1086-80-2

Basic information

• Product Name: LUMICHROME
• Synonyms: LUMICHROME;7,8-DIMETHYLALLOXAZINE;7,8-Dimethylbenzo[g]pteridine-2,4-diol;Benzo[g]pteridine-2,4(1H,3H)-dione, 7,8-dimethyl-;Lumichrome (I);Riboflavin lumichrome;7,8-dimethylbenzo[g]pteridine-2,4(1H,3H)-dione;7,8-Dimethylbenzo[g]pteridine-2,4(3H,10H)-dione
• CAS NO: 1086-80-2
• Molecular Formula: C₁₂H₁₀N₄O₂
• Molecular Weight: 242.23
• EINECS: 214-120-8
• Mol File: 1086-80-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 385.06°C (rough estimate)
• Flash Point: °C
• Appearance: solid
• Density: 1.2532 (rough estimate)
• Refractive Index: 1.6081 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated)
• PKA: 10.02±0.70(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• Merck: 13,5620
• CAS DataBase Reference: LUMICHROME(CAS DataBase Reference)
• NIST Chemistry Reference: LUMICHROME(1086-80-2)
• EPA Substance Registry System: LUMICHROME(1086-80-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 1086-80-2(Hazardous Substances Data)

Usage

Description

LUMICHROME is a compound derived from Riboflavin (R415000), a vital vitamin that plays a crucial role in maintaining cellular function and overall health in both humans and animals. It is characterized by its blue fluorescence, which is a result of the photolysis of riboflavin in either an acidic or neutral solution. LUMICHROME is a solid substance with various applications across different industries.

Uses

Used in Dyes and Metabolites Industry:
LUMICHROME is used as a dye for its blue fluorescence property, which is particularly useful in creating visually appealing and vibrant colors in various applications.
Used in Pharmaceutical and Biomedical Applications:
LUMICHROME is used as a metabolite in the study and treatment of various health conditions, given its connection to Riboflavin, a vital component for cellular function and health.
Used in Research and Development:
LUMICHROME is utilized as a research compound for studying the properties and effects of Riboflavin and its derivatives, contributing to the advancement of knowledge in the fields of chemistry, biology, and medicine.

Purification Methods

Recrystallise lumichrome twice from glacial AcOH and dry it at 100o in a vacuum. [Cresswell & Wood J Chem Soc 4768 1960, Beilstein 26 III/IV 2538.]

InChI:InChI=1/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)

Upstream product

• 80144-39-4 6,7-dimethyl-3-ethoxycarbonylaminoquinoxaline-2-carboxamide 
• 83-88-5 riboflavin 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 1088-56-8 lumiflavin 
• 21079-31-2 carboxylmethylflavin 
• 4250-90-2 Formylmethylflavin 
• 3237-50-1 5,5-dihydroxy-pyrimidine-2,4,6-trione 
• 3483-12-3 diothiothreitol 
• 183492-69-5 4,5-dimethyl-2-nitro-N-benzylaniline 
• 3240-72-0 5,6-diaminouracil 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 699-40-1 5,5-Dichloro-barbituric acid 
• 67-52-7 BARBITURIC ACID 

Downstream Products

• 14684-48-1 1,3-dimethyllumichrome 
• 874499-50-0 6,7-dimethyl-quinoxalin-2-ylamine 

Related news

Photophysics of LUMICHROME (cas 1086-80-2) on cellulose08/13/2019

Lumichrome samples were prepared by depositing lumichrome on cellulose from methanol solutions. Diffuse reflectance absorption bands at 354 and 388 nm (shoulder) and the fluorescence band at 460 nm similar to those observed in polar solvents were attributed to a π→π∗ transition. The emission ...detailed

Relevant articles and documents

-

-

Effect of phosphate buffer on the complexation and photochemical interaction of riboflavin and caffeine in aqueous solution: A kinetic study

A study of the photodegradation of 5 × 10-5 M riboflavin (RF) in 0.2-1.0 M phosphate buffer in the presence and absence of 2.50 × 10-4 M caffeine at pH 6.0-8.0 has been carried out. RF in phosphate buffer is photodegraded simultaneously by normal photolysis (photoreduction) and photoaddition reactions giving rise to lumichrome (LC) and cyclodehydroriboflavin (CDRF) as the main final products, respectively. RF and its photoproducts, formylmethylflavin (FMF), lumiflavin (LF), LC and CDRF in degraded solution have been determined by a specific multicomponent spectrophotometric method with an accuracy of ±5%. The apparent first-order rate constants for the photodegradation of RF and for the formation of LC and CDRF are 5.47-15.05 × 10-3 min-1, 1.06-8.30 × 10-3 min-1 and 4.31-8.05 × 10 -3 min-1, respectively. An increase in phosphate concentration leads to an increase in the rate of formation of CDRF and alters the photodegradation of RF in favor of the photoaddition reaction. This photoaddition reaction is further enhanced in the presence of caffeine which results in a further decrease of the fluorescence of RF in phosphate buffer. Caffeine may facilitate the photoaddition reaction by suppression of the photoreduction pathway of RF.

