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Xanthobine, also known as 8-Bromo-1,3,7-trimethylxanthine, is a caffeine derivative and a methyl derivative of uric acid. It is an intermediate in the synthesis of 1,3,7-Trimethyluric Acid (T798000) and is commonly detected as a urine marker of caffeine consumption.

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  • 10381-82-5 Structure
  • Basic information

    1. Product Name: xanthobine
    2. Synonyms: xanthobine;8-BROMOCAFFEINE;1,3,7-Trimethyl-8-bromo-7H-purine-2,6(1H,3H)-dione;1,3,7-Trimethyl-8-bromoxanthine;8-Bromo-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;Xanthobin;8-bromo-1,3,7-trimethylpurine-2,6-dione;8-Bromo-1,3,7-trimethylxanthine
    3. CAS NO:10381-82-5
    4. Molecular Formula: C8H9BrN4O2
    5. Molecular Weight: 273.08666
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 10381-82-5.mol
  • Chemical Properties

    1. Melting Point: 208-210°C
    2. Boiling Point: 440.1°Cat760mmHg
    3. Flash Point: 220°C
    4. Appearance: /
    5. Density: 1.87g/cm3
    6. Vapor Pressure: 6.04E-08mmHg at 25°C
    7. Refractive Index: 1.724
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: xanthobine(CAS DataBase Reference)
    11. NIST Chemistry Reference: xanthobine(10381-82-5)
    12. EPA Substance Registry System: xanthobine(10381-82-5)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 10381-82-5(Hazardous Substances Data)

10381-82-5 Usage

Uses

Used in Pharmaceutical Industry:
Xanthobine is used as an intermediate in the synthesis of 1,3,7-Trimethyluric Acid (T798000) for its role in the development of pharmaceutical compounds.
Used in Diagnostic Applications:
Xanthobine is used as a urine marker for caffeine consumption, helping to determine the level of caffeine intake in individuals for various diagnostic purposes.
Used in Research and Development:
Xanthobine serves as a valuable compound in research and development, particularly in the study of caffeine metabolism and its effects on the human body.

Check Digit Verification of cas no

The CAS Registry Mumber 10381-82-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,3,8 and 1 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 10381-82:
(7*1)+(6*0)+(5*3)+(4*8)+(3*1)+(2*8)+(1*2)=75
75 % 10 = 5
So 10381-82-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9BrN4O2/c1-11-4-5(10-7(11)9)12(2)8(15)13(3)6(4)14/h1-3H3

10381-82-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 8-bromo-1,3,7-trimethylpurine-2,6-dione

1.2 Other means of identification

Product number -
Other names Xanthobin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10381-82-5 SDS

10381-82-5Relevant articles and documents

Synthesis of palladium complexes with anionic N,NR- or neutral NH,NR-theophylline-derived NHC ligands

Hahn, F. Ekkehardt,Hervé, Alexandre,Jahnke, Mareike C.,Kampert, Florian

, (2021)

Four C8-halogenated theophyllines (1–4) featuring N7-methyl or N7-allyl and C8-chloro or C8-bromo substituents have been prepared. The halogenotheophyllines react with [Pd(PPh3)4] in an oxidative addition to give complexes of type trans-[Pd(theophyllinato)X(PPh3)2] (trans-[5]–trans-[8]). The protonation of the unsubstituted theophyllinato ring-nitrogen atom to give the pNHC complexes was achieved either by performing the oxidative addition of 1 in the presence of NH4BF4 to give complex trans-[9]BF4 or by N-protonation of the coordinated theophyllinato ligand in trans-[6]–trans-[8] with HBF4·Et2O to give complexes trans-[10]BF4–trans-[12]BF4. The molecular structures of trans-[5], trans-[7], trans-[9]BF4, trans-[11]BF4 and trans-[12]BF4 were determined by X-ray diffraction showing significant differences of comparable metric parameters in the theophylline-derived five-membered diaminoheterocycles. No interaction of the N-allyl substituents with the metal center was observed.

