22608-11-3

Basic information

• Product Name: DEMETHOXYCURCUMIN
• Synonyms: Feruloyl-P-hydroxycinnnamoylmethane;Demethoxycurcumin;1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-;MonodeMethoxycurcuMin;(1E,6E)-1-(4-Hydroxyphenyl)-7-(4-hydroxy-3-Methoxyphenyl)-1,6-heptadiene-3,5-d;(E,E)-1-(4-Hydroxy-3-Methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;1-(4-Hydroxy-3-Methoxyphenyl)-7-(p-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• CAS NO: 22608-11-3
• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.35
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 22608-11-3.mol

Chemical Properties

• Melting Point: 166～170℃
• Boiling Point: 571.4 °C at 760 mmHg
• Flash Point: 205.5 °C
• Appearance: orange/
• Density: 1.282 g/cm³
• Vapor Pressure: 1.17E-13mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥10mg/mL
• PKA: 8.31±0.46(Predicted)
• CAS DataBase Reference: DEMETHOXYCURCUMIN(CAS DataBase Reference)
• NIST Chemistry Reference: DEMETHOXYCURCUMIN(22608-11-3)
• EPA Substance Registry System: DEMETHOXYCURCUMIN(22608-11-3)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 22608-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Demethoxycurcumin is used as an anti-inflammatory and anti-proliferative agent for its ability to regulate responses through a ROS-independent mechanism. It down-regulates the transcriptional coactivator p300, suppressing the Wnt/β-catenin pathway, and inhibits lipopolysaccharide induction of iNOS.
Used in Cancer Research:
In cancer research, DMC is used as a potential therapeutic agent for its ability to suppress the proliferation of cancer cells at concentrations of 50-100 μM. Its down-regulation of the transcriptional coactivator p300 and suppression of the Wnt/β-catenin pathway make it a promising candidate for further investigation into its potential applications in cancer treatment.
Used in Drug Development:
Demethoxycurcumin can be used in the development of novel drug delivery systems to enhance its applications and efficacy against various diseases, including cancer. Researchers can explore the use of organic and metallic nanoparticles as carriers for DMC delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Used in Analytical Chemistry:
As a primary reference substance with assigned absolute purity, DMC can be used in analytical chemistry for the development and validation of analytical methods, quality control, and standardization of procedures involving the analysis of curcumin and its derivatives.

Biochem/physiol Actions

Demethoxycurcumin (DMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. DMC inhibits LPS-induced nitric oxide (NO) production, and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. DMC also inhibits NF-kB dependent iNOS, TNFα and IL-1β expression in LPS-treated rat microglial cells. DMC suppresses expression of MMPs and ICAM-1 in MDA-MB-231 human breast cancer cells by inhibition of NF-kB.

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

• 123-54-6 acetylacetone 
• 121-33-5 vanillin 
• 123-08-0 4-hydroxy-benzaldehyde 
• 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 
• 932744-42-8 di-O-acetylbisdemethoxycurcumin 
• 932744-41-7 di-O-acetyldemethoxycurcumin 
• 908094-05-3 5-hydroxy-7-(4-hydroxyl-3-methoxyphenyl)-1-(4-hydroxylphenyl)-3-heptanone 
• 138870-92-5 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one 
• 149579-07-7 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione 
• 1246537-27-8 C₂₂H₂₁NO₄ 
• 1246537-21-2 C₂₂H₂₁NO₄ 

Relevant articles and documents

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.

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.

METHOD TO PREPARE PURE CURCUMIN

This invention describes a preparation of at least 99% by weight pure curcumin from less pure grades of curcumin utilizing phenol protecting groups to favor a selective recrystallization of curcumin in the presence of demethoxycurcumin and bis-demethoxycurcumin and other curcuminoids of minor composition.

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.

Synthesis and biological evaluation of polyhydroxycurcuminoids

A series of curcumin analogs (1-3, 5a-5t) was synthesized through the condensation of appropriately protected hydroxybenzaldehydes with acetylacetone, followed by deprotection. The antioxidant activity of these analogs was determined by superoxide free radical nitroblue tetrazolium and DPPH free radical scavenging methods and the polyhydroxycurcuminoids (5l-5s) displayed excellent antioxidant activity. These analogs showed cytotoxicity to lymphocytes and promising tumor-reducing activity on Dalton's lymphoma ascites tumor cells.

Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action

We have previously reported the inhibitory activity of curcumin against human immunodeficiency virus type one (HIV-1) integrase. In the present study, we have synthesized and tested analogs of curcumin to explore the structure-activity relationships and mechanism of action of this family of compounds in more detail. We found that two curcumin analogs, dicaffeoylmethane (6) and rosmarinic acid (9), inhibited both activities of integrase with IC50 values below 10 μM. We have previously demonstrated that lysine 136 may play a role in vital DNA binding. We demonstrated equivalent potencies of two curcumin analogs against both this integrase mutant and wild-type integrase, suggesting that the curcumin-binding site and the substrate-binding site may not overlap. Combining one curcumin analog with the recently described integrase inhibitor NSC 158393 resulted in integrase inhibition which was synergistic, reflective of drug-binding sites which may not overlap. We have also determined that these analogs can inhibit binding of the enzyme to the viral DNA but that this inhibition is independent of divalent metal ion. Furthermore, kinetic studies of these analogs suggest that they bind to the enzyme at a slow rate. These studies can provide mechanistic and structural information which may guide the future design of integrase inhibitors.