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138622

Sigma-Aldrich

D-(−)-Quinic acid

98%

Sinonimo/i:

(-)-Quinic acid, (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid, D-(-)-Quinic acid

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About This Item

Formula empirica (notazione di Hill):
C7H12O6
Numero CAS:
77-95-2
Peso molecolare:
192.17
Beilstein:
2212412
Numero CE:
201-072-8
Numero MDL:
MFCD00003864
Codice UNSPSC:
51113400
ID PubChem:
24848361
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Forma fisica

powder

Attività ottica

[α]20/D −43.9°, c = 11.2 in H2O

Stringa SMILE

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
AAWZDTNXLSGCEK-WYWMIBKRSA-N

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Descrizione generale

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

Applicazioni

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H319

Classi di pericolo

Eye Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG1838
BCCD5637
BCCC9683
BCCB3950
BCBW9003

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Christopher J Potter et al.
Nature protocols, 6(8), 1105-1120 (2011-07-09)
In Drosophila, the GAL4/UAS/GAL80 repressible binary expression system is widely used to manipulate or mark tissues of interest. However, complex biological systems often require distinct transgenic manipulations of different cell populations. For this purpose, we recently developed the Q system
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)
Qiuling Li et al.
G3 (Bethesda, Md.), 6(10), 3351-3359 (2016-08-26)
Drosophila melanogaster is a powerful model organism for dissecting the molecular mechanisms that regulate sleep, and numerous studies in the fly have identified genes that impact sleep-wake cycles. Conditional genetic analysis is essential to distinguish the mechanisms by which these
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