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337714

Sigma-Aldrich

Hydroquinine

98%

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Synonym(s):
(8a,9R)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinine, NSC 41799
Empirical Formula (Hill Notation):
C20H26N2O2
CAS Number:
Molecular Weight:
326.43
Beilstein/REAXYS Number:
91444
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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)

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1 of 4

This Item
35934325481922630
Hydroquinine 98%

337714

Hydroquinine

Hydroquinidine 95%

359343

Hydroquinidine

Hydroquinidine hydrochloride 98%

254819

Hydroquinidine hydrochloride

Quinine hydrochloride dihydrate BioReagent, suitable for fluorescence, ≥98.0% (NT)

22630

Quinine hydrochloride dihydrate

form

powder

form

-

form

powder

form

powder

mp

168-176 °C (lit.)

mp

169-170 °C (lit.)

mp

277-279 °C (lit.)

mp

-

optical activity

[α]25/D −148°, c = 1 in ethanol

optical activity

[α]25/D +226°, c = 2 in ethanol

optical activity

[α]20/D +185.2°, c = 1.3 in H2O

optical activity

[α]20/D −230±5°, c = 2% in 0.1 M HCl

Gene Information

human ... CYP2D6(1565)

Gene Information

human ... CYP2D6(1565)

Gene Information

-

Gene Information

-

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.

pictograms

Exclamation markHealth hazard

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
Saleem Aladaileh et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 148(4), 470-480 (2007-10-24)
Phenoloxidase (PO) activity was studied in Sydney rock oysters (Saccostrea glomerata). As in other molluscs, PO was found to exist as a pro-enzyme (proPO) in hemocytes. ProPO could be activated to PO by exogenous proteases (trypsin and chymotrypsin), exposure of

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