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

3-benzyl-2',3',4',5'-tetraacetylriboflavin

Refernces

• 1、 Banekovich, Christian,Ott, Ingo,Koch, Thao,Matuszczak, Barbara,Gust, Ronald. "Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates". . p. 683 - 687. Retrieved 2007.
• 2、 Fukuzumi, Shunichi,Yasui, Kiyomi,Suenobu, Tomoyoshi,Ohkubo, Kei,Fujitsuka, Mamoru,Ito, Osamu. "Efficient catalysis of rare-earth metal ions in photoinduced electron-transfer oxidation of benzyl alcohols by a flavin analogue". . p. 10501 - 10510. Retrieved 2001.
• 3、 Cheng, Pi,Dong, Zhuang,Fan, Shulin,Huang, Pilin,Song, Yunfei,Wang, Lin,Wang, Xinhao,Zeng, Jianguo. "Visible-light promoted allylation of N-substituted tetrahydroisoquinoline using riboflavin tetra-acetate as photocatalyst". supporting information. . Retrieved 2021/08/04.
• 4、 Chouhan, Dwarika Kumar,Harale, Bhaiyyasaheb,Khedkar, Vijay,Kidwai, Saqib,Ojha, Divya,Rode, Ambadas B.,Singh, Manisha,Singh, Ramandeep. "Synthesis and evaluation of antimycobacterial activity of riboflavin derivatives". supporting information. . Retrieved 2021/07/16.