-

-

-

-

Effect of ph, buffer, and viscosity on the photolysis of formylmethylflavin: A kinetic study

The kinetics of the photolysis of formylmethylflavin, a major intermediate product in the aerobic and anaerobic photolysis of riboflavin, was studied in the pH range 2.0-11.0. Formylmethylflavin and its photoproducts, lumichrome and lumiflavin, were determined in degraded solutions using a specific multicomponent spectrophotometric method. The photolysis of formylmethylflavin in alkaline medium takes place by first-order kinetics and the rate constants (kobs) at pH 7.5-11.0 range from 0.27×10-4 to 3.88×10-4 and 0.36×10-4 to 5.63×10-4s-1 under aerobic and anaerobic conditions respectively. In acid medium, the photolysis involves a second-order mechanism and the rate constants at pH 2.0-7.0 range from 1.37 to 2.11 and 2.03 to 2.94M-1s-1 under aerobic and anaerobic conditions respectively. The rate-pH profiles for the photolysis reactions indicate the highest rate of formylmethylflavin degradation is at ～pH 4 and above pH 10. In the alkaline region, the increase in rate with pH is due to higher reactivity of the flavin triplet state. The photolysis of formylmethylflavin is catalyzed by phosphate ions and is affected by the solvent viscosity.

-

-

-

-

Synthesis of quinoxalines under focussed microwave irradiation

Quinoxalines were obtained by the condensation of α-diones with o-diaminobenzenes without solvent under focussed microwave irradiation.

A study of photochemistry of flavins in pyridine and with a donor.

-

Organocatalytic Dakin oxidation by nucleophilic flavin catalysts

Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

-

-

Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine

Photoirradiation in the presence of riboflavin led to guanine oxidation and the formation of imidazolone. Meanwhile, riboflavin itself was degraded by ultraviolet light A (UV-A) and visible light (VIS) radiation, and the end product was lumichrome. VIS radiation in the presence of riboflavin oxidized guanine similarly to UV-A radiation. Although UV-A radiation with lumichrome oxidized guanine, VIS radiation with lumichrome did not. Thus, UV-A radiation with riboflavin can oxidize guanine even if riboflavin is degraded to lumichrome. In contrast, following VIS radiation degradation of riboflavin to lumichrome, VIS radiation with riboflavin is hardly capable of oxidizing guanine. The consequences of riboflavin degradation and guanine photooxidation can be extended to flavin mononucleotide and flavin adenine dinucleotide. In addition, we report advanced synthesis; carboxymethylflavin was obtained by oxidation of formylmethylflavin with chlorite and hydrogen peroxide; lumichrome was obtained by heating of formylmethylflavin in 50% AcOH; lumiflavin was obtained by incubation of formylmethylflavin in 2 M NaOH, followed by isolation by step-by-step concentration.

Photolysis of carboxymethylflavin in aqueous and organic solvent: A kinetic study

This is the first study on the photolysis of carboxymethylflavin (CMF), an intermediate in the photolysis of riboflavin (RF). CMF is photodegraded by removal of side-chain to lumichrome (LC) in acid solution and to LC and lumiflavin (LF) in alkaline solution. It also undergoes alkaline hydrolysis to 1,2-dihydro-1-methyl-2-keto-3-quinoxaline carboxylic acid (KA) and 1,2,3,4-tetrahydro-1-methyl-2,3-dioxoquinoxaline (DQ) by cleavage of isoalloxazine ring. CMF degrades to LC in organic solvents. The formation of LC in acid solution and organic solvents takes place by second-order reaction and those of LC, LF, KA and DQ in alkaline solution by first-order reactions. The values of second-order rate constants for the photolysis of CMF at pH 2.0 to 7.0 are in the range of 1.13 to 2.45 M-1 s-1 and those of first-order rate constants (kobs) at pH 8.0-12.0 from 1.53 to 4.18 × 10-4 s-1 and for the formation of photoproducts from 0.37 to 16.6 × 10-5 s-1. The photolysis of CMF is enhanced, with pH, in the alkaline region since the excited state is sensitive to alkaline hydrolysis. The photolysis and fluorescence quantum yields of CMF in aqueous and organic solvents have been reported. CMF and photoproducts have been assayed spectrofluorimetrically. The mode of CMF photolysis is discussed.