3,4,5-Trihydroxycyclohex-1-enecarboxylic acid, CAS No. 138-59-0

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138-59-0

Catalog No. EBD2197575

CAS 138-59-0

Name 3,4,5-Trihydroxycyclohex-1-enecarboxylic acid

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Basic Information

Synonyms: Shikimicacid (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylicacid (-)-Shikimicacid 3,4,5-trihydroxycyclohex-1-ene-1-carboxylicacid (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylicacid (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylicacid 3,4,5-Trihydroxycyclohex-1-enecarboxylicacid

Molecular Formula: C7H10O5

Molecular Weight: 174.15

MDL Number: MFCD00066278

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Phytochemicals and Natural Products

Product Description:

Shikimic acid is a naturally occurring cyclohexene carboxylic acid with three hydroxyl groups, systematically named 3,4,5-trihydroxycyclohex-1-enecarboxylic acid. It is a key biochemical intermediate in the shikimate pathway, which is essential for the biosynthesis of aromatic amino acids in plants, bacteria, and fungi but absent in mammals. This compound is most prominently known as the primary precursor for the industrial synthesis of the antiviral drug oseltamivir phosphate (Tamiflu), used to treat influenza A and B. It also serves as a versatile chiral building block for synthesizing various bioactive natural products and pharmaceutical intermediates. Beyond its role in drug synthesis, shikimic acid exhibits antioxidant, anti-inflammatory, and neuroprotective properties, making it a subject of interest in nutraceutical and biomedical research.

Physical Properties

Melting Point: 185-187 °C(lit.)

Boiling Point: 400.5 ºC at 760 mmHg

Flash Point: 210.1 ºC

Density: 1.725 g/cm3

Solubility: water: 18 g/100 mL (20 ºC)

Refractivity: -180 ° (C=1, H2O)

Analytical Data

Appearance: white solid