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138622

Sigma-Aldrich

D-(−)-Quinic acid

98%

Empirical Formula (Hill Notation):
C7H12O6
CAS Number:
Molecular Weight:
192.17
Beilstein:
2212412
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

powder

optical activity

[α]20/D −43.9°, c = 11.2 in H2O

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

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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.

Packaging

25, 100 g in poly bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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