752-13-6

Usage

Uses

riboflavin tetraacetate is a skin-conditioning agent, it is a vitamin B2 derivative.

Upstream product

• 108-24-7 acetic anhydride 
• 83-88-5 riboflavin 
• 33210-89-8 arabinoflavin 
• 752-13-6 7,8-dimethyl-10-(tetra-O-acetyl-L-arabitol-1-yl)-10H-benzo[g]pteridine-2,4-dione 
• 5978-88-1 Tetraacetyl-D-arabinoflavin 
• 64-19-7 acetic acid 
• 83-88-5 riboflavin 
• 67-52-7 BARBITURIC ACID 
• 18717-85-6 1,5-dihydroriboflavin-2',3',4',5'-tetraacetate 
• 113473-93-1 5-(4,5-dimethyl-2-phenylazo-anilino)-5-deoxy-L-arabitol 
• 64598-64-7 5-(2-amino-4,5-dimethyl-anilino)-5-deoxy-L-arabitol 
• 13123-37-0 10-L-arabitol-5-yl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione 

Downstream Products

• 83-88-5 riboflavin 
• 752-13-6 7,8-dimethyl-10-(tetra-O-acetyl-DL-arabitol-1-yl)-10H-benzo[g]pteridine-2,4-dione 
• 21066-33-1 3-Methyl-tetra-O-acetyl-riboflavin 
• 1260509-81-6 3-benzyl-2',3',4',5'-tetraacetylriboflavin 
• 21066-33-1 3-methyl-tetraacetylriboflavin 
• 28714-80-9 3-carboxymethylriboflavin 

Relevant academic research and scientific papers

Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin

The riboflavin dye 2,3,4,5-tetra-O-acetyl-1-[3-(6-bromohexyl)-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-1-deoxypentitol and its pyridinium salt were synthesized, and studied by absorption and fluorescence spectroscopy in solutions and

Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates

A series of novel dexibuprofen derivatives covalently linked via alkylene spacers of variable length to tetraacetylated riboflavin have been developed. The target compounds became accessible by reaction of the chloromethyl ester of dexibuprofen with tetraacetylriboflavin (compound 7) or by synthesis of the appropriate N3-(ω-iodoalkyl)-2′,3′,4′,5′-Tetraacetylri boflavin followed by treatment with dexibuprofen (derivatives 8-11), respectively. Biological screening revealed that the target compounds exhibit antiproliferative effects on MCF-7 breast cancer and HT-29 colon carcinoma cells with IC50 values in the range of 8-15 μM. Enzymatic studies on human platelets indicated significant COX-1 inhibitory activities of the target compounds.

Formation of a Transient Radial Ion Pair in the Reactions of 1,5-Dihydroflavin with Hydride Acceptors

The formation of a transient radical ion pair has been detected directly in the reactions of 1,5-dihydroriboflavin-2',3',4',5'-tetraacetate (FIH2) with hydride acceptors (tetracyano-p-quinodimethane, tetracyanoethylene and p-benzoquinone derivatives) in deaerated acetonitrile, providing unequivocal evidence for an electron transfer pathway in the overall two-electron redox reactions of FIH2 with hydride acceptors.

Efficient catalysis of rare-earth metal ions in photoinduced electron-transfer oxidation of benzyl alcohols by a flavin analogue

