ChemicalBook > CAS DataBase List > Shikimic acid

Shikimic acid

Product Name
Shikimic acid
CAS No.
138-59-0
Chemical Name
Shikimic acid
Synonyms
Shikimate;sikimic acid;(-)-SHIKIMIC ACID;Skikimic acid;L-SHIKIMIC ACID;Kava root extract;(3R,4S,5R)-3,4,5-TRIHYDROXY-1-CYCLOHEXENECARBOXYLIC ACID;(3R,4S,5R)-3,4,5-TRIHYDROXY-CYCLOHEX-1-ENECARBOXYLIC ACID;Shikimic;NSC 59257
CBNumber
CB2293550
Molecular Formula
C7H10O5
Formula Weight
174.15
MOL File
138-59-0.mol
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Shikimic acid Property

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
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S5375
Product name
Shikimic acid
Purity
≥99%
Packaging
1g
Price
$158
Updated
2024/03/01
Sigma-Aldrich
Product number
8.24476
Product name
(-)-Shikimic acid
Purity
for synthesis
Packaging
250mg
Price
$29.76
Updated
2024/03/01
Sigma-Aldrich
Product number
8.24476
Product name
(-)-Shikimic acid
Purity
for synthesis
Packaging
1g
Price
$175
Updated
2024/03/01
Sigma-Aldrich
Product number
69686
Product name
Shikimic acid
Purity
analytical standard
Packaging
50mg
Price
$147
Updated
2024/03/01
TCI Chemical
Product number
S0038
Product name
Shikimic Acid
Purity
>97.0%(T)
Packaging
100mg
Price
$23
Updated
2024/03/01
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Shikimic acid Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Shikimic acid manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Shikimic Acid 138-59-0
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-16
Hebei Mujin Biotechnology Co.,Ltd
Product
Shikimic Acid 138-59-0
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-09-08
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Shikimic acid 138-59-0
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
1000kg
Release date
2021-11-05

138-59-0, Shikimic acidRelated Search:

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

  • L-SHIKIMIC ACID
  • (3R,4S,5R)-3,4,5-TRIHYDROXY-1-CYCLOHEXENECARBOXYLIC ACID
  • (3R,4S,5R)-3,4,5-TRIHYDROXY-CYCLOHEX-1-ENECARBOXYLIC ACID
  • 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)
  • ShikiMic acid SynonyMs: 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
  • Shikimic Scid
  • Kava root extract
  • (3R,4S,5R)-3,4,5-TRIHYDROXYL-1-CYCLOHEXENE-1-CARBOXYLIC ACID
  • (3R,4S,5R)-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
  • (-)3ALPHA,4ALPHA,5BETA-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
  • 1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3,4,5-TRIHYDROXY-, (3R,4S,5R)
  • (-)-SHIKIMIC ACID
  • SHIKIMIC ACID
  • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
  • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3alpha,4alpha,5beta)]-
  • Bracken fern toxic component
  • Shikimate
  • Skikimic acid
  • Kava Kava Extract
  • 3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid (Shikimic acid)
  • Shikimic
  • (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
  • SHIKIMIC ACID 98%
  • SHIKIMIC ACID(RG)
  • 3,4,5-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
  • sikimic acid
  • Shikimik Acid
  • (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
  • NSC 59257
  • )-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
  • (-)-Shikimic acid for synthesis
  • Shikimic Acid &gt
  • Oseltamivir Impurity 93
  • (-)-Shikimicacid
  • Shikimic acid USP/EP/BP
  • Shikimic Acid / Shikimicacid
  • ShikiShikimic acidmic acid
  • Puer Natural Shikimic Acid
  • Shikimic Acid, 10 mM in DMSO
  • 138-59-0
  • C7H9O5
  • Biosynthetic precursor of aromatic amino acids, as well as many alkaloids and other aromatic metabolites.
  • Organic Building Blocks
  • Metabolomics
  • Metabolic Libraries
  • Simple Alcohols (Chiral)
  • Chiral Building Blocks
  • Amino Acid Library
  • BioChemical
  • Carboxylic Acids