Shedding light on the bimolecular interactions of Cafaminol and human serum albumin: spectroscopic characterization and in-silico investigation

Alavianmehr, Mohamad Mehdi,Behrouz, Somayeh,Mohammad-Aghaie, Delara,Parvizi, Negar,Soltani Rad, Mohammad Navid

, (2020)

Cafaminol, also known as methylcoffanolamine, is a vasoconstrictor and anticatarrhal of the methylxanthine family, which is used as a nasal decongestant. This study aimed to investigate the interaction mechanisms of human serum albumin (HSA) with Cafaminol, through several spectroscopic (fluorescence quenching, UV-visible absorption, and circular dichroism (CD) spectroscopies) and molecular modeling techniques. Stern-Volmer plots were employed to specify the fluorescence quenching mechanism, while the simulation methods were utilized to deduce the approximate binding position of Cafaminol on HSA. On the other hand, thermodynamic parameters, enthalpy and entropy changes, were determined to be, respectively, ?105.88 (kJ mol?1) and ?282.34 (J mol?1 K?1), using the Van't Hoff equation and analyzed later to specify the main acting forces between Cafaminol and HSA. Overall results revealed the binding of Cafaminol to the site I of HSA, as a result of an enthalpy-driven process, mainly through the van der Waals and hydrogen bonding interactions. Static quenching mechanism was found to be responsible for the fluorescence quenching of HSA in the Cafaminol presence, while the number of binding sites and apparent binding constant were measured accordingly. Docking results proposed that Cafaminol and HSA interact with a binding free energy (ΔG) of ?6.5 kcal mol?1 Communicated by Ramaswamy H. Sarma.

Synthetic Transformations of Sesquiterpene Lactones. 11.* Conjugates Based on Caffeine and Eudesmanolides with N-Containing Linkers

Reshetnikov,Patrushev,Shults

, p. 855 - 860 (2020)

8-(Aminoalkylamino)caffeine or 8-(piperazinyl)caffeine were formed in high yields by reacting 8-bromo- or 8-chlorocaffeine with linear and cyclic diamines using microwave-assisted organic synthesis. These amines were highly reactive in Michael reactions with sesquiterpene lactones containing active methylene groups. Conjugates with caffeine and eudesmanolide moieties bonded by a N-containing linker were synthesized.

Radical Carbonyl Umpolung Arylation via Dual Nickel Catalysis

Huang, Huan-Ming,Bellotti, Peter,Erchinger, Johannes E.,Paulisch, Tiffany O.,Glorius, Frank

supporting information, p. 1899 - 1909 (2022/02/01)

The formation of carbon-carbon bonds lies at the heart of synthetic organic chemistry and is widely applied to construct complex drugs, polymers, and materials. Despite its importance, catalytic carbonyl arylation remains comparatively underdeveloped, due

8-Ethynylxanthines as promising antiproliferative agents, angiogenesis inhibitors, and calcium channel activity modulators

Arsenyan, Pavel,Vasiljeva, Jelena,Domracheva, Ilona,Kanepe-Lapsa, Iveta

, p. 776 - 785 (2020/07/27)

[Figure not available: see fulltext.] Synthetic procedures for the preparation of 8-ethynylxanthines by treating 8-bromocaffeine and 8-bromopentoxifylline with terminal acetylenes were elaborated. Certain ethynylxanthine derivatives exhibit high in vitro antiproliferative activity against a panel of cancer cell lines, matrix metalloproteinase and in vitro angiogenesis inhibitory activity. Ca2+ channel blocking and agonist activity of the synthesized ethynylxanthines was discussed based on data obtained on the H9C2, SH-SY5Y, and A7R5 cell lines.

Organic semiconductor compounds comprising caffeine and Organic solar cell comprising the same

-

Paragraph 0120-0124, (2020/04/22)

The present invention relates to an organic semiconductor compound comprising caffeine and an organic solar cell comprising the same, wherein and the organic semiconductor compound of the present invention can introduce caffeine into an end group, thereby

Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes

Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.

supporting information, p. 417 - 428 (2019/02/14)

Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.

General Entry into o-,o′-Heteroatom-Linked N-(Hetero)aryl-Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

Garzón, Miguel,Arce, Elsa M.,Reddy, Raju Jannapu,Davies, Paul W.

, p. 1837 - 1843 (2017/06/09)

A general redox-neutral approach into the o-,o′-heteroatom-linked N-(hetero)aryl-imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl)-pyridinium-N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores. (Figure presented.).

ETHYNYLXANTHINES, PREPARATION AND USE AS CALCIUM ION CHANNEL MODULATORS

-

Page/Page column 11; 12, (2016/10/27)

The present invention relates to novel pharmaceutical compounds, which exhibit ability to act as calcium ion channel modulators, methods for their synthesis and the treatment and/or prevention of various diseases and disorders including deregulated calcium ion channel activity.

Aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide mediated by anthraquinone-2-carboxylic acid

Tanaka, Masanori,Kamito, Yuji,Lei, Cui,Tada, Norihiro,Itoh, Akichika

, p. 5886 - 5888 (2015/11/02)

We developed the aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide in the presence of anthraquinone-2-carboxylic acid under visible light irradiation.

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