138622
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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关于此项目
经验公式（希尔记法）:
C7H12O6
化学文摘社编号:
分子量:
192.17
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-072-8
Beilstein/REAXYS Number:
2212412
MDL number:
产品名称
D-(−)-奎宁酸, 98%
InChI key
AAWZDTNXLSGCEK-WYWMIBKRSA-N
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
SMILES string
O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
assay
98%
form
powder
optical activity
[α]20/D −43.9°, c = 11.2 in H2O
functional group
carboxylic acid
hydroxyl
Quality Level
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Application
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。
General description
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。
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
存储类别
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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)
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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