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Merck
CN

337714

Hydroquinine

98%

Synonym(s):

(8a,9R)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinine, NSC 41799

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About This Item

Empirical Formula (Hill Notation):
C20H26N2O2
CAS Number:
522-66-7
Molecular Weight:
326.43
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24860494
EC Number:
208-334-0
Beilstein/REAXYS Number:
91444
MDL number:
MFCD00151107

Key Documents

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Product Name

Hydroquinine, 98%

InChI key

LJOQGZACKSYWCH-WZBLMQSHSA-N

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

SMILES string

CC[C@H]1CN2CCC1C[C@@H]2[C@H](O)c3ccnc4ccc(OC)cc34

assay

98%

form

powder

optical activity

[α]25/D −148°, c = 1 in ethanol

mp

168-176 °C (lit.)

functional group

hydroxyl

Quality Level

200

Gene Information

human ... CYP2D6(1565)

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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.

General description

Hydroquinine is a cinchona alkaloid.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000375305
0000375305
0000396918
0000184230
0000158138

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Ion-pair formation of hydroquinine by chromatography.
Marchais S, et al.
Analytica Chimica Acta, 426(1), 85-93 (2001)
Methylhydrazine-induced enantioselective a-hydroxylation of ?-keto esters with molecular oxygen catalyzed by hydroquinine.
Wang Y, et al.
Tetrahedron, 71(1), 85-90 (2015)
Li-Ping Zhang et al.
Analytical and bioanalytical chemistry, 412(26), 7321-7332 (2020-08-14)
A novel soluble molecularly imprinted polymer (SMIP) without chemical cross-linker was successfully synthesized. The quinine (QN), which the structure was similar to the template, was chosen as the immobile template to improve the affinity of MIP. 4-Methyl phenyl dicyclohexyl ethylene
Arti T Navare et al.
Journal of mass spectrometry : JMS, 45(6), 635-642 (2010-06-09)
Atmospheric pressure (AP) matrix-assisted laser desorption/ionization (MALDI) is known to suffer from poor ion transfer efficiencies as compared to conventional vacuum MALDI (vMALDI). To mitigate these issues, a new AP-MALDI ion source utilizing a coaxial gas flow was developed. Nitrogen
Ad Kane et al.
Annales de cardiologie et d'angeiologie, 61(4), 292-295 (2011-06-15)
A 45-year-old man was hospitalized for syncope due to fascicular ventricular tachycardia degenerating into ventricular fibrillation (VF). The electrocardiogram showed an early repolarization syndrome. The arrhythmia was repetitive and disappeared after oral hydroquinidine. An implantable cardioverter-defibrillator (ICD) was implanted; subsequently
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