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hydroquinine
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Dihydroquinine, also known as hydroquinine 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.
Chemical data
- Formula
- C20H26N2O2
- Molecular weight
- 326.4 g/mol
- IUPAC name
- (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 326.199
Show 4 more facts
- chemical formula
- C₂₀H₂₆N₂O₂
- canonical SMILES
- CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
- isomeric SMILES
- CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)O
- Commons category
- Dihydroquinine
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Dihydroquinine, also known as hydroquinine 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.
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.
Excerpted from Wikipedia’s “hydroquinine” article, available under the CC BY-SA 4.0 licence.