Riboflavin, 2',3',4',5'-tetraacetate

Base Information

• Chemical Name: Riboflavin, 2',3',4',5'-tetraacetate
• CAS No.: 752-13-6
• Molecular Formula: C25H28 N4 O10
• Molecular Weight: 544.518
• European Community (EC) Number: 212-032-4
• DSSTox Substance ID: DTXSID10996662
• Nikkaji Number: J3.450.976J
• ChEMBL ID: CHEMBL233068
• Mol file: 752-13-6.mol

Synonyms:2,3,4,5-Tetra-O-acetyl-1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol;Riboflavin, 2',3',4',5'-tetraacetate;752-13-6;[2,3,4-triacetyloxy-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)pentyl] acetate;Riboflavine tetraacetate;Vitamin B2 tetraacetate;Tetra-O-acetylriboflavine;2',3',4',5'-Tetra-O-acetylriboflavin;Riboflavine, 2',3',4',5'-tetraacetate;Tetraacetylriboflavine;CHEMBL233068;DTXSID10996662;STL068827;AKOS000503328;AKOS024266897;2',3',4',5'-Tetraacetyl-lactoflavin;2,3,4,5-Tetra-O-acetyl-1-deoxy-1-(4-hydroxy-7,8-dimethyl-2-oxobenzo[g]pteridin-10(2H)-yl)pentitol;2,3,4,5-Tetra-O-acetyl-1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol #

Chemical Property of Riboflavin, 2',3',4',5'-tetraacetate

Chemical Property:

• Melting Point: 238 °C
• PKA: 9.83±0.70(Predicted)
• PSA: 186.10000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 1.02030
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 13
• Exact Mass: 544.18054310
• Heavy Atom Count: 39
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: riboflavin tetraacetate is a skin-conditioning agent, it is a vitamin B2 derivative.

Technology Process of Riboflavin, 2',3',4',5'-tetraacetate

There total 17 articles about Riboflavin, 2',3',4',5'-tetraacetate 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: 99.0%

acetic anhydride (108-24-7) + riboflavin (83-88-5,42880-33-1) → tetra-O-acetyl riboflavin (752-13-6)

Guidance literature:

With pyridine; at 120 ℃; for 0.333333h;

DOI:10.1002/chem.201800231

Reference yield: 80.0%

acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) + riboflavin (83-88-5,42880-33-1) → tetra-O-acetyl riboflavin (752-13-6)

Guidance literature:

With perchloric acid; at 45 ℃; for 0.666667h; Schlenk technique;

DOI:10.1007/s10895-017-2135-x

Reference yield: 73.0%

acetic anhydride (108-24-7) + riboflavin (83-88-5,482-11-1,482-12-2,3687-62-5,5978-87-0,13123-37-0,33210-89-8,35919-91-6,53187-51-2,53187-52-3,135681-43-5,42880-33-1) → riboflavin 2',3',4',5'-tetra-acetate (752-13-6,5978-88-1,53130-70-4,53130-71-5)

Guidance literature:

With sulfuric acid; acetic acid; at 80 ℃;

DOI:10.1002/chem.202100053

upstream raw materials:

acetic anhydride

10-L-arabitol-5-yl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

5-(2-amino-4,5-dimethyl-anilino)-5-deoxy-L-arabitol

5-(4,5-dimethyl-2-phenylazo-anilino)-5-deoxy-L-arabitol

Downstream raw materials:

riboflavin

7,8-dimethyl-10-(tetra-O-acetyl-DL-arabitol-1-yl)-10H-benzo[g]pteridine-2,4-dione

3-Methyl-tetra-O-acetyl-riboflavin

Refernces

Biosensor-Based Determination of Riboflavin in Milk Samples

10.1021/ac034876a

The study presents the development of a biosensor-based assay for the quantification of riboflavin (Rf) in milk samples using surface plasmon resonance (SPR) technology. The assay involves the indirect measurement of Rf by detecting the excess of riboflavin binding protein (RBP) that remains free after complexation with Rf molecules originally present in the sample. The sensor chip is modified with covalently immobilized Rf to bind the excess RBP. The method involves a chemical modification to introduce a reactive ester group on the Rf molecule for immobilization on the chip surface. Calibration solutions are prepared by mixing Rf standard solutions with an optimized concentration of RBP, and the Rf content in milk samples is measured by comparing the response against the calibration. The results are comparable to those obtained from an official HPLC-fluorescence procedure, with a limit of quantification determined to be 234 μg/L and a limit of detection to 70 μg/L. The study demonstrates the potential of SPR-based biosensors as a competitive alternative to traditional analytical techniques for the determination of riboflavin in food samples.