138622
D-(−)-Quinic acid
98%
Sinónimos:
(-)-Quinic acid, (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid, D-(-)-Quinic acid
Iniciar sesión para ver los precios por organización y contrato.
Seleccione un Tamaño
Cambiar Vistas
Acerca de este artículo
Fórmula empírica (notación de Hill):
C7H12O6
Número CAS:
Peso molecular:
192.17
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-072-8
Beilstein/REAXYS Number:
2212412
MDL number:
Servicio técnico
¿Necesita ayuda? Nuestro equipo de científicos experimentados está aquí para ayudarle.
Permítanos ayudarleQuality 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
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Elija entre una de las versiones más recientes:
¿Ya tiene este producto?
Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.
Tzenge-Lien Shih et al.
The Journal of organic chemistry, 72(11), 4258-4261 (2007-05-08)
Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an efficient manner. The key step employs dihydroxylation of protected chiral 1,4,5-cyclohex-2-enetriols under RuCl3/NaIO4/phosphate buffer (pH 7) condition
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)
d-(-)-Quinic acid: a chiron store for natural product synthesis
Barco A, et al
Tetrahedron Asymmetry, 8(21), 3515-3545 (1997)