112259-26-4

Basic information

• Product Name: (5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline
• Synonyms: (5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline
• CAS NO: 112259-26-4
• Molecular Weight: 163.176
• Mol File: 112259-26-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline(112259-26-4)
• EPA Substance Registry System: (5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline(112259-26-4)

Safety Data

• Hazardous Substances Data: 112259-26-4(Hazardous Substances Data)

Upstream product

• 91-22-5 quinoline 
• 87707-14-0 1a,7b-dihydrooxireno[2,3-f]quinoline 

Downstream Products

• 135096-28-5 (1aS,7bR)-1a,7b-Dihydro-1-oxa-4-aza-cyclopropa[a]naphthalene 
• 158060-56-1 (1aS,7bR)-1a,2,3,7b-Tetrahydro-1-oxa-4-aza-cyclopropa[a]naphthalene 

Relevant articles and documents

Metabolites of quinoline, a hepatocarcinogen in a subcellular microsomal system

It was evidenced that quinoline was metabolized to quinoline 1-oxide catalyzed by cytochrome P-450-linked mixed function monooxygenase system and to 5,6-trans-dihydroxy-5,6-dihydroquinoline by cytochrome P-448-linked one. The third metabolite, 3-hydroxyquinoline, may be produced in another course of metabolism, which might be connected with genotoxicity of quinoline, as previously discussed.

Solvolysis of the Quinoline 5,6- and 7,8-Oxides: Effect of the Ring Nitrogen

pH-rate profiles for the hydrolysis of quinoline arene oxides were measured in 1:9 dioxane-water at 25 deg C (0.1 M NaClO4) and compared with the parent carbocylic compound naphthalene 1,2-oxide.Unlike naphthalene 1,2-oxide whose hydrolysis rate shows a first-order dependence on hydronium ion concentration (kH) below pH 5, rates for the quinoline 5,6- and 7,8-oxides show a kH reaction (0.14 and 1.54 M-1 s-1 for quinoline 5,6- and 7,8-oxides, respectively), but plateau below pH 2-3. pH-independent rate constants in the low-pH plateau are 2.7E-5 and 1.7E-3 s-1for the 5,6- and 7,8-oxides, respectively.On the basis of studies of the N-methyl cation of the 5,6-oxide (kobsd -1 at pH 1.8), it is concluded that the low-pH plateau is due to lack of reactivity for the N-protonated quinoline oxides.Also unlike naphthalene oxide, the quinoline oxides show a reaction with hydroxide ion (kOH rate) that results in the formation of trans dihydrodiols.In acid, quinoline 5,6-oxide, but not quinoline 7,8-oxide, gives a significant yield (20percent) of the trans dihydrodiol product and provides the first example of a benzo-ring arene oxide that forms dihydrodiol product under acidic conditions.Other products of the acid-catalyzed reaction of the 5,6-oxide are 5- (73percent) and 6- (7percent) hydroxyquinolines.The 7,8-oxide upon solvolysis in acid gave exclusively 8-hydroxyquinoline.The 100-1000 fold decrease in reactivity of the quinoline oxides, relative to naphthalene oxide in the pH range of 1-10, can be accounted for in terms of the presence of their ring nitrogens and the differences in the pKa values of these nitrogens.