(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 125373
• Molecular Formular: C7H8O5
• Molecular Mass: 172.13542
• Monoisotopic Mass: 172.03717336
• SMILES: O=C1C=C(C(=O)O)C[C@@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1CC(=CC(=O)[C@H]1O)C(=O)O
• InChI: 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
• InChIKey: SLWWJZMPHJJOPH-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: 3-dehydroshikimic acid
• Synonyms: 3-Dehydroshikimate; 3-DHS; (-)-3-DHS; 3-Dehydroshikimic acid; (4S,5R)-(-)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid; 5-Dehydroshikimic acid; 3-Dehydroshikimic acid; DHS, 5-Dehydroshikimic Acid, 1-Cyclohexene-1-carboxylic Acid, 4,5-Dihydroxy-3-oxo trans; (-)-3-Dehydro Shikimic Acid

Database IDs

• CAS Number: 2922-42-1
• MDL Number: MFCD00216518
• PubChem SID: 162219723
• PubChem CID: 439774
• Wikipedia Title: 3-Dehydroshikimic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.214242
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.288802
• LogD (pH = 7.4): -4.467806
• Log P: -1.0248979
• Molar Refractivity: 38.1936 cm^3
• Polarizability: 14.702371 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White Powder
• Optical Rotation: [α]/D -59.0±3.0°, c = 1 in ethanol

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C7H8O5

DETAILS

Sigma Aldrich - 05616

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

Toronto Research Chemicals - D230475

A metabolite of Shikimic Acid.

REFERENCES

• Lauhon, C.T. and Bartlett, P.A.: Biochemistry, 33, 14100 (1994)
• Balasubramanian, S., et al.: Biochemistry, 34, 341 (1994)