130536-38-8

Basic information

• Product Name: (+-)-trans-5,6-Dihydroxy-5,6-dihydroquinoline
• Synonyms: (+-)-trans-5,6-Dihydroxy-5,6-dihydroquinoline
• CAS NO: 130536-38-8
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 0
• Mol File: 130536-38-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Refractive Index: 1.675
• CAS DataBase Reference: (+-)-trans-5,6-Dihydroxy-5,6-dihydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (+-)-trans-5,6-Dihydroxy-5,6-dihydroquinoline(130536-38-8)
• EPA Substance Registry System: (+-)-trans-5,6-Dihydroxy-5,6-dihydroquinoline(130536-38-8)

Safety Data

• Hazardous Substances Data: 130536-38-8(Hazardous Substances Data)

Usage

General Description

(+)-trans-5,6-Dihydroxy-5,6-dihydroquinoline, also known as cinchonine, is a natural product found in cinchona bark. It is a stereoisomer of quinine, and has similar pharmacological properties, including antimalarial and analgesic effects. Cinchonine has been studied for its potential use in the treatment of malaria, as well as its ability to inhibit the growth of cancer cells. It also has been found to have anti-inflammatory and antiviral properties. The compound is commonly used in the synthesis of pharmaceuticals and as a chiral resolving agent in the production of enantiopure compounds.

InChI:InChI=1/C9H9NO2/c11-8-4-3-7-6(9(8)12)2-1-5-10-7/h1-5,8-9,11-12H/t8-,9-/m1/s1

Upstream product

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

Relevant articles and documents

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.