19697-86-0

Basic information

• Product Name: curcumin 4,4'-diacetate
• Synonyms: curcumin 4,4'-diacetate;DIACETYLCURCUMIN;BIS-ACETATECURCUMIN
• CAS NO: 19697-86-0
• Molecular Formula: C₂₅H₂₄O₈
• Molecular Weight: 452.45326
• Mol File: 19697-86-0.mol

Chemical Properties

• Boiling Point: 595.4°Cat760mmHg
• Flash Point: 255.3°C
• Appearance: /
• Density: 1.235g/cm³
• CAS DataBase Reference: curcumin 4,4'-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: curcumin 4,4'-diacetate(19697-86-0)
• EPA Substance Registry System: curcumin 4,4'-diacetate(19697-86-0)

Safety Data

• Hazardous Substances Data: 19697-86-0(Hazardous Substances Data)

Upstream product

• 458-37-7 curcumin 
• 108-24-7 acetic anhydride 
• 98885-93-9 curcumin 
• 75-36-5 acetyl chloride 
• 123-54-6 acetylacetone 
• 121-33-5 vanillin 
• 64-19-7 acetic acid 

Downstream Products

• 52199-86-7 1,7-bis(4’-acetoxy-3’-methoxyphenyl)-3,5-heptadione 

Relevant articles and documents

Full structural characterization of homoleptic complexes of diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level Cytotoxicity in Vitro with Minimal Acute Toxicity in Vivo

At the present time, scientists place a great deal of effort worldwide trying to improve the therapeutic potential of metal complexes of curcumin and curcuminoids. Herein, the synthesis of four homoleptic metal complexes with diacetylcurcumin (DAC), using a ligand designed to prevent the interaction of phenolic groups, rendering metal complexes through the β-diketone functionality, is reported. Due to their physiological relevance, we used bivalent magnesium, zinc, copper, and manganese for complexation with DAC. The resulting products were characterized by ultraviolet-visible (UV-Vis), fluorescence spectroscopy, infrared spectroscopy (IR), liquid and solid-state nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), magnetic moment, mass spectrometry (MS), single crystal, and powder X-ray diffraction (SCXRD and PXRD). Crystallization was achieved in dimethylsulfoxide (DMSO) or N,N-dimethylformamide (DMF) as triclinic systems with space group P-1, showing the metal bound to the β-diketone function, while the 1H-NMR confirmed the preference of the enolic form of the ligand. Single crystal data demonstrated a 1:2 metal:ligand ratio. The inhibition of lipid peroxidation was evaluated using the thiobarbituric acid reactive substance assay (TBARS). All four metal complexes (Mg, Zn, Cu, and Mn) exhibited good antioxidant effect (IC50 = 2.03 ± 0.27, 1.58 ± 0.07, 1.58 ± 0.15 and 1.24 ± 0.10 μM respectively) compared with butylated hydroxytoluene (BHT) and α-tocopherol. The cytotoxic activity in human cancer cell lines against colon adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and lung adenocarcinoma (SKLU-1) was found comparable ((DAC)2Mg), or ca. 2-fold higher ((DAC)2Zn) than cisplatin. The acute toxicity assays indicate class 5 toxicity, according to the Organization for Economic Co-operation and Development (OECD) guidelines at doses of 3 g/kg for all complexes. No mortality or changes in the behavior of animals in any of the treated groups was observed. A therapeutic potential can be envisaged from the relevant cytotoxic activity upon human cancer cell lines in vitro and the undetected in vivo acute toxicity of these compounds.

