Caffeine

Base Information

• Chemical Name: Caffeine
• CAS No.: 58-08-2
• Deprecated CAS: 71701-02-5,95789-13-2,95789-13-2
• Molecular Formula: C8H10N4O2
• Molecular Weight: 194.193
• Hs Code.: 29393000
• European Community (EC) Number: 200-362-1,693-596-2
• ICSC Number: 0405
• NSC Number: 755917,5036
• UN Number: 1544
• UNII: 3G6A5W338E
• DSSTox Substance ID: DTXSID0020232
• Nikkaji Number: J2.330B
• Wikipedia: Caffeine
• Wikidata: Q60235
• NCI Thesaurus Code: C328
• RXCUI: 1886
• Pharos Ligand ID: K2U7RXHYNVYT
• Metabolomics Workbench ID: 37886
• ChEMBL ID: CHEMBL113
• Mol file: 58-08-2.mol

Synonyms:1H-Purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl-;1,3,7-Trimethyl-2,6-dioxopurine;1,3,7-Trimethylxanthine;3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;7-Methyltheophylline;Alert-Pep;Asia migrine;DHCplus;Durvitan;Guaranine;Koffein;Mateina;Methyltheobromine;Midron extra;Miudol;Phensal;Refresh'n;SK 65 Compound;Shape Plus;StayAlert;Theine;

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Caffeine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 234-236.5 °C(lit.)
• Refractive Index: 1.6590 (estimate)
• Boiling Point: 416.789 °C at 760 mmHg
• PKA: pKa 0.6 (Uncertain)
• Flash Point: 205.867 °C
• PSA: 61.82000
• Density: 1.45 g/cm³
• LogP: -1.02930
• Storage Temp.: 2-8°C
• Solubility.: Sparingly soluble in water, freely soluble in boiling water, slightly soluble in ethanol (96 per cent). It dissolves in concentrated solutions of alkali benzoates or salicylates.
• Water Solubility.: 20 g/L (20 ºC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 194.08037557
• Heavy Atom Count: 14
• Complexity: 293
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T,F
• Statements: 22-25-39/23/24/25-23/24/25-11
• Safety Statements: 16-36/37-45-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Drug Classes: CNS Stimulants, Xanthine Derivatives
• Canonical SMILES: CN1C=NC2=C1C(=O)N(C(=O)N2C)C
• Recent ClinicalTrials: A Study to Learn How Well a Single Dose of the Study Treatment Naproxen Sodium and Caffeine Combined in One Tablet (Fixed-dose Combination) Works to Relieve Pain After Dental Surgeries Compared to the Single Ingredients and to Placebo
• Recent EU Clinical Trials: An Open-label Drug-Drug Interaction Study to Assess the Effects of Nemolizumab on Cytochrome P450 Substrates in Subjects with Moderate-to-Severe Atopic Dermatitis
• Recent NIPH Clinical Trials: Study of the effect of caffeine consumption on the efficiency of surgical closure
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system and cardiovascular system. This may result in insomnia, excitement, tachycardia and polyuria.
• Description: Caffeine is an alkaloid purine belonging to the group of organic compounds called methylxanthines. Pure caffeine is a white, crystalline, bitter-tasting compound. Caffeine is found in a number of plants, principally coffee and tea plants, as well as cola and cacao nuts. In plants, caffeine functions as a natural pesticide to deter insects. Caffeine is a purine alkaloid commonly found in coffee and tea. Several in vivo studies have demonstrated that topical and oral administration of caffeine exerts a photoprotective effect through various mechanisms. Specifically, caffeine has been demonstrated to induce apoptosis in DNA damaged epidermal cells and tumors while sparing normal tissue. Mouse models demonstrate that this apoptotic effect is secondary to increased expression of wild-type p53, a tumor suppressor gene that is commonly mutated in UV-related skin cancers. Moreover, caffeine also has a sunscreen-like effect and inhibits formation of UVB-induced thymine dimers and sunburn skin lesions.
• Physical properties: Appearance: odorless silky needle-like crystal or crystal powder with the color of white or a little yellowish green. Solubility: weathering, easily dissolved in water or chloroform and slightly soluble in water, ethanol, or acetone, very slightly dissolved in ether. Melting point: 235–238?°C.
• Uses: Caffeine has widespread therapeutic use. It is widely used in headache (migraine) remedies such as aspirin and other analgesics. Caffeine is a mild vasoconstrictor and its ability to constrict blood vessels serving the brain explains its use to relieve headache. Caffeine is a common substance in medications to treat apnea in premature infants. Apparently, the area of the brain controlling respiration in premature infants is not fully developed and caffeine helps to stimulate this portion of the brain. The combination of caffeine and ephedrine is used in dietary and athletic supplements, and their role as appetite suppressant and energy boosters has been extensively studied. Caffeine is consumed in coffee, tea, cocoa,chocolate, and soft drinks. It occurs naturallyin the leaves of coffee, tea, and mate and in ′cola nuts. It is used in medicine and found inmany drugs. It is used as a cardiac stimulant. caffeine has a lipolytic effect on fatty cells, able to break down lipids and release fatty acids. given this ability and its draining properties, caffeine is used for skin firming and tightening. It is often incorporated into body product formulations targeting cellulite and slimming, as well as in eye creams that claim to reduce puffiness. Among its constituents are tannin and the alkaloid methylxanthine. Caffeine is a bitter-tasting, odorless white powder that occurs naturally in coffee, cola, guana paste, kola nuts, and tea. It is obtained as a by-product of decaffeinated coffee. Caffeine is a white powder or needles that are odorless and have a bitter taste. it occurs naturally in tea leaves, coffee, cocoa, and cola nuts. it is a food additive used in soft drinks for its mildly stimulat- ing effect and distinctive taste note. it is used in cola-type beverages and is optional in other soft drinks up to 0.02%. Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants. In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Caffeine is a cardiac and respiratory stimulant; diuretic. Caffeine is toxic at sufficiently high doses. CNS stimulant respiratory stimulant;adenosine receptors antagonist
• Indications: This product is included in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the European Pharmacopoeia (9.0th ed.), the Indian Pharmacopoeia (2010), and the International Pharmacopoeia (5th ed.). Commonly used dosage forms of caffeine include tablet, powder, and injection. Mainly used dosage forms in the market include caffeine citrate tablets, amidopyrine caffeine tablets, amidopyrine caffeine, children acetaminophen aspirin caffeine tablets, ergotamine caffeine tablets, caffeine sodium benzoate injection, cafe bromine agent, etc.
• Therapeutic Function: Neurotropic, Central stimulant
• Clinical Use: The commonly used clinical preparations include caffeine sodium benzoate and ergotamine caffeine. The preparation of caffeine sodium benzoate (injection) is constituted of 0.12?g/ml of caffeine, 0.13?g/ml of sodium benzoate, and cafe bromine mixture (oral liquid). Clinically, it can be used for migraine headaches, cerebral artery dilated headache, or headache caused by histamine. However, it is invalid in the prevention of headaches. The adverse reactions include nausea, vomiting, abdominal pain, and fatigue. Other common symptoms include numbness and tingling of the hands, toes, and face and swelling of the foot and lower limb. Overdose causes severe poisoning, mental disorder, ataxia, convulsions, gray chills of the hand and foot, sensory disturbance, and even death due to coma and respiratory paralysis. Caffeine citrate preparation, including injection and oral solution, is the only internationally approved drug for the treatment of premature infant apnea.

