138622

D-(−)-Quinic acid

98%

• Synonym(s): (-)-Quinic acid, (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid, D-(-)-Quinic acid
• Empirical Formula (Hill Notation): C₇H₁₂O₆
• CAS Number: 77-95-2
• Molecular Weight: 192.17
• Beilstein: 2212412
• EC Number: 201-072-8
• MDL number: MFCD00003864
• UNSPSC Code: 51113400
• PubChem Substance ID: 24848361
• NACRES: NA.22

Properties

• Assay: 98%
• form: powder
• optical activity: [α]20/D −43.9°, c = 11.2 in H₂O
• functional group: carboxylic acid; hydroxyl
• SMILES string: O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
• InChI: 1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
• InChI key: AAWZDTNXLSGCEK-WYWMIBKRSA-N

Description

General description

D-(-)-Quinic acid, a plant metabolite, is chiral building block used in multistep chemical synthesis of natural compounds.

Application

D-(−)-Quinic acid can be used as:      

• A chiral selector electrolyte along with copper(II) sulfate. This electrolyte is utilized in chiral resolution DL-tartaric acid by ligand-exchange capillary electrophoresis method.        
• A starting material in the synthesis of stereoisomers of 3,4,6-trihydroxyazepanes, 7-hydroxymethyl-3,4,5-trihydroxyazepanes, and 3,4,5-trihydroxyazepanes, as potential inhibitors of glycosidase.        
• A precursor for the preparation of trihydroxy piperidine derivatives and (+)-proto-quercitol glycosidase inhibitors.

D-(-)-Quinic acid has been used as a standard to determine the composition of organic acids in bitter gentian teas and in developing cranberry fruit by HPLC. It may be used in the preparation of 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319
• Precautionary Statements: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves