MedKoo Cat#: 145037 | Name: Fructosazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fructosazine is a polyhydroxyalkylpyrazine reported to have antimicrobial activity against heat-resistant Escherichia coli AW 1.7. Fructosazine exerts antimicrobial action by permeabilizing the cell membrane, damaging membrane integrity, and fragmenting DNA. Fructosazine is also a flavoring agent in the food and tobacco industry.

Chemical Structure

Fructosazine
Fructosazine
CAS#13185-73-4

Theoretical Analysis

MedKoo Cat#: 145037

Name: Fructosazine

CAS#: 13185-73-4

Chemical Formula: C12H20N2O8

Exact Mass: 320.1220

Molecular Weight: 320.30

Elemental Analysis: C, 45.00; H, 6.29; N, 8.75; O, 39.96

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Fructosazine;
IUPAC/Chemical Name
(1R,1'R,2S,2'S,3R,3'R)-1,1'-(pyrazine-2,5-diyl)bis(butane-1,2,3,4-tetraol)
InChi Key
NPWQIVOYGNUVEB-PAUJSFGCSA-N
InChi Code
1S/C12H20N2O8/c15-3-7(17)11(21)9(19)5-1-13-6(2-14-5)10(20)12(22)8(18)4-16/h1-2,7-12,15-22H,3-4H2/t7-,8-,9-,10-,11-,12-/m1/s1
SMILES Code
OC[C@@H](O)[C@@H](O)[C@H](O)C1=CN=C(C=N1)[C@@H](O)[C@H](O)[C@H](O)CO
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 320.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bhattacherjee A, Hrynets Y, Betti M. Fructosazine, a Polyhydroxyalkylpyrazine with Antimicrobial Activity: Mechanism of Inhibition against Extremely Heat Resistant Escherichia coli. J Agric Food Chem. 2016 Nov 16;64(45):8530-8539. doi: 10.1021/acs.jafc.6b03755. Epub 2016 Nov 2. PMID: 27776403. 2: Bhattacherjee A, Hrynets Y, Betti M. Transport of the Glucosamine-Derived Browning Product Fructosazine (Polyhydroxyalkylpyrazine) Across the Human Intestinal Caco-2 Cell Monolayer: Role of the Hexose Transporters. J Agric Food Chem. 2017 Jun 14;65(23):4642-4650. doi: 10.1021/acs.jafc.7b01611. Epub 2017 Jun 1. PMID: 28535336. 3: Bhattacherjee A, Hrynets Y, Betti M. Improved bactericidal capacity of UV-B radiation against E. coli strains by photosensitizing bacteria with fructosazine - An advanced Maillard reaction product. Food Chem. 2019 Jan 15;271:354-361. doi: 10.1016/j.foodchem.2018.07.191. Epub 2018 Jul 26. PMID: 30236687. 4: Henry N, Delépée R, Seigneuret JM, Agrofoglio LA. Synthesis of water- compatible imprinted polymers of in situ produced fructosazine and 2,5-deoxyfructosazine. Talanta. 2012 Sep 15;99:816-23. doi: 10.1016/j.talanta.2012.07.035. Epub 2012 Jul 22. PMID: 22967628. 5: Zhao M, Araújo MM, Dal S, Sigrist S, Bergaentzlé M, Ramanitrahasimbola D, Andrianjara C, Marchioni E. Development and validation of a selective and effective pressurized liquid extraction followed by liquid chromatography-mass spectrometry method for the determination of fructosazine analogues in the ammonia treated extract of Eugenia jambolana Lamarck seeds. J Chromatogr A. 2016 Nov 18;1473:66-75. doi: 10.1016/j.chroma.2016.10.035. Epub 2016 Oct 13. PMID: 27771103. 6: Dhungel P, Hrynets Y, Betti M. Sous-Vide Nonenzymatic Browning of Glucosamine at Different Temperatures. J Agric Food Chem. 2018 May 2;66(17):4521-4530. doi: 10.1021/acs.jafc.8b01265. Epub 2018 Apr 23. PMID: 29658276. 7: Hrynets Y, Bhattacherjee A, Ndagijimana M, Hincapie Martinez DJ, Betti M. Iron (Fe(2+))-Catalyzed Glucosamine Browning at 50 °C: Identification and Quantification of Major Flavor Compounds for Antibacterial Activity. J Agric Food Chem. 2016 Apr 27;64(16):3266-75. doi: 10.1021/acs.jafc.6b00761. Epub 2016 Apr 11. PMID: 27043007. 