27391-18-0

Usage

InChI:InChI=1/C10H14O4/c1-14-10-5-7(2-3-9(10)13)4-8(12)6-11/h2-3,5,8,11-13H,4,6H2,1H3

Upstream product

• 57371-42-3 4-allyl-1-benzyloxy-2-methoxybenzene 
• 97-53-0 4-allylguaiacol 
• 53940-49-1 2‐methoxy‐4‐(oxiran‐2‐ylmethyl)phenol 

Downstream Products

• 54844-36-9 3-(3,4-dimethoxyphenyl)propane-1,2-diol 
• 54910-32-6 (R)-3-3(3,4-dimethoxyphenyl)propane-1,2-diol 

Relevant academic research and scientific papers

Synthesis of four eugenol metabolites

Four eugenol metabolites were concisely synthesized and their structures were confirmed by1H-NMR,13C-NMR and high-resolution mass (HR-MS). Among them, the synthesis of eugenol-β-D-glucuronide (3) and eugenol sulfate (4) was reported for the first time. The successful synthesis of the four eugenol metabolites provides a material basis for further metabolic study of prodrug aspirin euge-nol ester (AEE).

NOVEL 1-PHENYLMONO- OR -POLYHYDROXYPROPANE COMPOUNDS, COMPOSITIONS AND COSMETIC USES THEREOF

The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.

Phenolic derivatives from the stems of Lagerstroemia indica and their biological activity

The purification of a MeOH extract from the stems of Lagerstroemia indica (Lythraceae) using repeated column chromatography afforded three new phenolic glycosides (1-3), and a new flavone derivative (4) along with fifteen known compounds (5-19). The structures of new compounds were determined through spectral analysis, including 1D, 2D-NMR and MS data. Compounds 1-19 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line and cytotoxic activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15).

Synthesis and evaluation of antiproliferative activity of a novel series of hydroxychavicol analogs

We have recently demonstrated that hydroxychavicol is a major constituent and the most active biophenolic of Piper betel leaves with significant antiproliferative activity in the micro molar range. Herein we present the design, synthesis and evaluation of fifteen novel hydroxychavicol analogs with varying antiproliferative activities in cancer cell lines from two representative tissue types, namely, the prostate and cervix that show very encouraging results compared to the parent compounds. Our long range goal is to develop a structure-activity guided relationship to gain mechanistic insights into novel molecular targets of this class of bioactive molecules for rational drug development. Cytotoxicity-guided experimentation on these novel analogs yielded the following structural factors as the key activity regulators: 1) unlike the hydroxyl substituent at position-4, the position-3 hydroxyl is vital for enhanced activity 2) acetoxyl groups are dispensable for activity as corroborated earlier by others 3) allylic double bonds at 2′C-3′C serve to positively influence antiproliferative activity 4) long saturated side chains at 1′-position negatively regulate antiproliferative activity and 5) maneuvering position-4 with a benzyl group positively impacted the biological activity profile. Most amphiphilic compounds showed moderate to good therapeutic potential as expected on the basis of medicinal chemistry principles. Intriguingly, the most active compound with ten-fold higher activity than the parent molecule was realized by sheer serendipity to employ a silica gel based rearrangement that was further explored using nuclear magnetic resonance spectroscopy and density functional theory calculations. This is the first report to describe strategies for optimal synthesis of a novel series of 15 analogs based upon hydroxychavicol, a simple phytochemical of immense anticancer potential.

Antioxidative phenylpropanoids from berries of Pimenta dioica

A phenylpropanoid, threo-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane- 1,2-diol, was isolated from the berries of Pimenta dioica together with five known compounds, eugenol, 4-hydroxy-3-methoxycinnamaldehyde, 3,4- dimethoxycinnamaldehyde, vanillin and 3-(4-hydroxy-3-methoxyphenyl)propane- 1,2-diol. In addition, the stereochemistry of 3-(4-hydroxy-3- methoxyphenyl)propane-1,2-diol was determined. The phenylpropanoids inhibited autoxidation of linoleic acid in a water-alcohol system.