893-00-5

Basic information

• Product Name: 2,6-Di(2-furylmethylidene)cyclohexan-1-one
• Synonyms: 2,6-Di(2-furylmethylidene)cyclohexan-1-one
• CAS NO: 893-00-5
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 254.28
• Mol File: 893-00-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 422.9°C at 760 mmHg
• Flash Point: 204.5°C
• Appearance: /
• Density: 1.245g/cm³
• Vapor Pressure: 2.33E-07mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 2,6-Di(2-furylmethylidene)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Di(2-furylmethylidene)cyclohexan-1-one(893-00-5)
• EPA Substance Registry System: 2,6-Di(2-furylmethylidene)cyclohexan-1-one(893-00-5)

Safety Data

• Hazardous Substances Data: 893-00-5(Hazardous Substances Data)

Usage

Chemical Family

Furan derivatives

Physical State

Yellowish liquid

Odor

Strong, sweet

Usage

Flavoring agent in the food industry

Synthesis

Used in the production of pharmaceuticals and agrochemicals

Medical Applications

Potential anti-inflammatory and anti-cancer properties

Safety

Potentially hazardous if not properly controlled and handled

InChI:InChI=1/C16H14O3/c17-16-12(10-14-6-2-8-18-14)4-1-5-13(16)11-15-7-3-9-19-15/h2-3,6-11H,1,4-5H2

Upstream product

• 15022-16-9 2-(furan-2-yl)acetaldehyde 
• 108-94-1 cyclohexanone 
• 98-01-1 furfural 

Relevant articles and documents

Synthesis of furan derivative as LED light photoinitiator: One-pot, low usage, photobleaching for light color 3D printing

A type II photoinitiator, containing furan structure, 2,6-bis(furan-2-ylmethylidene) cyclohexan-1-one (BFC) was synthesized via one step reaction between furan and cyclohexanone. This photoinitiator has large molar extinction coefficient and long wavelength absorption attributing to its large conjugation structure. Photopolymerization kinetics reveals that photoinitiator BFC at low concentration exhibits the high polymerization rate and conversion. UV-vis absorption and fluorescence spectrum demonstrate that BFC has a big red shift in the polyethylene glycoldiacrylate (PEGDA) solution and the light absorption region could be extended to 500 nm because of exciplex formed by BFC and PEGDA. Moreover, PEGDA is the excellent hydrogen donor to photoinitiator BFC compared with traditional coinitator amine. This BFC/PEGDA photoinitiator system has an outstanding photobleaching performance, which has potential to be used in the light-color materials with visible light photopolymerization, such as 3D photopolymerization printing material with long wavelength LED lamp.

Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Inflammation is a pathophysiological condition which progresses through the prostaglandin (PG) and leukotriene (LT) pathways channelized by the enzymes COX/mPGES1 and 5-LOX respectively. Diarylidenecyclohexanone (DAC) derivatives (Ia-j, IIa-c, IIIa and IVa) were synthesized, characterized and screened for their in vitro anti-inflammatory activity via inhibition of 5-LOX and COX-2/mPGES1 enzymes. Compound Ic inhibited PGE2 production exhibiting an IC50 of 6.7 ± 0.19 μM, comparable to the standard inhibitor, licofelone (IC50 of 5.4 ± 0.02 μM). Compounds Ie and Ig showed maximum in vitro inhibitory activity against 5-LOX, exhibiting an IC50 of 1.4 ± 0.1 μM and 1.5 ± 0.13 μM, respectively, and these are comparable to that of the standard drug, zileuton (IC50 = 1.2 ± 0.11 μM). Ie and Ig do not possess radical scavenging properties and may not be disrupting the redox cycle of the enzyme. Hence they may be inhibiting the enzyme by a competitive mode. One of the compounds in the DAC series (IIc) containing a heterocyclic thienyl ring inhibited all the three enzymes. It inhibited 5-LOX and COX-2/mPGES1 with an IC50 of 1.8 ± 0.12 μM and 7.5 ± 0.4 μM respectively. An RT-PCR based mRNA expression study highlighted that Ic predominantly inhibited the expression of COX-2 rather than mPGES1. No toxicity towards the HeLa cell line indicated that the DACs could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs as anti-inflammatory agents.

Preparation method for synthesizing photosensitive compound through Claisen-Schmidt reaction

The invention provides a preparation method for synthesizing a photosensitive compound through a Claisen-Schmidt reaction. An aldehyde free of alpha-H and a ketone containing alpha-H are selected to be synthesized to obtain the product alpha, beta-unsaturated aldehyde ketone. The preparation method is simple in condition and mild in reaction. The prepared photosensitive compound serving as a hydrogen abstraction type photoinitiator is long in wave length and small in consumption, and has a good initiation effect on monomer PEFDA without adding initiation auxiliaries. Under an ultraviolet lamp,the absorption wavelength is subjected to red shift from 450 to 500 and finally subjected to blue shift to 400 or below. The photosensitive compound has an AIE effect.