deoxyfructosazine

Base Information

• Chemical Name: deoxyfructosazine
• CAS No.: 17460-13-8
• Molecular Formula: C12H20 N2 O7
• Molecular Weight: 304.3
• Hs Code.: 29072990
• Mol file: 17460-13-8.mol

Synonyms:1,2,3,4-Butanetetrol,1-[5-(2,3,4-trihydroxybutyl)pyrazinyl]-, [1R-[1R*(2S*,3R*),2S*,3R*]]-;1,2,3,4-Butanetetrol, 1-[5-(D-erythro-2,3,4-trihydroxybutyl)pyrazinyl]-,D-arabino- (6CI,8CI); 1,2,3,4-Butanetetrol,1-[5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazinyl]-, (1R,2S,3R)- (9CI);2,5-Deoxyfructosazine; 2-(D-arabino-1',2',3',4-Tetrahydroxybutyl)-5-(D-erythro-2'',3'',4''-trihydroxy-butyl)pyrazine;2-(D-arabino-Tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)pyrazine;D-Fructosazine, deoxy-; Deoxyfructosazine; NSC 270912

Chemical Property of deoxyfructosazine

Chemical Property:

• Vapor Pressure: 2.8E-21mmHg at 25°C
• Melting Point: 157-160°C
• Boiling Point: 712°Cat760mmHg
• PKA: 11.86±0.20(Predicted)
• Flash Point: 384.4°C
• PSA: 186.56000
• Density: 1.582g/cm³
• LogP: -4.02680
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly, Sonicated)

Purity/Quality:

98% ^*data from raw suppliers

2,5-Deoxyfructosazine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2,5-Deoxyfructosazine is a pyrazine derivative that can be found in cured tobacco and is used as a flavoring agent in the food and tobacco industry. Pyrazines, including 2,5-deoxyfructosazine, can be produced either by pyrolytic decomposition of natural compounds or by the reaction of sugars with alcoholic ammonia. 2,5-Deoxyfructosazine is also formed by the breakdown of D-glucosamine at neutral pH. Like glucosamine, 2,5-deoxyfructosazine has DNA strand breakage activity and strongly inhibits IL-2 production by Jurkat cells stimulated with phytohemagglutinin (IC50 = ~1.25 mM).
• Uses: Contained in tobacco flavor additives.

Technology Process of deoxyfructosazine

There total 14 articles about deoxyfructosazine 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: 60.0%

(+)-D-glucosamine hydrochloride (1078691-95-8) → 2-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)piperazine (17460-13-8)

Guidance literature:

With boric acid; 1-ethyl-3-methylimidazolium acetate; In dimethyl sulfoxide; at 25 ℃; for 48h; Temperature;

Reference yield: 58.0%

2-deoxy-2-amino glucose (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → 2-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)piperazine (17460-13-8)

Guidance literature:

With sodium hydroxide; phenylboronic acid; at 20 ℃; for 3h;

DOI:10.1002/1099-0690(200110)2001:20<3899::aid-ejoc3899>3.0.co;2-g

Reference yield: 47.0%

(+)-D-glucosamine hydrochloride (1078691-95-8) → 2-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)piperazine (17460-13-8) + (1R,1'R,2S,2'S,3R,3'R)-1,1'-(2,5-pyrazine)-bis-1,2,3,4-butanetetraol (13185-73-4)

Guidance literature:

With ammonium hydroxide; In water; for 504h; Ambient temperature;

DOI:10.1248/cpb.39.792

upstream raw materials:

(+)-D-glucosamine hydrochloride

2-deoxy-2-amino glucose

D-glucose

D-(+)-glucosamine hydrochloride

Downstream raw materials:

1-amino-1-deoxy-D-fructose

D-erythro-3-deoxy-[2]hexosulose-bis-(4-nitro-phenylhydrazone)

Refernces

• 1、 Jia, Lingyu,Pedersen, Christian Marcus,Qiao, Yan,Deng, Tiansheng,Zuo, Pingping,Ge, Wenzhi,Qin, Zhangfeng,Hou, Xianglin,Wang, Yingxiong. "Glucosamine condensation catalyzed by 1-ethyl-3-methylimidazolium acetate: Mechanistic insight from NMR spectroscopy". . p. 23173 - 23182. Retrieved 2015.
• 2、 Eitelman,Feather. "-". . p. 205,207. Retrieved 1979.
• 3、 -. "Method for preparing 2,5-deoxyfructosazine by utilizing fructose". Paragraph 0022-0045. . Retrieved 2019/07/31.
• 4、 -. "Method for preparing deoxyfructosazine through chitin biomass". Paragraph 0031; 0032; 0033. . Retrieved 2017/01/26.