4-Deoxypyridoxine
Appearance
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Preferred IUPAC name
5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H11NO2 | |
Molar mass | 153.181 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Deoxypyridoxine is a vitamin B6 antagonist.[1] It may be toxic to developing embryos since it can have negative effects on collagen and elastin during development.[2] The presence of this compound can produce vitamin B6 deficiency, which suppresses the immune system.[3] This immunosuppression can be beneficial in animal models of Trichinella spiralis infections.[4] 4-Deoxypyridoxine has also been described as an inhibitor of sphingosine-1-phosphate lyase.[5]
References
- ^ Coburn SP, Mahuren JD, Schaltenbrand WE, Wostmann BS, Madsen D (1 February 1981). "Effects of vitamin B-6 deficiency and 4'- deoxypyridoxine on pyridoxal phosphate concentrations, pyridoxine kinase and other aspects of metabolism in the rat". J. Nutr. 111 (2): 391–8. doi:10.1093/jn/111.2.391. PMID 6257871.
- ^ Bird TA, Levene CI (1983). "The effect of a vitamin B-6 antagonist, 4-deoxypyridoxine, on the cross-linking of collagen in the developing chick embryo". Biochem. J. 210 (3): 633–8. doi:10.1042/bj2100633. PMC 1154271. PMID 6135414.
- ^ Trakatellis A, Dimitriadou A, Exindari M, et al. (1992). "Effect of pyridoxine deficiency on immunological phenomena". Postgrad Med J. 68 Suppl 1: S70–7. PMID 1409221.
- ^ Frydas S, Papaioanou N, Vlemmas I, et al. (1999). "Vitamin B6-deficient diet plus 4-deoxypyridoxine (4-DPD) reduces the inflammatory response induced by T. spiralis in diaphragm, masseter and heart muscle tissue of mice". Mol. Cell. Biochem. 197 (1–2): 79–85. doi:10.1023/A:1006958310081. PMID 10485327. S2CID 23457740.
- ^ Weigel, Cynthia; Hüttner, Sören S.; Ludwig, Kristin; Krieg, Nadine; Hofmann, Susann; Schröder, Nathalie H.; Robbe, Linda; Kluge, Stefan; Nierhaus, Axel; Winkler, Martin S.; Rubio, Ignacio (2020-08-01). "S1P lyase inhibition protects against sepsis by promoting disease tolerance via the S1P/S1PR3 axis". EBioMedicine. 58: 102898. doi:10.1016/j.ebiom.2020.102898. ISSN 2352-3964. PMC 7381498. PMID 32711251.
External links
- Media related to 4-Deoxypyridoxine at Wikimedia Commons