3-Dehydroshikimic acid
SIGMA/05616 - ≥95.0% (HPLC)
Synonym: (4S,5R)-(−)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid; 3-DHS; 5-Dehydroshikimic acid
CAS Number: 2922-42-1
Empirical Formula (Hill Notation): C7H8O5
Molecular Weight: 172.14
MDL Number: MFCD00216518
Linear Formula: C7H8O5
Product Type: Chemical
| assay | ≥95.0% (HPLC) |
| form | powder |
| InChI | 1S/C7H8O5/c8-4-1-3(7(11)1 |
| InChI key | SLWWJZMPHJJOPH-PHDIDXHHSA |
| optical activity | [α]/D -59.0±3.0°, c = 1 in ethanol |
| Quality Level | 100  |
| SMILES string | O[C@@H]1CC(=CC(=O)[C@H]1O |
| storage temp. | 2-8°C |
| 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. |
| Other Notes: | Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 05616.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin. |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H319 |
| Precautionary statements | P305 + P351 + P338 |
| Hazard Codes | Xi |
| Risk Statements | 36 |
| Safety Statements | 26 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥95.0% (HPLC) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352200 |