Malonaldehyde

Base Information

• Chemical Name: Malonaldehyde
• CAS No.: 542-78-9
• Molecular Formula: C3H4 O2
• Molecular Weight: 72.0636
• Hs Code.: 2912190090
• ICSC Number: 1632
• UNII: 4Y8F71G49Q
• DSSTox Substance ID: DTXSID90202556
• Nikkaji Number: J1.601B
• Wikipedia: Malondialdehyde
• Wikidata: Q418661
• NCI Thesaurus Code: C94711
• RXCUI: 1657018
• Metabolomics Workbench ID: 38821
• ChEMBL ID: CHEMBL446036
• Mol file: 542-78-9.mol

Synonyms:Malonaldehyde;Malondialdehyde;Malondialdehyde, Sodium;Malonylaldehyde;Malonyldialdehyde;Propanedial;Sodium Malondialdehyde

Chemical Property of Malonaldehyde

Chemical Property:

• Vapor Pressure: 26mmHg at 25°C
• Melting Point: 72-74°
• Refractive Index: 1.366
• Boiling Point: 108.3°Cat760mmHg
• PKA: 5(at 25℃)
• Flash Point: 28.9°C
• PSA: 34.14000
• Density: 0.991g/cm³
• LogP: -0.22570
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 72.021129366
• Heavy Atom Count: 5
• Complexity: 34.2

Purity/Quality:

99% ^*data from raw suppliers

MALONALDEHYDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C(C=O)C=O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly.
• General Description: Propanedial (malonaldehyde) is a mutagenic and carcinogenic compound derived from lipid peroxidation and prostaglandin biosynthesis, known for its reactivity with nucleic acids, such as guanosine, leading to the formation of modified nucleosides like pyrimido[1,2-a]purin-10(3H)-one. Its reaction with nucleic acids under acidic conditions, facilitated by precursors like 1,1,3,3-tetraethoxypropane, results in thermally decomposable diastereomers that yield mutagenic adducts efficiently.

Technology Process of Malonaldehyde

There total 44 articles about Malonaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1,3-bis(trimethylsiloxy)propane (17887-80-8) → Malondialdehyde (542-78-9)

Guidance literature:

With chromium(VI) oxide; HZSM-5 zeolite; for 0.025h; microwave irradiation;

DOI:10.1080/10426500490463853

Reference yield: 41.0%

PGH2 methyl ester (63942-75-6) → Malondialdehyde (542-78-9) + (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester (79171-56-5)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; In dichloromethane; at 19 ℃; for 4h;

DOI:10.1021/jo00283a023

Reference yield: 39.0%

(1R*,4R*,5S*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane (113331-81-0,113331-84-3,114738-36-2) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + Malondialdehyde (542-78-9) + (3RS,4SR)-3-hydroxy-4-phenyl-1-cyclopentanone (113331-87-6) + (3SR,4SR)-4,5-epoxy-3-phenyl-1-pentanal (113331-88-7,120708-35-2,120708-36-3) + (1R*,3R*,4S*)-4-phenylcyclopentane-1,3-diol (113331-85-4,114817-51-5,114817-54-8,114817-56-0,120708-38-5) + (2ξ,4RS,6SR)-6-phenyltetrahydropyran-2,4-diol (113331-86-5,113428-36-7,113428-37-8,113428-41-4,119238-85-6)

Guidance literature:

With iron(II) sulfate; In water; acetonitrile; at 0 ℃; for 0.5h; Product distribution; Mechanism;

DOI:10.1039/c39870000722

upstream raw materials:

malondialdehyde bis(diethyl acetal)

3-dimethylaminoacrolein

cyclopropanol

1,3-epiperoxycyclopentane

Downstream raw materials:

4'-(pyrimidin-2-ylsulfamoyl)acetanilide

4-methyl-1,4-dihydro-3,5-pyridinedicarboxaldehyde

1-[2-(3,4-Dihydroxy-phenyl)-ethyl]-4-methyl-1,4-dihydro-pyridine-3,5-dicarbaldehyde

hexan-1-amine

Refernces

Reaction of malonaldehyde with nucleic acid. IV. Formation of pyrimido[1,2-a]purin-10(3H)-one nucleoside by thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine

10.1248/cpb.39.515

The study investigates the reaction of malonaldehyde with nucleic acids, specifically focusing on the formation of pyrimido[1,2-a]purin-10(3H)-one nucleoside (3) through the thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine. Malonaldehyde, a product of lipid peroxidation and prostaglandin biosynthesis, is known for its mutagenic and carcinogenic properties. In this research, guanosine reacts with 1,1,3,3-tetraethoxypropane, which acts as a generator of malonaldehyde, under strongly acidic conditions to form diastereomers 4a and 4b. These diastereomers are then decomposed by heat, yielding the desired pyrimido[1,2-a]purin-10(3H)-one nucleoside (3) in a good yield. The study also proposes a convenient method for the preparation of compound 3, which includes the thermal decomposition process of the diastereomers. The findings suggest that this method is rapid and effective, significantly improving the yield of compound 3 compared to previous methods.