54135-60-3

Basic information

• Product Name: 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE)
• Synonyms: M50054;2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE);2,2-METHYLENEBIS-(1,3-CYCLOHEXANEDIONE);2,2'-METHYLENE BIS CYCLOHEXANE-1,3-DIONE;2-[(2,6-dioxocyclohexyl)methyl]cyclohexane-1,3-dione
• CAS NO: 54135-60-3
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.26
• EINECS: 258-989-1
• Product Categories: Inhibitor
• Mol File: 54135-60-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 461.2 °C at 760 mmHg
• Flash Point: 199 °C
• Appearance: /
• Density: 1.227 g/cm³
• Storage Temp.: +2C to +8C
• Solubility: Soluble in DMSO or ethanol
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE)(54135-60-3)
• EPA Substance Registry System: 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE)(54135-60-3)

Safety Data

• Hazardous Substances Data: 54135-60-3(Hazardous Substances Data)

Usage

Uses

A cell-permeable inhibitor of apoptosis induction. Inhibits caspase-3 activation but does not directly inhibit caspase-3 even at 1 mg/ml.

Biological Activity

m50054, 2,2'-methylenebis (1,3-cyclohexanedione), is a novel inhibitor of apoptosis. [1]in human fas-expressing wc8 cells, m50054 inhibited apoptosis by soluble human fas ligand in vitro cell death assay. m50054 inhibited the apoptotic u937 cell death which is a human monocytic leukemic cell line, induced by anticancer agents such as etoposide. m50054 inhibited apoptotic characters such as dna phosphatidylserine and fragmentation exposure in these cells. these anti-apoptotic effects were dependent on inhibition of caspase-3 activation. additionally, m50054 significantly inhibited anti-fas-antibody-induced elevation of plasma aspartate aminotransferase and alanine aminotransferase. alopecia (hair loss) symptoms were also significantly improved with topical treatment with m50054. m50054 inhibits apoptosis induced by a variety of stimuli via inhibition of caspase-3 activation, and may thus be effective for hepatitis and chemotherapy-induced alopecia. [1]

references

tsuda t, ohmori y, muramatsu h et al. inhibitory effect of m50054, a novel inhibitor of apoptosis, on anti-fas-antibody-induced hepatitis and chemotherapy-induced alopecia.eur j pharmacol. 2001 dec 14;433(1):37-45.

Upstream product

• 5146-68-9 N-(Hydroxymethyl)succinimide 
• 504-02-9 1,3-cylohexanedione 
• 30038-67-6 1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene 
• 7732-18-5 water 
• 50-00-0 formaldehyd 

Downstream Products

• 505-52-2 brassylic acid 
• 61137-12-0 3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione 
• 1040735-65-6 ethyl 2-(2-ethoxycarbonylethyl)-3-oxocyclohexenebutyrate 
• 817624-74-1 10-(2-methoxyphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione 
• 55998-74-8 3-(methylamino)-2-cyclohexen-1-one 
• 15581-39-2 Bis-<2-benzolsulfonylhydrazino-6-oxo-cyclohexen-(1)-yl>-methan 
• 21081-45-8 2.2'-Methylen-bis-<1-phenylhydrazino-cyclohexen-(1)-on-(3)> 
• 128229-77-6 N-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 

Relevant articles and documents

The crystal structure and conformational studies of acridinedione derivatives

Two crystal structures of acridinediones namely, TMHAD and MPHAD were studied by X-ray crystallographic method in view of their occurrence in numerous commercial products including pharmaceuticals, fragrances and dyes. Crystal data of TMHAD are: C17H23NO2, orthorhombic, Fdd2, with cell parameters a = 40.417(6) A, b = 5.744(1) A, c = 12.979(2) A, V = 3013.1(7) A3, Z = 8, Dcal = 1.205 Mg/m3, μ = 0.078 mm-1. Crystal data of MPHAD are: C20H18NO3; monoclinic, P21/c with cell parameters a = 10.182(9) A, b = 17.105(14) A, c = 10.895(9) A, β = 117.857(1)°, V = 1678(2) A3, Z = 4, Dcal = 1.268 Mg/m3, μ = 0.085 mm-1. Both data were collected using λ (MoKα) = 0.71073 A. The central ring in the acridinedione moieties tends to be planar while the outer two rings adopt sofa conformations. Intermolecular interactions of C-H...O type of hydrogen bond help the molecules to stabilize into the crystal packing. Interestingly, a week forces of C-H...π interactions also helps the molecules for stabilization. Graphical Abstract: Two crystal structures of acridinediones namely, TMHAD and MPHAD have been synthesized and its structural chemistry has been proved by crystallographic study.

Thermal and microwave assisted synthesis of N-aroylamino acridinediones

A series of N-aroylamino acridinediones (3a-3d and 6a-6e) have been synthesized from tetraketones (1 and 4) and benzoic hydrazides (2a-2d and 5a-5e) under thermal and microwave irradiation conditions with solid supports.

A New Class of Laser Dyes from Acridinedione Derivatives

Synthesis of 10-aryl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione as a new class of laser dyes is reported.These dyes lase around 475-495 nm and are compared to the standard dye coumarin 102.