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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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Methylhydrazine-induced enantioselective a-hydroxylation of ?-keto esters with molecular oxygen catalyzed by hydroquinine.
Wang Y, et al.
Tetrahedron, 71(1), 85-90 (2015)
Ion-pair formation of hydroquinine by chromatography.
Marchais S, et al.
Analytica Chimica Acta, 426(1), 85-93 (2001)
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
Xiaoyi Wei et al.
Talanta, 77(3), 1197-1202 (2008-12-10)
An on-line solid-phase extraction (SPE)-HPLC method was developed for simultaneous screening of nicardipine and amlodipine in human plasma. A short monolithic poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) [p(GMA-EDMA)]-based weak cation-exchange (WCX) column was prepared and employed as the selective extraction sorbent, which
Pankaj Kumar Arora et al.
PloS one, 7(6), e38676-e38676 (2012-06-16)
A 2-chloro-4-nitrophenol (2C4NP) degrading bacterial strain designated as RKJ 800 was isolated from a pesticide contaminated site of India by enrichment method and utilized 2C4NP as sole source of carbon and energy. The stoichiometric amounts of nitrite and chloride ions
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