24939-16-0

Basic information

• Product Name: BIS(4-HYDROXYCINNAMOYL)METHANE
• Synonyms: BIS-DESMETHOXYCURCUMIN;BIS(4-HYDROXYCINNAMOYL)METHANE;DEMETHOXYCURCUMIN, BIS-;CURCUMIN 3;(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione;BIS-(PARA-HYDROXYCINNAMOYL)METHANE;CURCUMINIII;1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• CAS NO: 24939-16-0
• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.33
• EINECS: 1592732-453-0
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 24939-16-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 91-93℃
• Boiling Point: 551.3 °C at 760 mmHg
• Flash Point: 301.3 °C
• Appearance: /
• Density: 1.285
• Vapor Pressure: 9.17E-13mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥20mg/mL
• PKA: 8.67±0.46(Predicted)
• CAS DataBase Reference: BIS(4-HYDROXYCINNAMOYL)METHANE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-HYDROXYCINNAMOYL)METHANE(24939-16-0)
• EPA Substance Registry System: BIS(4-HYDROXYCINNAMOYL)METHANE(24939-16-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 24939-16-0(Hazardous Substances Data)

Usage

General Description

Bis(4-hydroxycinnamoyl)methane is a chemical compound derived from the hydroxycinnamic acid class of compounds, which are naturally occurring in a wide variety of plants. It displays a number of potentially beneficial biological activities, including anti-cancer, anti-inflammatory, and antioxidant effects. Its structure, as the name suggests, consists of a methane molecule bonded to two 4-hydroxycinnamoyl groups. It is a moderately polar, hydrophobic compound that is usually prepared through condensation reactions. Studies suggest that it may have potential applications in medicine and pharmacology due to its bioactive properties.

InChI:InChI=1/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 123-54-6 acetylacetone 
• 932744-42-8 di-O-acetylbisdemethoxycurcumin 
• 932744-41-7 di-O-acetyldemethoxycurcumin 
• 121-33-5 vanillin 
• 67-64-1 acetone 

Downstream Products

• 932744-42-8 di-O-acetylbisdemethoxycurcumin 
• 932744-41-7 di-O-acetyldemethoxycurcumin 
• 1246537-05-2 3,5-bis(4-hydroxystyryl)isoxazole 
• 888024-26-8 mono-O-acetylbisdemethoxycurcumin 
• 41137-85-3 (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone 
• 113482-94-3 1,7-bis(4-hydroxyphenyl)heptane-3,5-dione 

Relevant articles and documents

Preparation method 1,7 - di (4 -hydroxy) heptyl -3-5 - glycol ester

The invention discloses a preparing method of 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester. The method includes the following steps of firstly, conducting a -C=C- reduction reaction with bisdemethoxycurcumin as the raw material to obtain a product 3; secondly, conducting a reduction reaction of carbonyl on the premise of protecting hydroxyl on a benzene ring to obtain a product 5; secondly,conducting an esterification reaction on the product 5 to obtain a product 6, and conducting a protecting group removing reaction on the product 6 to obtain the final product, namely 1,7-bis(4-benzenehydroxyl)heptyl-3,5-glycol ester. By means of the method, through the reduction reaction, the reaction of protecting hydroxyl on the benzene ring, the reaction of reducing carbonyl, the esterification reaction and the protecting group removing reaction, 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester can be obtained; the reaction process is simple, operation is simple, applied raw materials are low in cost, yield is high, and the method is suitable for industrially producing 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester on a large scale.

Method for artificially synthesizing curcumin and derivatives thereof

The invention provides a method for artificially synthesizing curcumin and derivatives thereof. The method comprises the following steps: reacting acetylacetone with boron oxide under a weakly acidiccondition to generate a complex, protecting methylene groups between two ketocarbonyl groups, adding a catalyst, reacting the complex with vanillin (benzaldehyde derivative) to obtain a curcumin derivative intermediate (I), and hydrolyzing the intermediate to obtain the curcumin derivative. The selectivity of the reaction is far higher than that of a preparation reaction in an alkaline system, andis macroscopically and specifically embodied in the yield of curcumin and derivatives thereof: in the existing two-pot reaction, the yield of curcumin in the whole process is about 60%; the yield ofthe preparation method can reach 80-90%. Therefore, the method provided by the invention reduces the waste of raw materials and the generation of byproducts; and complete hydrolysis can be realized only at normal temperature, insoluble substances included in the product are almost zero, and the obtained product is pure.

Synthesis, spectral characterization and thermal analysis of rubrocurcumin and its analogues

Rubrocurcumin and its analogues were synthesized and characterized by UV, IR, NMR and FT-MS spectral data. Thermal analysis of compounds has been carried out using TG-DTG techniques using non-isothermal heating conditions. Flynn–Wall–Ozawa and Kissinger–Akahira–Sunose isoconversional methods were used to determine the apparent activation energies (Ea) for the thermal decomposition rubrocurcumin and its analogues. The Ea values obtained using these methods were used as reference to determine the most suitable kinetic model using Coats–Redfern method. A possible mechanism is suggested to explain the thermal decomposition process. From the TG-DTG data, kinetic parameters have been calculated and were used to evaluate the thermal stability of compounds and the substituent effect on its thermal stability.