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337714

Sigma-Aldrich

Hydroquinine

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H26N2O2
Número de CAS:
522-66-7
Peso molecular:
326.43
Beilstein/REAXYS Number:
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.)

functional group

hydroxyl

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

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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Certificados de análisis (COA)

Lot/Batch Number
0000375305
0000375305
0000396918
0000184230
0000158138

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(DHQ)2PHAL ≥95%

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
Aurélie Claraz et al.
The Journal of organic chemistry, 76(15), 6457-6463 (2011-06-18)
Herein is disclosed an efficient catalytic enantioselective protonation of enol acetates by means of a readily implementable transition-metal-free chemical process. By making use of simple hygrogenocarbonates as the proton source and hydroquinine anthraquinone-1,4-diyl diether as the chiral proton shuttle, a
Katsujiro Sato et al.
Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.], 33(8), 937-944 (2007-07-31)
Although combined use of tretinoin (all-trans-retinoic acid; atRA) and hydroquinone improves various hyperpigmented lesions, the pharmacologic instability of atRA and atRA-induced irritant dermatitis are difficult unsolved problems. The objective was to evaluate the efficacy and adverse effects of a newly
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