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HomeProduct name listShikimic acid

Shikimic acid

Synonym(s):(-)-Shikimic acid;(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid;(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid

  • CAS NO.:138-59-0
  • Empirical Formula: C7H10O5
  • Molecular Weight: 174.15
  • MDL number: MFCD00066278
  • EINECS: 205-334-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
Shikimic acid Structural

What is Shikimic acid?

Description

Shikimic acid (3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid) is a natural organic compound. Plant and microbial sources are the only sources of this compound. The isolation of shikimic acid from the fruit of Illicium religiosum was primarily reported by Ekmann in 1885. The name shikimic acid was derived from the oriental plant shikimi-no-ki in Japanese. It is now available in more quantities through the extraction from the fruit Illicium verum (Chinese star anise). This compound is generally utilized as a starting material for the industrial synthesis of the antiviral oseltamivir, a drug against the H1N1 influenza virus. It is also an essential intermediate in the biosynthesis of lignin, aromatic amino acids (phenylalanine, tyrosine, and tryptophan), and most alkaloids of plants and microorganisms[1]. The neuraminidase inhibitors oseltamivir or Tamiflu derived from the shikimic acid pathway are potent influenza viral neuraminidase inhibitors against most influenza strains ( influenza A and B infections). The mode of application is by mouth, either in the form of a pill or liquid.

Chemical properties

White Solid

The Uses of Shikimic acid

Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots. It has also been used as a substrate in shikimate kinase assay.

The Uses of Shikimic acid

Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic compounds.

What are the applications of Application

Shikimic acid is an intermediate in the biosynthesis of aromatic amino acids

Definition

ChEBI: A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and micro rganisms.

Biochem/physiol Actions

Shikimic acid is observed to be carcinogenic in rat models, when administered. It serves as a precursor for the biosynthesis of aromatic amino acids, alkaloids and other aromatic metabolites in microorganisms. Shikimic acid is known to inhibit adenosine diphosphate (ADP) induced platelet aggregation and blood coagulation in rabbits.

References

[1] Priyanka Singh. “Shikimic acid as intermediary model for the production of drugs effective against influenza virus.” Phytochemicals as Lead Compounds for New Drug Discovery 14 1 (2020): 245–256.

Properties of Shikimic acid

Melting point: 185-187 °C (lit.)
Boiling point: 225.11°C (rough estimate)
alpha  -180 º (c=4, H2O 25 ºC)
Density  1.52 g/cm3 (27.2℃)
vapor pressure  0Pa at 25℃
refractive index  -180 ° (C=1, H2O)
storage temp.  2-8°C
solubility  180g/l
form  Powder
pka pK (14.1°) 5.19
color  White to light beige or light gray
optical activity [α]/D -180.0±5.0°, c = 4 in H2O
Water Solubility  18 g/100 mL (20 ºC)
Sensitive  Hygroscopic
Merck  14,8480
BRN  4782717
CAS DataBase Reference 138-59-0(CAS DataBase Reference)
NIST Chemistry Reference Shikimic acid(138-59-0)
IARC 3 (Vol. 40, Sup 7) 1987

Safety information for Shikimic acid

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H318:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Shikimic acid

InChIKey JXOHGGNKMLTUBP-HSUXUTPPSA-N

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