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ChemicalBook > Product Catalog >Biochemical Engineering >Natural Products >Shikimic acid

Shikimic acid

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CAS:138-59-0
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CAS:138-59-0
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CAS:138-59-0
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Shikimic acid Basic information
Product Name:Shikimic acid
Synonyms:Shikimic acid,(3R,4S,5R)-()-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid;Illicium Verum P.E.;Shikimic acid methyl esther;ShikiMic acid, 98% 1GR;3,4,5-Trihydroxycyclohex-1-enecarboxylic acid;Shikimic acid,98%;ShikiMic acid API;ShikiMic acid (ShikiMate)
CAS:138-59-0
MF:C7H10O5
MW:174.15
EINECS:205-334-2
Product Categories:Inhibitors;Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;API;Antibiotic;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Natural Plant Extract;Chiral Reagents;API intermediates;138-59-0
Mol File:138-59-0.mol
Shikimic acid Structure
Shikimic acid Chemical Properties
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
pkapK (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
InChIKeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
LogP-1.5 at 21℃ and pH1
Surface tension49.86mN/m at 1g/L and 20℃
CAS DataBase Reference138-59-0(CAS DataBase Reference)
NIST Chemistry ReferenceShikimic acid(138-59-0)
IARC3 (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
3-10
HS Code 29181980
Hazardous Substances Data138-59-0(Hazardous Substances Data)
ToxicityLD5 i.p. in mice: 1000 mg/kg (Evans, Osman)
MSDS Information
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Shikimic acid English
SigmaAldrich English
ACROS English
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Shikimic acid Usage And Synthesis
DescriptionShikimic 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 PropertiesWhite Solid
UsesShikimic 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.
UsesNaturally 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.
DefinitionChEBI: 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 ActionsShikimic 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.
Tag:Shikimic acid(138-59-0) Related Product Information
3-O-Caffeoylshikimic acid 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))- shikimic acid-3-phosphate ASTRAGALIN Shikimic acid 1-Cyclohexene-1-carboxylic acid Luteolin Coumalic acid (3R,4R,5R)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (3aR,7R,7aR)-2,2-Diethyl-3a,6,7,7a-tetrahydro-7-[(Methylsulfonyl)oxy]-1,3-benzodioxole-5-carboxylic Acid Ethyl Ester Oseltamivir Impurity 150 4-N-Desacetyl-5-N-acetyl OseltaMivir Protocatechuic acid Scutellarin Dehydroshikimic acid Ethanol Sodium bicarbonate Oxalic acid dihydrate