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Hydroxy pentoxifylline

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Hydroxy pentoxifylline manufacturers

  • (±)-Lisofylline
  • (±)-Lisofylline pictures
  • $33.00
  • 2026-07-27
  • CAS:6493-06-7
  • Purity: 99.91%
  • Supply Ability: 10g
Hydroxy pentoxifylline Basic information
Synthesis
Product Name:Hydroxy pentoxifylline
Synonyms:(+/-)-LISOFYLLINE;pentoxyfylline metabolite 2;(+/-)-1-(5-HYDROXYHEXYL)-3,7-DIMETHYLXANTHINE;1-(5-Hydroxyhexyl)-3,7-dimethyl-1,2,3,6-tetrahydro-7H-purine-2,6-dione;Penthydroxifillyne;3,7-Dihydro-1-(5-hydroxyhexyl)-3,7-diMethyl-;5-Hydroxy pentoxifylline;Hydroxy Pentoxifylline (rac-Lisofylline)
CAS:6493-06-7
MF:C13H20N4O3
MW:280.32
EINECS:
Product Categories:Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
Mol File:6493-06-7.mol
Hydroxy pentoxifylline Structure
Hydroxy pentoxifylline Chemical Properties
Melting point 123-125°C
Boiling point 511.2±56.0 °C(Predicted)
density 1.32±0.1 g/cm3(Predicted)
storage temp. Refrigerator
solubility DMSO: soluble
form solid
pka15.22±0.20(Predicted)
color white
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
InChIInChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3
InChIKeyNSMXQKNUPPXBRG-UHFFFAOYSA-N
SMILESN1(C)C2=C(N(C)C(=O)N(CCCCC(O)C)C2=O)N=C1
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
Hydroxy pentoxifylline Usage And Synthesis
SynthesisIn an anhydrous and oxygen-free glove box, cobalt complex (0.005–0.04 mmol, 0.5–4 mol%) or an in-situ cobalt carbene catalytic system [i.e., a mixture of CoCl2 (0.005–0.04 mmol, 0.5–4 mol%) and a 3-aza-heterocyclic carbene ligand (0.005–0.04 mmol, 0.5–4 mol%)] and an appropriate amount of base (0.05–0.2 mmol, 5–20 mol%) were added to a 4 mL glass reaction flask containing a magnetic stir bar, followed by 0.5 mL of solvent, and finally the substrate (1 mmol). After shaking for 30 seconds, the mixture was transferred to a ParrInstruments high-pressure reactor. After removing the high-pressure reactor from the glove box, hydrogen gas at 10–30 bar was introduced, and the reaction temperature was set at 25–60 °C for 16 hours. After the reaction was stopped, the high-pressure reactor was first cooled in a 0 °C ice-water bath, and then the hydrogen gas inside the reactor was slowly released. The reaction flask was removed from the high-pressure reactor, and the product HYDROXY PENTOXIFYLLINE was separated by rapid column chromatography and weighed to obtain the yield.
DescriptionLisofylline (6493-06-7, racemic) displays anti-inflammatory activity. Regulates immune cell function and autoimmune response by inhibition of IL-12 signalling and cytokine production.1 Protects pancreatic beta cells and prevents type I diabetes in non-obese diabetic mice.2 Lisofylline reduces LPS-induced TNF alpha levels in CD-1 mice.3Cell permeable.
Chemical PropertiesWhite Solid
UsesA major oxidative metabolite of Pentoxifylline. A potent inhibitor of phosphatidic acid generation (IC50=0.6uM). Protects mice from endotoxic shock and attenuates sepsis-induced acute lung injury in pig.
DefinitionChEBI: 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione is a dimethylxanthine that is 3,7-dihydro-1H-purine-2,6-dione which is substituted at positions 1,3 and 7 by a 5-hydroxyhexyl group, methyl group and methyl group, respectively. It is a secondary alcohol and a dimethylxanthine.
Brand nameProTec (Cell Therapeutics).
in vitro(±)-lisofylline is a potent anti-inflammatory agent in which only the (-) optical isomer is biologically active. (±)-lisofylline was found to inhibit the generation of phosphatidic acid from cytokine-activated lysophosphatidic acyl transferase. (±)-lisofylline could also suppress the production of the proinflammatory cytokine ifn-γ, inhibit il-12-mediated stat-4 activation, as well as enhance glucose-stimulated β-cell insulin secretion [1].
in vivoin a previous study, lisofylline was administered to female non-obese diabetic mice for 3 weeks. cytokines and blood glucose concentrations were monitored. histology and immunohistochemistry were also carried out in pancreatic sections. results showed that lisofylline was able to suppress ifn-γ production, reduce the onset of insulitis and diabetes, and inhibit diabetes [1].
References[1] ZANDONG YANG  Jerry L N  Meng Chen. Lisofylline: a potential lead for the treatment of diabetes[J]. Biochemical pharmacology, 2005, 69 1: Pages 1-5. DOI:10.1016/j.bcp.2004.08.012
[2] Z-D YANG. The anti-inflammatory compound lisofylline prevents Type I diabetes in non-obese diabetic mice.[J]. Diabetologia, 2002, 45 9: 1307-1314. DOI:10.1007/s00125-002-0901-y
[3] WYSKA E. Pharmacokinetic-pharmacodynamic modeling of methylxanthine derivatives in mice challenged with high-dose lipopolysaccharide.[J]. Pharmacology, 2010, 85 5: 264-271. DOI:10.1159/000288734
Hydroxy pentoxifylline Preparation Products And Raw materials
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