53172-10-4

Basic information

• Product Name: dehydroparadol
• Synonyms: dehydroparadol
• CAS NO: 53172-10-4
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.37066
• Mol File: 53172-10-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 423.2°Cat760mmHg
• Flash Point: 148.4°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 9.25E-08mmHg at 25°C
• Refractive Index: 1.538
• CAS DataBase Reference: dehydroparadol(CAS DataBase Reference)
• NIST Chemistry Reference: dehydroparadol(53172-10-4)
• EPA Substance Registry System: dehydroparadol(53172-10-4)

Safety Data

• Hazardous Substances Data: 53172-10-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h9-13,19H,3-8H2,1-2H3/b11-9+

Upstream product

• 821-55-6 2-Nonanone 
• 121-33-5 vanillin 
• 881-68-5 vanillin acetate 

Downstream Products

• 27113-22-0 [6]-paradol 

Relevant articles and documents

6-SHOGAOL DERIVATIVES AND ACTIVITIES THEREOF

Derivatives of 6-shogaol are described herein. Also described herein are methods of preparing the derivatives, as well as methods of using the derivatives to activate Nrf2 and to treat diseases associated with inflammation and/or oxidative stress.

Synthesis, evaluation, and metabolism of novel [6]-shogaol derivatives as potent Nrf2 activators

Oxidative stress is a central component of many chronic diseases. The Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2 p45-related factor 2 (Nrf2) system is a major regulatory pathway of cytoprotective genes against oxidative and electrophilic stress. Activation of the Nrf2 pathway plays crucial roles in the chemopreventive effects of various inducers. In this study, we developed a novel class of potent Nrf2 activators derived from ginger compound, [6]-shogaol (6S), using the Tg[glutathione S-transferase pi 1 (gstp1):green fluorescent protein (GFP)] transgenic zebrafish model. Investigation of structure-activity relationships of 6S derivatives indicates that the combination of an α,β-unsaturated carbonyl entity and a catechol moiety in one compound enhances the Tg(gstp1:GFP) fluorescence signal in zebrafish embryos. Chemical reaction and in vivo metabolism studies of the four most potent 6S derivatives showed that both α,β-unsaturated carbonyl entity and catechol moiety act as major active groups for conjugation with the sulfhydryl groups of the cysteine residues. In addition, we further demonstrated that 6S derivatives increased the expression of Nrf2 downstream target, heme oxygenase-1, in both a dose- and time-dependent manner. These results suggest that α,β-unsaturated carbonyl entity and catechol moiety of 6S derivatives may react with the cysteine residues of Keap1, disrupting the Keap1-Nrf2 complex, thereby liberating and activating Nrf2. Our findings of natural product-derived Nrf2 activators lead to design options of potent Nrf2 activators for further optimization.