A pyrazine derivative
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Product Type

Biochemicals
Natural Products

Research Area

Immunology & Inflammation

2,5-Deoxyfructosazine (hydrochloride)

Item No. 18662

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2S,3R) 1-[5-[(2S,3R)-2,3,4-trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol, dihydrochloride
CAS Number
17460-13-8
Synonyms
  • NSC 270912
Molecular Formula
C12H20N2O7 • 2HCl
Formula Weight
377.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 3 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
274 nm
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)C1=CN=C(C[C@H](O)[C@H](O)CO)C=N1.Cl.Cl
InChi Code
InChI=1S/C12H20N2O7.2ClH/c15-4-9(18)8(17)1-6-2-14-7(3-13-6)11(20)12(21)10(19)5-16;;/h2-3,8-12,15-21H,1,4-5H2;2*1H/t8-,9+,10+,11+,12+;;/m0../s1
InChi Key
FNUXEFPZXSEEBI-DIEPXXOHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $152

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    5 mg

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    Product 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.1,2 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 2,5-Deoxyfructosazine is also formed by the breakdown of D-glucosamine at neutral pH.3,4 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).5,4,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Henry, N., Delépée, R., Seigneuret, J.M., et al. Synthesis of water-compatible imprinted polymers of in situ produced fructosazine and 2,5-deoxyfructosazine. Talanta 99, 816-823 (2012).

    2. Rodgman, A., and Perfetti, T.A. The chemical components of tobacco and tobacco smoke, Second Edition. Second, (2013).

    3. Zhu, A., Huang, J.B., Clark, A., et al. 2,5-Deoxyfructosazine, a D-glucosamine derivative, inhibits T-cell interleukin-2 production better than D-glucosamine. Carbohydr. Res. 342(18), 2745-2749 (2007).

    4. Shimamura, T., Takamori, A., Ukeda, H., et al. Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative. Biosci. Biotechnol. Biochem. 67(2), 295-299 (2003).

    5. Sumoto, K., Irie, M., Mibu, N., et al. Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid (DNA) strand breakage activity. Chem. Pharm. Bull. (Tokyo) 39(3), 792-794 (1991).