Shikimic acid Chemical Properties

Melting point:

185-187 °C (lit.)

alpha 

-180 º (c=4, H2O 25 ºC)

Boiling point:

225.11°C (rough estimate)

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

InChIKey

JXOHGGNKMLTUBP-HSUXUTPPSA-N

LogP

-1.5 at 21℃ and pH1

Surface tension

49.86mN/m at 1g/L and 20℃

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

GW4600000

F 

3-10

HS Code 

29181980

Hazardous Substances Data

138-59-0(Hazardous Substances Data)

Toxicity

LD5 i.p. in mice: 1000 mg/kg (Evans, Osman)

MSDS

• Language:English Provider:Shikimic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Shikimic acid Usage And Synthesis

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

Uses

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.

Uses

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.

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.

Shikimic acid(138-59-0)Related Product Information

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