Inhibition of amyloid fibril formation of β-lactoglobulin by natural and synthetic curcuminoids

The aggregation of proteins has been associated with several aspects of daily life, including food processing, blood coagulation and many neurodegenerative infections. However, the actual mechanisms responsible for amyloidosis, the irreversible fibril for

Synthesis and characterization of acetyl curcumin-loaded core/shell liposome nanoparticles via an electrospray process for drug delivery, and theranostic applications

Despite substantial advancements in divergent drug delivery systems (DDS), there is still room for novel and innovative nanoparticle-mediated drug delivery methodologies such as core/shell liposomes to deliver drugs in a kinetically controlled manner into

Efficient esterification of curcumin in bis(trifluoromethylsulfonyl)imide-based ionic liquids

In this paper, the potential application of bis(trifluoromethylsulfonyl)imide based ionic liquids paired with various cations (ammonium, piperidinium, pyridinium and imidazolium) as the recyclable reaction media for the esterification of curcumin has been

Preparation method of tetrahydrocurcumin and intermediate thereof

The invention provides a preparation method of tetrahydrocurcumin and an intermediate thereof, and the preparation method of the intermediate comprises the following steps: step a, in the presence ofalkali, reacting a compound (IV) with an acetylation reagent in a solvent to obtain a compound (III); b, in the presence of a catalyst and a solvent, the compound (III) and hydrogen or a hydrogen donor are subjected to a reduction reaction to obtain a compound (II), namely the tetrahydrocurcumin intermediate; and the tetrahydrocurcumin preparation method comprises the step that acetyl is removed from the compound (II) in the solvent in the presence of alkali to obtain a compound (I), namely tetrahydrocurcumin. The selectivity of the diacetyl curcumin reduction reaction is far superior to thatof direct reduction of curcumin, and the yield is high; the method is simple and convenient in purification and high in product content, and hardly contains curcumin, hexahydrocurcumin and octahydrocurcumin; the method disclosed by the invention is simple and feasible to operate, stable and durable in process, easy to control, easy to amplify and convenient in post-reaction treatment, and can be economically and conveniently used for industrial production.

Synthesis, antifungal evaluation and molecular docking studies of some tetrazole derivatives

A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diamin-obenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.

Use of curcumin derivative

The invention provides the use of a curcumin derivative. The use of the curcumin derivative shown in a formula I (please see the specification for the formula), or salts of the curcumin derivative inthe preparation of drugs of anti-inflammatory diseases and/or a COX inhibitor is particularly provided. The curcumin derivative has good COX inhibitory activity and anti-inflammatory activity and canbe used for preparing the COX inhibitor and anti-inflammatory drugs. Compound 6 and compound 7 have the best effects on COX-2 inhibitory activity and anti-inflammatory activity and can be used for preparing a COX-2 inhibitor and the anti-inflammatory drugs.

Method for restraining proliferation of tumor cells through cooperation of 4,4-dimethyl curcumin with ultrasonic

The invention relates to a method for restraining proliferation of tumor cells through cooperation of 4,4-dimethyl curcumin with ultrasonic, and belongs to the technical field of medicine. The proliferation of the tumor cells is restrained through coopera

Four mammalian keratinous analogue and its preparation and use

The invention belongs to the technical field of medical technology and relates to a series of tetrahydrocurcumin analogues, a preparation and an application thereof. The tetrahydrocurcumin analogue is characterized by having a structure represented as for

Synthesis of curcuminoids and evaluation of their cytotoxic and antioxidant properties

Curcumin (1) and ten derivatives (2-11) were synthesized and evaluated as cytotoxic and antioxidant agents. The results of primary screening by Sulforhodamine B assay against five human cancer cell lines (U-251 MG, glioblastoma; PC-3, human prostatic; HCT-15, human colorectal; K562, human chronic myelogenous leukemia; and SKLU-1, non-small cell lung cancer) allowed us to calculate the half maximal inhibitory concentration (IC50) values for the more active compounds against HCT-15 and K562 cell lines. Compounds 2 and 10 were the most active against both cell lines and were more active than curcumin itself. Thiobarbituric acid reactive substances (TBARS) assay showed that 7 has potent activity; even stronger than curcumin, α-tocopherol, and quercetin.