Dihydroquinine

Dihydroquinine, also known as hydroquinine^[1] or DHQ, is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is −148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

Quick facts Names, Identifiers ...

Dihydroquinine

Names
IUPAC name (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names (8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS Number	522-66-7 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:135994
ChEMBL	ChEMBL588934
ChemSpider	108426 Y
DrugBank	DB13718
ECHA InfoCard	100.007.578
EC Number	208-334-0
PubChem CID	121515
UNII	31J3Q51T6L Y
CompTox Dashboard (EPA)	DTXSID70878516
InChI 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 Y Key: LJOQGZACKSYWCH-WZBLMQSHSA-N Y InChI=1/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 Key: LJOQGZACKSYWCH-WZBLMQSHBC
SMILES O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43 O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C
Properties
Chemical formula	C20H26N2O2
Molar mass	326.440 g·mol−1
Melting point	173–175 °C
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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DHQ also inhibits growth of the parasite Toxoplasma gondii by inducing mitochondrial membrane damage, but does not disrupt host mitochondrial membrane potential, as well as reactive oxygen species (ROS) generation.^[2]