33171-16-3

Basic information

• Product Name: (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione
• Synonyms: (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione
• CAS NO: 33171-16-3
• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.35
• Mol File: 33171-16-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 571.4 °C at 760 mmHg
• Flash Point: 205.5 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 1.17E-13mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione(33171-16-3)
• EPA Substance Registry System: (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione(33171-16-3)

Safety Data

• Hazardous Substances Data: 33171-16-3(Hazardous Substances Data)

Usage

General Description

The chemical "(1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione" is a compound with a molecular structure of C19H14O5. It is a polyphenolic compound containing two hydroxyphenyl groups and a hepta-1,6-diene-3,5-dione backbone. (1E,6E)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di ene-3,5-dione has potential antioxidant and anti-inflammatory properties due to the presence of hydroxyphenyl groups, which are known for their ability to scavenge free radicals and reduce oxidative stress. It may also have potential therapeutic applications in the treatment of various diseases and conditions, although further research is needed to fully understand its biological activities and potential uses.

InChI:InChI=1/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 121-33-5 vanillin 
• 123-54-6 acetylacetone 
• 932744-42-8 di-O-acetylbisdemethoxycurcumin 
• 932744-41-7 di-O-acetyldemethoxycurcumin 

Downstream Products

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 7400-08-0 p-Coumaric Acid 
• 149579-07-7 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione 
• 869789-09-3 (1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione 
• 824951-60-2 di-O-methyldemethoxycurcumin 
• 932744-42-8 di-O-acetylbisdemethoxycurcumin 
• 932744-41-7 di-O-acetyldemethoxycurcumin 
• 1221590-00-6 C₂₇H₂₂O₆ 
• 1221589-99-6 C₂₇H₂₂O₆ 
• 1221590-01-7 C₃₄H₂₆O₇ 
• 1221589-95-2 di-O-(3,3-dimethylallyl)demethoxycurcumin 
• 1221589-96-3 mono-4''-O-(2-hydroxyethyl)demethoxycurcumin 
• 1246537-00-7 mono-O'-acetyldemethoxycurcumin 
• 888024-28-0 mono-O''-acetyldemethoxycurcumin 

Relevant articles and documents

Synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment

A novel series of succinyl derivatives of three curcuminoids were synthesized as potential prodrugs. Symmetrical (curcumin and bisdesmethoxycurcumin) and unsymmetrical (desmethoxycurcumin) curcuminoids were prepared through aldol condensation of 2,4-pentanedione with different benzaldehydes. Esterification of these compounds with a methyl or ethyl ester of succinyl chloride gave the corresponding succinate prodrugs in excellent yields. Anticolon cancer activity of the compounds was evaluated using Caco-2 cells. The succinate prodrugs had IC50 values in the 1.8-9.6 μM range, compared to IC50 values of 3.3-4.9 μM for the parent compounds. Curcumin diethyl disuccinate exhibited the highest potency and was chosen for stability studies. Hydrolysis of this compound in phosphate buffer at pH 7.4 and in human plasma followed pseudo first-order kinetics. In phosphate buffer, the κobs and t1/2 for hydrolysis indicated that the compound was much more stable than curcumin. In human plasma, this compound was able to release curcumin, therefore our results suggest that succinate prodrugs of curcuminoids are stable in phosphate buffer, release the parent curcumin derivatives readily in human plasma, and show anti-colon cancer activity.

Facile preparation of new unsymmetrical curcumin derivatives by solid-phase synthesis strategy

Seventeen unsymmetrical curcumin derivatives were synthesized in good yield and purity by a facile solid phase synthesis strategy.

Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria

Bioassay-directed fractionation of an EtOH extract of Curcuma zedoaria led to isolation of an active curcuminoid, which was identified as demethoxycurcumin (2) by comparison of its 1H and 13C NMR spectra with literature data and by direct comparison with synthetic material. Curcumin (1) and bisdemethoxycurcumin (3) were also obtained. Curcuminoids (1-3) were synthesized and demonstrated to be cytotoxic against human ovarian cancer OVCAR-3 cells. The observed CD50 values of 1, 2, and 3 were 4.4, 3.8, and 3.1 μg/mL, respectively. Three additional novel compounds, 3,7- dimethylindan-5-carboxylic acid (4), curcolonol (5), and guaidiol (6), were also isolated from the EtOH extract. The structures and relative stereochemistry of 4-6 were determined by spectroscopic methods and X-ray crystallographic analysis.