Technology Process of Caffeine

There total 132 articles about Caffeine 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: 100.0%

methyl bromide (74-83-9) + xanthin (69-89-6,6053-41-4) → 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2)

Guidance literature:

With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide; In dichloromethane; 1)room temp. 12h 2)reflux 3h;

Reference yield: 98.4%

theophylline sodium salt (3485-82-3) + carbonic acid dimethyl ester (616-38-6) → 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; ethylene glycol; at 135 ℃; for 4h; Autoclave; Green chemistry;

DOI:10.1002/jccs.201900432

Reference yield: 98.0%

methyl bromide (74-83-9) + theophylline (58-55-9,75448-53-2) → 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2) + 3-benzyladenine (7280-81-1)

Guidance literature:

With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide; In dichloromethane; 1)20 deg C, 12h 2)40 deg C, 3h;

upstream raw materials:

theophylline

methyl p-toluene sulfonate

dimethyl sulfate

methanol

Downstream raw materials:

4,5-dimethoxy-1,3,7-trimethyl-tetrahydro-purine-2,6,8-trione

8-acetoxymercuri-caffeine

caffeidine

1,3-dimethylalloxan

Refernces

• 1、 Yang, Shu-Zhen,Dong, Zhi-Qiang,Yin, Cheng-Cheng,Yue, Hui-Juan,Gao, Wei-Wei,Yang, Feng-Ke. "Green synthesis of caffeine based on methylating reagent dimethyl carbonate and environmental friendly separating method". . p. 1715 - 1720. Retrieved 2020/03/27.
• 2、 Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei. "Dehydroxymethylation of alcohols enabled by cerium photocatalysis". supporting information. p. 10556 - 10564. Retrieved 2019/08/20.