2530-99-6

Basic information

• Product Name: 1-Allyl-3,7-dimethylxanthine
• Synonyms: 1-Allyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione;1-Allyl-3,7-dimethylxanthine;1-Allyltheobromine;3,7-Dihydro-3,7-dimethyl-1-(2-propenyl)-1H-purine-2,6-dione
• CAS NO: 2530-99-6
• Molecular Formula: C₁₀H₁₂N₄O₂
• Molecular Weight: 220.26
• Mol File: 2530-99-6.mol

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 361.16°C (rough estimate)
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.2387 (rough estimate)
• Vapor Pressure: 1.17E-07mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• PKA: 0.47±0.70(Predicted)
• CAS DataBase Reference: 1-Allyl-3,7-dimethylxanthine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Allyl-3,7-dimethylxanthine(2530-99-6)
• EPA Substance Registry System: 1-Allyl-3,7-dimethylxanthine(2530-99-6)

Safety Data

• Hazardous Substances Data: 2530-99-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Allyl-3,7-dimethylxanthine is used as a central nervous system stimulant for increasing alertness and improving cognitive function, similar to the effects of caffeine.
Used in Cardiovascular Applications:
As a vasodilator, 1-Allyl-3,7-dimethylxanthine is used in the treatment of cardiovascular disorders to improve blood flow and reduce strain on the heart.
Used in Respiratory Treatment:
1-Allyl-3,7-dimethylxanthine is used in the treatment of respiratory diseases, potentially aiding in the management of conditions such as asthma or chronic obstructive pulmonary disease (COPD) by relaxing the airways and improving breathing.
Used in Anti-inflammatory Applications:
Due to its potential anti-inflammatory properties, 1-Allyl-3,7-dimethylxanthine may be used in the development of treatments for inflammatory conditions, helping to reduce inflammation and alleviate symptoms.
Used in Oncology Research:
1-Allyl-3,7-dimethylxanthine is studied for its potential anti-cancer properties, with ongoing research exploring its use in the development of cancer therapies and its effects on various types of cancer cells.

InChI:InChI=1/C10H12N4O2/c1-4-5-14-9(15)7-8(11-6-12(7)2)13(3)10(14)16/h4,6H,1,5H2,2-3H3

Upstream product

• 83-67-0 theobromine / 
• 106-95-6 allyl bromide 
• 6493-05-6 pentoxyphylline 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 
• 97202-78-3 2-chloro-6-ethoxy-7-methylpurine 
• 97184-74-2 2,6-dimethoxy-7-methyl-purine 
• 2273-93-0 2,6-dichloro-7-methylpurine 
• 97184-80-0 2-methoxy-7-methyl-6-(2-propenyloxy)-7H-purine 
• 556-56-9 allyl iodid 

Downstream Products

• 900890-59-7 C₁₇H₁₅Cl₂N₅O₃ 
• 900277-96-5 C₁₉H₂₁N₅O₅ 
• 900901-17-9 C₁₇H₁₇N₅O₃ 
• 906262-02-0 C₁₉H₂₂N₆O₃ 
• 900289-13-6 C₁₇H₁₆ClN₅O₃ 
• 900896-06-2 C₁₇H₁₆BrN₅O₃ 
• 63906-63-8 3,7-Dimethyl-1-propylxanthine 
• 50-39-5 Vascopil 
• 1161823-24-0 1-allyl-3,7-dimethyl-8-(p-tolyl)-xanthine 

Relevant articles and documents

Reaction of 1-Allyl(methallyl)theobromine with Halogens

The reactions of bromine and iodine with 1-allyltheobromine and 1-methallyltheobromine were studied. Depending on the nature of the halogen and the initial theobromine, the reaction can lead to the formation of the adducts at the double bond, oxazolopurines or complex compounds.

Design, synthesis, antiviral, and cytostatic evaluation of novel isoxazolidine analogs of homonucleotides

Moderate diastereoselectivities (d.e. 2-62%) of isoxazolidine homonucleotides were observed for cycloadditions between N-methyl-C- (diethoxyphosphoryl)nitrone and N-allyl nucleobases, with trans-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil-containing cycloadducts. The cis- and trans-isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33-100 μM.

Synthesis of PS-supported NHC-Pd catalyst derived from theobromine and its applications in Suzuki-Miyaura reaction

The synthesis of the PS-supported bis-NHC-palladium catalyst simply prepared from theobromine in four steps was reported. The air-stable PS-supported bis-NHC-Pd catalyst can be used as a good catalyst in running Suzuki-Miyaura cross-coupling reaction.

Photochemistry synthesis. Part 1: Syntheses of xanthine derivatives by photolysis of 1-(5′-oxohexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione (pentoxifylline): an ambident chromophore

We investigated the use of photochemistry to make novel derivatives of pentoxifylline. Under conditions that favour singlet excited states, we obtained 1-allyl-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione, (R*,R*)-(±)-1-{[2-hydroxy-2-methylcyclobutyl]methyl}-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione and 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione. Naphthalene or molecular oxygen increases the yields and triplet sensitisers (acetophenone, benzophenone and acetone) decrease the yields. Efficient intramolecular triplet energy transfer from the carbonyl to the xanthine moiety allows the carbonyl moiety to react from a singlet excited state only. In solvents with an α-hydroxyalkyl hydrogen under conditions that favour triplet excited states, we obtained 8-substituted pentoxifylline derivatives: 8-(1-hydroxy-1-methylethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione in isopropanol, 8-(1-hydroxymethyl)-3,7-dimethyl-1-(5-oxo-hexyl)-3,7-dihydro-1H-purine-2,6-dione in methanol and 8-(1-hydroxyethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione in ethanol. The xanthine moiety reacts from a triplet state via a radical mechanism and yields are considerably improved by the addition of catalytic amounts of di-tert-butyl peroxide.

Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- Positions using biocatalysts

A bacterial consortium consisting of strains belonging to the genus Klebsiella and Rhodococcus quantitatively converts 1-, 3- and 7-substituted xanthines to their respective 8-oxo compounds.

Olefin substituted long chain compounds

There is disclosed an olefin-substituted compound having the formula:R--(core moiety),wherein R is a straignt chain hydrocarbon having at least one double bond and a carbon chain length of from about 6 to about 18 carbon atoms, wherein multiple double bonds are separated from each other by at least three carbon atoms, wherein the closest double bond to the core moiety is at least five carbon atoms from the core moiety, and wherein the hydrocarbon chain may be substituted by a hydroxyl, halo, keto or dimethylanimo group and/or interrupted by an oxygen atom and salts thereof and pharmaceutical compositions thereof.

Analogue of Coffeine and Theophylline: Effect of Structural Alterations on Affinity at Adenosine Receptors

A variety of analogues of caffeine and theophylline in which the 1-, 3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in few cases with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and s

2,6-Dialkoxy-7-methylpurines

The preparation of unsymmetrical 2,6-dialkoxy-7-methylpurines (2), and 2-alkoxy-1,7-dialkyl-6-oxo-1,6-dihydropurines (5) is described.In contrast to 1 and 2, a facile thermal lactim-lactam rearrangement from hypoxanthines 5 and 7 into xanthines 6 was observed. - Keywords: Nucleophilic heteroaromatic substitution; thermal lactim-lactam rearrangement; Sigmatropic shifts; Dialkoxy-7H-purines; Dialkyl-1H(or 3H),7H-hypoxanthines; Trialkyl-7H-xanthines