138622
D-(−)-Quinic acid
98%
Synonym(s):
(-)-Quinic acid, (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid, D-(-)-Quinic acid
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About This Item
Empirical Formula (Hill Notation):
C7H12O6
CAS Number:
Molecular Weight:
192.17
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-072-8
Beilstein/REAXYS Number:
2212412
MDL number:
Quality Level
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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d-(-)-Quinic acid: a chiron store for natural product synthesis
Barco A, et al
Tetrahedron Asymmetry, 8(21), 3515-3545 (1997)
A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo [2.2. 1] heptane ring systems from D (-)-quinic acid: Application to the formal synthesis of (-)-balanol and (-)-epibatidine
Albertini E, et al
Tetrahedron Letters, 38(4), 681-684 (1997)
Xiao Liu et al.
Molecular cell, 67(2), 203-213 (2017-06-27)
Although the coupling between circadian and cell cycles allows circadian clocks to gate cell division and DNA replication in many organisms, circadian clocks were thought to function independently of cell cycle. Here, we show that DNA replication is required for