10226-54-7

Basic information

• Product Name: LOMIFYLLINE
• Synonyms: LOMIFYLLINE;3，7-Dihydro-1，3-dimethyl-7-(5-oxohexyl)-1H-pmfine-2，6-dione;Cervilane;Lomifilline;3,7-Dihydro-1,3-dimethyl-7-(5-oxohexyl)-1H-purine-2,6-dione;1,3-DiMethyl-7-(5-oxohexyl)xanthine;7-(5-Oxohexyl)-1,3-diMethylxanthine;7-(5-Oxohexyl)theophylline
• CAS NO: 10226-54-7
• Molecular Formula: C₁₃H₁₈N₄O₃
• Molecular Weight: 278.31
• EINECS: 233-547-0
• Mol File: 10226-54-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 525.3°Cat760mmHg
• Flash Point: 271.5°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 3.97E-11mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: LOMIFYLLINE(CAS DataBase Reference)
• NIST Chemistry Reference: LOMIFYLLINE(10226-54-7)
• EPA Substance Registry System: LOMIFYLLINE(10226-54-7)

Safety Data

• Hazardous Substances Data: 10226-54-7(Hazardous Substances Data)

Usage

Originator

Lomifylline,Yick-Vic Chemicals and

Uses

Lomifylline is a methylxanthine analogue which induces Ca2+-release from intracellular stores via the ryanodine receptor.

Manufacturing Process

A mixture of 560 g of potassium carbonate, 700 ml of ethanol (96%), 404 g of 1,3-dibromopropane and 260 g of ethyl acetoacetate was heated with stirring to go 60°C. After the reaction had subsided, the reaction mixture was refluxed for 5 hours. Then the bulk of the alcohol was distilled off under ordinary pressure and the residue was mixed with 1.5 L of water. The resulting oily layer was separated, and the aqueous phase was extracted with benzene and the benzene layer was combined with the oil. After drying with sodium sulfate the benzene was distilled off and the residue was fractionally distilled 250 g (73% of theory) of 2-methyl-3-carbethoxy-5,6-dihydropyrane of boiling point 105°-108°C were obtained.140 ml of 63% hydrobromic acid were slowly added at room temperature to 128 g of 2-methyl-3-carbethoxy-5,6-dihydropyrane, and much carbon dioxidewas evolved. After standing for 1 to 2 days at room temperature the mixture was diluted with an equal volume of iced water; the layer of dark colored oil formed was separated, the aqueous phase was extracted with chloroform, and the extract was combined with the oil and washed with a saturated solution of sodium bicarbonate. The solution was dried with sodium sulfate, the chloroform was distilled off under normal pressure, and the residue was fractionally distilled in vacuo. 109 g (81% of theory) of 1-bromohexanone-5 of boiling point 94°-98°C/12 mm Hg were obtained.A solution of 10.0 g of 1-bromohexanone-5 in 100 ml of ethanol was gradually mixed at the boil with vigorous stirring with 11.3 g of the sodium salt of theophylline in 100 ml of water. After 3 hours refluxing the alcohol was distilled off, and the residual aqueous phase was cooled and made alkaline and extracted with chloroform. The chloroform solution was evaporated and the residue re-crystallized from a little isopropanol to yield 7-(5-oxohexyl) theophylline. MP: 75°-76°C; a yield of about 80% (calculated on the reacted theophylline).

Therapeutic Function

Vasodilator

InChI:InChI=1/C13H18N4O3/c1-9(18)6-4-5-7-17-8-14-11-10(17)12(19)16(3)13(20)15(11)2/h8H,4-7H2,1-3H3

Upstream product

• 58-55-9 theophylline 
• 87307-20-8 trimethyl 5-bromoorthopentanoate 
• 10297-06-0 1-chloro-5-hexyne 
• 71280-22-3 toluene-4-sulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-butyl ester 
• 109-49-9 5-Hexen-2-one 
• 5745-75-5 4-(2-methyl-[1,3]-dioxolan-2-yl)butan-1-ol 
• 20449-21-2 2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane 

Downstream Products

• 19493-09-5 Methylenetriphenylphosphorane 

Relevant articles and documents

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Potentiation of cADPR-induced Ca2+-release by methylxanthine analogues

Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7- hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR- induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.