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96401

Sigma-Aldrich

3-Dehydroquinic acid potassium salt

≥97.0% (TLC)

Synonym(s):

(1R,3R,4S)-1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid potassium salt, 5-Dehydroquinic acid potassium salt

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About This Item

Empirical Formula (Hill Notation):
C7H9KO6
CAS Number:
494211-79-9
Molecular Weight:
228.24
MDL number:
MFCD11045271
UNSPSC Code:
12352204
PubChem Substance ID:
329770504
NACRES:
NA.32

Quality Level

100

Assay

≥97.0% (TLC)

form

powder

optical activity

[α]/D -48.0±4.0°, c = 1.5 in H2O

storage temp.

2-8°C

SMILES string

[K+].O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C([O-])=O

InChI

1S/C7H10O6.K/c8-3-1-7(13,6(11)12)2-4(9)5(3)10;/h3,5,8,10,13H,1-2H2,(H,11,12);/q;+1/p-1/t3-,5+,7-;/m1./s1

InChI key

XOXNBNMEMILWBJ-HOMRGJANSA-M

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Biochem/physiol Actions

Metabolic intermediate in the shikimate pathway; metabolite standard
Metabolite of the shikimate pathway, which is required for the synthesis of aromatic compounds in microorganismsand plants.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Osao Adachi et al.
Bioscience, biotechnology, and biochemistry, 70(12), 3081-3083 (2006-12-08)
A method for enzymatic preparation of 3-dehydroquinate and 3-dehydroshikimate in the shikimate pathway was established by controlling the enzyme activity of 3-dehydroquinate dehydratase. When quinate was incubated with the membrane fraction of acetic acid bacteria at pH 5.0, 3-dehydroquinate was
Alison Park et al.
Protein science : a publication of the Protein Society, 13(8), 2108-2119 (2004-07-27)
Dehydroquinate synthase (DHQS) is the N-terminal domain of the pentafunctional AROM protein that catalyses steps 2 to 7 in the shikimate pathway in microbial eukaryotes. DHQS converts 3-deoxy-D-arabino-heptulosonate-7-phosphate (DAHP) to dehydroquinate in a reaction that includes alcohol oxidation, phosphate beta-elimination
Wensheng Li et al.
Journal of the American Chemical Society, 127(9), 2874-2882 (2005-03-03)
The toxicity of aromatics frequently limits the yields of their microbial synthesis. For example, the 5% yield of catechol synthesized from glucose by Escherichia coli WN1/pWL1.290A under fermentor-controlled conditions reflects catechol's microbial toxicity. Use of in situ resin-based extraction to

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