337714

Hydroquinine

98%

• Synonym(s): (8a,9R)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinine, NSC 41799
• Empirical Formula (Hill Notation): C₂₀H₂₆N₂O₂
• CAS Number: 522-66-7
• Molecular Weight: 326.43
• Beilstein/REAXYS Number: 91444
• EC Number: 208-334-0
• MDL number: MFCD00151107
• UNSPSC Code: 12352005
• PubChem Substance ID: 24860494
• NACRES: NA.22

Properties

• assay: 98%
• form: powder
• optical activity: [α]25/D −148°, c = 1 in ethanol
• mp: 168-176 °C (lit.)
• SMILES string: CC[C@H]1CN2CCC1C[C@@H]2[C@H](O)c3ccnc4ccc(OC)cc34
• InChI: 1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1
• InChI key: LJOQGZACKSYWCH-WZBLMQSHSA-N
• Gene Information: human ... CYP2D6(1565)

Description

General description

Hydroquinine is a cinchona alkaloid.

Application

Hydroquinine may be used in the preparation of its derivatives such as C9 epihydroquinine, 9-acetoxy-10,11-dihydroquinine and 10,11-dihydroquinine monohydrochloride. It may also be used as a catalyst for the methylhydrazine promoted asymmetric α-hydroxylation of β-keto esters in the presence of molecular oxygen as oxidant to form enantioenriched α-hydroxy β-dicarbonyl compounds.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H315,H317,H319,H334,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves