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2922-42-1 molecular structure
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(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 and InChIs

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

Cite this record

CBID:125373 http://www.chembase.cn/molecule-125373.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
2922-42-1
MDL Number
MFCD00216518
PubChem SID
162219723
PubChem CID
439774
Wikipedia Title
3-Dehydroshikimic_acid

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.214242  H Acceptors
H Donor LogD (pH = 5.5) -3.288802 
LogD (pH = 7.4) -4.467806  Log P -1.0248979 
Molar Refractivity 38.1936 cm3 Polarizability 14.702371 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Apperance
Off-White Powder expand Show data source
Optical Rotation
[α]/D -59.0±3.0°, c = 1 in ethanol expand Show data source
Storage Condition
-20°C Freezer expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36 expand Show data source
Safety Statements
26 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C7H8O5 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 05616 external link
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 external link
A metabolite of Shikimic Acid.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lauhon, C.T. and Bartlett, P.A.: Biochemistry, 33, 14100 (1994)
  • • Balasubramanian, S., et al.: Biochemistry, 34, 341 (1994)
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PATENTS

PATENTS

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INTERNET

INTERNET

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