- and β-unsaturated alkylbenzenes by peroxydisulphate in acetic acid gives side-chain acetoxylation with formation of the corresponding glycol diacetates and compounds (10), respectively.The reaction is catalysed by transition-metal salts, among which cupric acetate gives the best results.Generally, electron-releasing substituents on the benzene ring increase the yield and improve the selectivity.The same substrates are oxidized in water under Ag+ catalysis to the corresponding aldehydes.The different behaviour in the two solvents is ascribed to the difference in reactivity between the primary oxidation products and the starting olefin, whereas the initial oxidation step is suggested to occur in both cases via an electron-transfer process from the olefin to the sulphate radical anion.