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.
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IUPAC name
(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
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Other names
(8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
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3D model (JSmol)
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ECHA InfoCard | 100.007.578 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C20H26N2O2 | |
Molar mass | 326.440 g·mol−1 |
Melting point | 173–175 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]