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337714

Sigma-Aldrich

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
Beilstein:
91444
EC Number:
208-334-0
MDL number:
MFCD00151107
UNSPSC Code:
12352005
PubChem Substance ID:
24860494
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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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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

392723

(DHQ)2PHAL

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
Short QT syndrome in infancy. Therapeutic drug monitoring of hydroquinidine in a newborn infant.
Elisa Pirro et al.
British journal of clinical pharmacology, 72(6), 982-984 (2011-06-29)
Arghya Sadhukhan et al.
The Journal of organic chemistry, 77(16), 7076-7080 (2012-07-28)
A first approach for catalytic asymmetric Strecker reaction of aldehydes with a secondary amine in the presence of sodium fluoride using hydroquinine as chiral catalyst was developed. The catalytic system gave α-aminonitriles in excellent yields (up to 95%) and high
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