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
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
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)
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.
N-Bromosuccinimide Price
- Product number
- S5375
- Product name
- Shikimic acid
- Purity
- ≥99%
- Packaging
- 1g
- Price
- $158
- Updated
- 2024/03/01
- Product number
- 8.24476
- Product name
- (-)-Shikimic acid
- Purity
- for synthesis
- Packaging
- 250mg
- Price
- $29.76
- Updated
- 2024/03/01
- Product number
- 8.24476
- Product name
- (-)-Shikimic acid
- Purity
- for synthesis
- Packaging
- 1g
- Price
- $175
- Updated
- 2024/03/01
- Product number
- 69686
- Product name
- Shikimic acid
- Purity
- analytical standard
- Packaging
- 50mg
- Price
- $147
- Updated
- 2024/03/01
- Product number
- S0038
- Product name
- Shikimic Acid
- Purity
- >97.0%(T)
- Packaging
- 100mg
- Price
- $23
- Updated
- 2024/03/01
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
- Product
- shikimic acid 138-59-0
- Price
- US $160.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2021-07-21
- Product
- Shikimic acid 138-59-0
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 99.99%
- Supply Ability
- 20 tons
- Release date
- 2024-04-07
- Product
- Shikimic acid 138-59-0
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20tons
- Release date
- 2024-04-03