A flavin analogue (riboflavin-2′,3′,4′,5′-tetraacetate, Fl) forms the 1:1 and 1:2 complexes with rare-earth metal ions. The largest formation constants K1 and K2 for the 1:1 and 1:2 complexes between Fl and Sc3+ are determined as K1 = 3.1 × 104 M-1 and K2 = 1.4 × 103 M-1, respectively. The complexation of Fl with rare-earth metal ions results in blue shifts of the fluorescence maximum, shortening of the fluorescence lifetime, and more importantly the change in the lowest excited state from the n,π* triplet state of Fl to the π,π* singlet states of Fl-rare-earth metal ion complexes as indicated by the disappearance of the triplet-triplet (T-T) absorption spectrum of Fl by the complexation with metal ions. The strong complex formation between Fl and rare-earth metal ions enhances the oxidizing ability of the excited state of Fl as indicated by the significant acceleration in the fluorescence quenching rates of Fl-rare earth metal ion complexes via electron transfer from electron donors (e.g., alkylbenzenes) as compared to those of uncomplexed Fl. The one-electron reduction potential of the singlet excited state of the 1:2 complex between Fl and Sc3+, 1(Fl-2Sc3+)* (* denotes the excited state), is positively shifted by 780 mV as compared to 1Fl*. Such a remarkable enhancement of the redox reactivity of 1(Fl-2Sc3+)* as compared to that of 1Fl* makes it possible to oxidize efficiently p-chlorobenzyl alcohol to p-chlorobenzaldehyde by 1(Fl-2Sc3+)*, although no photooxidation of p-chlorobenzyl alcohol by Fl occurred in deaerated MeCN. The quantum yield for the photooxidation of p-chlorobenzyl alcohol by Fl-2Sc3+ is the largest among various Fl-metal ion complexes. A comparison of the observed rate constant derived from the dependence of the quantum yield on the concentration of p-chlorobenzyl alcohol with the fluorescence quenching rate constant by electron transfer from the alcohol and the direct detection of radical intermediates reveal that the photooxidation proceeds via electron transfer from p-chlorobenzyl alcohol to 1(Fl-2Sc3+)*. Under an atmospheric pressure of oxygen, the photooxidation of p-methoxybenzyl alcohol by oxygen proceeds efficiently in the presence of Fl-Lu3+ which acts as an efficient photocatalyst. No photodegradation was observed in the case of the Fl-Lu3+ complex, whereas the facile photodegradation of Fl-Mg2+ has precluded the efficient photocatalytic oxidation of the alcohol by oxygen.

(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity

The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.

Synthesis and evaluation of antimycobacterial activity of riboflavin derivatives

The riboflavin biosynthetic pathway is a promising target for the development of novel antimycobacterial drugs given the lack of riboflavin transporter in M. tuberculosis. Herein, a series of riboflavin derivatives was designed, synthesized and screened for their antimycobacterial and antibacterial activity. The compounds 1a, 1b, 2a, 3a and 5a displayed noticeable antitubercular activity against M. tuberculosis with minimum inhibitory concentration (MIC99) in the range of 6.25 to 25 μM. The lead compound 5a had a selectivity index of 10.7 in the present study. The compounds 2a, 2b, 2c, 4c and 4d showed relatively low to moderate antibacterial activity (MIC = 100–200 μM) against gram-positive strains. Notably, the compounds do not show any inhibition against gram-negative strains even at 200 μM concentration. Further, molecular docking and binding experiments with representative flavin mononucleotide (FMN) riboswitch suggested that the riboflavin analogs exhibited antimycobacterial activity plausibly through FMN riboswitch-mediated repression of riboflavin biosynthesis. In addition to FMN riboswitch, flavoproteins involved in the flavin biosynthesis could also be target of riboflavin derivatives. In conclusion, the potency and low toxicity of riboflavin analogs particularly 5a (MIC99 = 6.25) make it a lead compound for the synthesis of new analogs for antimycobacterial therapy.

Visible-light promoted allylation of N-substituted tetrahydroisoquinoline using riboflavin tetra-acetate as photocatalyst

Riboflavin (RF) and relative derivatives are important coenzyme of some redox enzymes controlling the growing development of plants by harvesting light. The unique isoalloxazine structure unit with special photoredox capacity makes it applicable to induce

Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles

Benzothiazoles are synthesized from thiobenzanilides using riboflavin as a photosensitizer and potassium peroxydisulfate as a sacrificial oxidizing agent under visible light irradiation. The methodology accepts a broad range of functional groups and affords the 2-substituted benzothiazoles by transition-metal-free organic photoredox catalysis under very mild conditions.

Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols

Riboflavin-derived photocatalysts have been extensively studied in the context of alcohol oxidation. However, to date, the scope of this catalytic methodology has been limited to benzyl alcohols. In this work, mechanistic understanding of flavin-catalyzed oxidation reactions, in either the absence or presence of thiourea as a cocatalyst, was obtained. The mechanistic insights enabled development of an electrochemically driven photochemical oxidation of primary and secondary aliphatic alcohols using a pair of flavin and dialkylthiourea catalysts. Electrochemistry makes it possible to avoid using O2 and an oxidant and generating H2O2 as a byproduct, both of which oxidatively degrade thiourea under the reaction conditions. This modification unlocks a new mechanistic pathway in which the oxidation of unactivated alcohols is achieved by thiyl radical mediated hydrogen-atom abstraction.

Selenium-containing compound and use thereof

The invention relates to an application of riboflavin selenium derivative shown in the description in preparing cancer chemopreventive agent. The compound is capable of significantly inducing the expression of quinone reductase and without significant cytotoxic effect under enzyme-induced activity concentration conditions, and can be used as effective cancer chemopreventive and therapeutic agent.