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A7289912

Shikimic acid , Analysis of standard products, ≥98% , 138-59-0

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

Pack Size Price Stock Quantity
10MG RMB68.80 In Stock
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Update time: 2022-07-08

PRODUCT 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
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℃

Description and Uses

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.

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.

Safety

Symbol(GHS) 
GHS05
Signal word  Danger
Hazard statements  H318
Precautionary statements  P280-P305+P351+P338
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
Toxicity LD5 i.p. in mice: 1000 mg/kg (Evans, Osman)

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