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Merck

138622

Sigma-Aldrich

D-(−)-奎宁酸

98%

别名:

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

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About This Item

经验公式(希尔记法):
C7H12O6
CAS号:
分子量:
192.17
Beilstein:
2212412
EC號碼:
MDL號碼:
分類程式碼代碼:
51113400
PubChem物質ID:
NACRES:
NA.22

化驗

98%

形狀

powder

光學活性

[α]20/D −43.9°, c = 11.2 in H2O

SMILES 字串

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 密鑰

AAWZDTNXLSGCEK-WYWMIBKRSA-N

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一般說明

D -(-)-奎尼酸是一种植物代谢产物,是多步化学合成天然产物的手性结构单元。

應用

D -(-)-奎尼酸已被用作标准品,通过 HPLC 测定苦龙胆茶 和开发蔓越莓果实中有机酸的组成。可用于制备 3,4- O -异亚丙基-3 ( R ),4 ( S )-二羟基环己酮。
D-(−)-奎宁酸可:      
  • 与硫酸铜(II)一起用作手性选择电解质。该电解质用于通过配体交换毛细管电泳法对DL酒石酸进行手性拆分。        
  • 合成3,4,6-三羟基氮杂卓、7-羟甲基-3,4,5-三羟基氮杂卓和3,4,5-三羟基氮杂卓的立体异构体的起始物质,作为糖苷酶的潜在抑制剂。        
  • 用于制备三羟基哌啶衍生物和(+)-原栎醇糖苷酶抑制剂的前体。

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

Eye Irrit. 2

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 1

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

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)
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 facile synthesis of a new trihydroxy piperidine derivative and (+)-proto-quercitol from d-(-)-quinic acid
Shih T-L, et al.
Tetrahedron Letters, 45(29), 5751-5754 (2004)
S Kodama et al.
Journal of chromatography. A, 932(1-2), 139-143 (2001-11-07)
Chiral resolution of native DL-tartaric acid was performed by ligand-exchange capillary electrophoresis using copper(II)-D-quinic acid as a chiral selector. Factors affecting chiral resolution, migration time, and peak area of tartaric acid were studied. The running conditions for optimum separation of

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