8: Kashige N, Yamaguchi T, Mishiro N, Hanazono H, Miake F, Watanabe K. Possible involvement of dihydrofructosazine in the DNA breaking activity of D-glucosamine. Biol Pharm Bull. 1995 May;18(5):653-8. doi: 10.1248/bpb.18.653. PMID: 7492977. 9: Zhao X, Hrynets Y, Betti M. Cold non-enzymatic browning of glucosamine in the presence of metmyoglobin induces glucosone and deoxymyoglobin formation. Food Chem. 2020 Feb 1;305:125504. doi: 10.1016/j.foodchem.2019.125504. Epub 2019 Sep 10. PMID: 31606691. 10: Dhungel P, Bhattacherjee A, Hrynets Y, Betti M. The effect of amino acids on non-enzymatic browning of glucosamine: Generation of butterscotch aromatic and bioactive health compounds without detectable levels of neo-formed alkylimidazoles. Food Chem. 2020 Mar 5;308:125612. doi: 10.1016/j.foodchem.2019.125612. Epub 2019 Oct 4. PMID: 31670192. 11: Jia L, Pedersen CM, Qiao Y, Deng T, Zuo P, Ge W, Qin Z, Hou X, Wang Y. Glucosamine condensation catalyzed by 1-ethyl-3-methylimidazolium acetate: mechanistic insight from NMR spectroscopy. Phys Chem Chem Phys. 2015 Sep 21;17(35):23173-82. doi: 10.1039/c5cp02169c. PMID: 26278065. 12: Liu P, Zhang J, Qiao Y, Hou X, Liu Y, Wang Y. Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy. J Agric Food Chem. 2021 Mar 3;69(8):2403-2411. doi: 10.1021/acs.jafc.0c08032. Epub 2021 Feb 17. PMID: 33595305. 13: Sumoto K, Irie M, Mibu N, Miyano S, Nakashima Y, Watanabe K, Yamaguchi T. Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid (DNA) strand breakage activity. Chem Pharm Bull (Tokyo). 1991 Mar;39(3):792-4. doi: 10.1248/cpb.39.792. PMID: 2070466. 14: Jun M, Shao Y, Ho CT, Koetter U, Lech S. Structural identification of nonvolatile dimerization products of glucosamine by gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance analysis. J Agric Food Chem. 2003 Oct 8;51(21):6340-6. doi: 10.1021/jf034587n. PMID: 14518965. 15: Nashalian O, Yaylayan VA. In situ formation of the amino sugars 1-amino-1-deoxy-fructose and 2-amino-2-deoxy-glucose under Maillard reaction conditions in the absence of ammonia. Food Chem. 2016 Apr 15;197(Pt A):489-95. doi: 10.1016/j.foodchem.2015.10.140. Epub 2015 Oct 30. PMID: 26616979. 16: Zhu A, Huang JB, Clark A, Romero R, Petty HR. 2,5-Deoxyfructosazine, a D-glucosamine derivative, inhibits T-cell interleukin-2 production better than D-glucosamine. Carbohydr Res. 2007 Dec 28;342(18):2745-9. doi: 10.1016/j.carres.2007.08.025. Epub 2007 Sep 7. PMID: 17892867; PMCID: PMC2758268. 17: Hrynets Y, Ndagijimana M, Betti M. Studies on the Formation of Maillard and Caramelization Products from Glucosamine Incubated at 37 °C. J Agric Food Chem. 2015 Jul 15;63(27):6249-61. doi: 10.1021/acs.jafc.5b02664. Epub 2015 Jul 2. PMID: 26114422. 18: Shimamura T, Takamori A, Ukeda H, Sawamura M. Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative. Biosci Biotechnol Biochem. 2003 Feb;67(2):295-9. doi: 10.1271/bbb.67.295. PMID: 12728989. 19: Candiano G, Ghiggeri GM, Gusmano R, Zetta L, Benfenati E, Icardi G. Reaction of 2-amino-2-deoxy-D-glucose and lysine: isolation and characterization of 2,5-bis(tetrahydroxybutyl)pyrazine. Carbohydr Res. 1988 Dec 31;184:67-75. doi: 10.1016/0008-6215(88)80006-5. PMID: 3149546.