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05616

Sigma-Aldrich

3-Dehydroshikimic acid

≥95.0% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C7H8O5
Numero CAS:
2922-42-1
Peso molecolare:
172.14
Numero MDL:
MFCD00216518
Codice UNSPSC:
12352106
ID PubChem:
329748115
NACRES:
NA.25

Livello qualitativo

100

Saggio

≥95.0% (HPLC)

Stato

powder

Attività ottica

[α]/D -59.0±3.0°, c = 1 in ethanol

Colore

white to off-white

Temperatura di conservazione

2-8°C

Stringa SMILE

O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O
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
SLWWJZMPHJJOPH-PHDIDXHHSA-N

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Categorie correlate

Applicazioni

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.

Azioni biochim/fisiol

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

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 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCF9600
BCCD0595
BCCB5782
BCBW9429
BCBS8228V

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Ampicillina

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
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
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

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