Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

05616

Sigma-Aldrich

3-Dehydroshikimic acid

≥95.0% (HPLC)

Synonym(s):

(4S,5R)-(−)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid, 3-DHS, 5-Dehydroshikimic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C7H8O5
CAS Number:
2922-42-1
Molecular Weight:
172.14
MDL number:
MFCD00216518
UNSPSC Code:
12352106
PubChem Substance ID:
329748115
NACRES:
NA.25

Assay

≥95.0% (HPLC)

form

powder

optical activity

[α]/D -59.0±3.0°, c = 1 in ethanol

color

white to off-white

storage temp.

2-8°C

SMILES string

O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O

InChI

1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1

InChI key

SLWWJZMPHJJOPH-PHDIDXHHSA-N

Looking for similar products? Visit Product Comparison Guide

Application

3-Dehydroshikimic acid is a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid. 3-Dehydroshikimic acid has been used in a study to describe the synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester. 3-Dehydroshikimic acid has also been used in studies to evaluate the shikimate biosynthetic pathway, in order to develop nontoxic antimicrobial agents, herbicides, and antiparasite drugs.

Biochem/physiol Actions

Metabolite of the shikimate pathway with a chromophore suitable for continuous spectrophotometric assay. Precursor of aromatic metabolites in microorganisms.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jianhua Gan et al.
Biochemistry, 46(33), 9513-9522 (2007-07-26)
The shikimate biosynthetic pathway is essential to microorganisms, plants, and parasites but absent from mammals. Therefore, shikimate dehydrogenase (SD) and other enzymes in the pathway are attractive targets for developing nontoxic antimicrobial agents, herbicides, and antiparasite drugs. SD catalyzes the
Verónica F V Prazeres et al.
Journal of medicinal chemistry, 53(1), 191-200 (2009-11-17)
The shikimic acid pathway is essential to many pathogens but absent in mammals. Enzymes in its pathway are therefore appropriate targets for the development of novel antibiotics. Dehydroquinase is the third enzyme of the pathway, catalyzing the reversible dehydratation of
Namdeo N Bhujbal et al.
Carbohydrate research, 344(6), 734-738 (2009-03-10)
Synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived beta-ketoester is described. The polyhydroxylated beta-ketoester obtained from the hydrolysis of sugar beta-ketoester 3 was subjected to an aldol-type condensation to get 4 that on enolization, dehydration, and hydrogenation

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service