26509-45-5

Basic information

• Product Name: METHYLEUGENOLGLYCOL
• Synonyms: METHYLEUGENOLGLYCOL;1-(3,4-DIMETHOXYPHENYL)-2,3-PROPANEDIOL;3-(3,4-Dimethoxyphenyl)propane-1,2-diol
• CAS NO: 26509-45-5
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.27
• Mol File: 26509-45-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 67.5-69℃
• Boiling Point: 272.08°C (rough estimate)
• Flash Point: 184.5°C
• Appearance: /
• Density: 1.0204 (rough estimate)
• Vapor Pressure: 1.69E-06mmHg at 25°C
• Refractive Index: 1.4389 (estimate)
• CAS DataBase Reference: METHYLEUGENOLGLYCOL(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLEUGENOLGLYCOL(26509-45-5)
• EPA Substance Registry System: METHYLEUGENOLGLYCOL(26509-45-5)

Safety Data

• Hazardous Substances Data: 26509-45-5(Hazardous Substances Data)

Usage

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

Upstream product

• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 18523-76-7 (E)-3',4'-dimethoxycinnamyl alcohol 
• 70570-23-9 (Z)-3-(3,4-dimethoxyphenyl)-2-propen-1-ol 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 
• 54814-41-4 (+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 
• 188896-01-7 (Z)-3-(3,4-Dimethoxy-phenyl)-2-hydroxy-acrylic acid methyl ester 
• 27391-18-0 3'-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 
• 74-88-4 methyl iodide 
• 53940-49-1 2‐methoxy‐4‐(oxiran‐2‐ylmethyl)phenol 
• 38879-47-9 (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 143815-52-5 (Z)-3-(3,4-Dimethoxy-phenyl)-2-hydroxy-acrylic acid 
• 39829-15-7 methyl 3-(3,4-dimethoxyphenyl)oxirane-2-carboxylate 
• 27602-80-8 4-(2,3-epoxypropyl)-1,2-dimethoxybenzene 

Downstream Products

• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 47169-79-9 1,2-diacetoxy-3-(3,4-dimethoxy-phenyl)-propane 
• 142790-95-2 1-(3-chlorophenyl)-3-hydroxymethyl-6,7-dimethoxyisochromane 
• 1432494-09-1 (E)-ethyl 4-(3',4'-dimethoxyphenyl)but-2-enoate 
• 119030-66-9 (+/-)-isoarctigenin 
• 64767-71-1 (3R*,4R*)-3-(3,4-dimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 

Relevant articles and documents

Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.

Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zuba.

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