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Shikimic acid

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-S3014

  • Specification : 98%

  • CAS number : 138-59-0

  • Formula : C7H10O5

  • Molecular Weight : 174.15

  • PUBCHEM ID : 8742

  • Volume : 25mg

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Catalogue Number

BF-S3014

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

174.15

Appearance

White crystalline powder

Botanical Source

fruits of Illicium verum

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(C(C=C1C(=O)O)O)O)O

Synonyms

(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid/3,4,5-Trihydroxycyclohex-1-enecarboxylic acid/3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid/(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid/EINECS 205-334-2/1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-/3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid/(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid/3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid/Shikimic Acid

IUPAC Name

(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid

Density

1.7±0.1 g/cm3

Solubility

Flash Point

210.1±25.2 °C

Boiling Point

400.5±45.0 °C at 760 mmHg

Melting Point

185-187 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:138-59-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31048002

Abstract

Shikimic acid (SA), a widely-known hydroaromatic compound enriched in Bracken fern and Illicium verum (also known as Chinese star anise), increases the risk of gastric and esophageal carcinoma, nevertheless, the influence of SA on breast cancer remains indistinct. Herein we found that, with models in vitro, SA significantly promoted estrogen receptor(ER) positive cells proliferation and NF-κB activation was involved in it. Moreover, our data showed that IκBα, a critically endogenous inhibitor of NF-κB, was repressed. Subsequently, we found increase of miR-300 by SA treatment sand miR-300 could target IκBα mRNA. Additionally, inhibition of miR-300 abrogated the repression of IκBα by SA. As a result, miR-300 was also involved in NF-κB activation and breast cancer cells proliferation promotion due to SA exposure. Taken together, with ER-positive breast cancer cell models in vitro, MCF-7 and T47D, our results implied that SA promoted breast cancer cells proliferation via a miR-300-induced NF-κB dependent pathway controlling cell cycle proteins.

KEYWORDS

ER-positive breast cancer; IκBα; NF-κB; SA.

Title

Shikimic Acid Promotes Estrogen receptor(ER)-positive Breast Cancer Cells Proliferation via Activation of NF-κB Signaling

Author

Xiao Ma 1 , Shilong Ning 2

Publish date

2019 Sep 15

PMID

25563634

Abstract

The sudden outbreak of swine flu has increased the global demand of shikimic acid which is an industrially interesting compound, as it is used as a key starting material for the synthesis of a neuraminidase inhibitor Tamiflu(®), for the treatment of antiviral infections such as swine flu. Statistical optimization and evaluation of medium components for the production of shikimic acid by Citrobacter freundii is addressed in the present investigation. Plackett-Burman design was applied for the screening of the most significant variables affecting shikimic acid production, where glucose, asparagine, KH2PO4, CaCO3 and agitation rate were the most significant factors. Response surface methodology was also employed to study the interaction among the most significant variables through which shikimic acid production increased to 12.76 g/L. Further, fed-batch studies resulted in the production of 22.32 g/L of shikimic acid. The scalability of the process was also confirmed by running 14 L bioreactor (7.5 L production medium) where 20.12 g/L of shikimic acid was produced. In addition the antibacterial activity of the shikimic acid produced was analysed against four Gram positive and four Gram negative bacteria and it was found to have a greater inhibition effect against the Gram negative bacteria.

Title

Shikimic Acid, a Base Compound for the Formulation of Swine/Avian Flu Drug: Statistical Optimization, Fed-Batch and Scale Up Studies Along With Its Application as an Antibacterial Agent

Author

P Tripathi 1 , G Rawat, S Yadav, R K Saxena

Publish date

2015 Feb

PMID

30227208

Abstract

This study investigated the impact of Shikimic Acid (SA) obtained from leaves of Artemisia absinthium on protein glycation in the retina of diabetic rats. The GC/MS analysis of A. absinthium showed that the most abundant bioactive compound was SA (C7H10O5) with a measured retention Index (RI) of 1960 compared to that of the reference sample (1712). Male albino rats were divided into two main groups, Group I (control) and Group II (diabetic); Group II was further divided into four subgroups: Group IIa (diabetic control), Group IIb (diabetic rats were given SA orally [50 mg/kg, body weight (bw)/day], Group IIc diabetic rats were given SA orally [100 mg/kg, bw/day], and Group IId (diabetic rats were given metformin orally [100 mg/kg, bw/day] as positive control). The data obtained suggested that SA reduced glucose and glycated hemoglobin levels. In addition, SA also decreased the formation of glucose-derived advanced glycation end products. Interestingly, SA showed interference with the release of inflammatory mediators in retina and possess antioxidant potential. In conclusion, SA protected the tissues from detrimental effects of hyperglycemia and enhanced antioxidant activity. SA could be a potential lead in the process of drug development in the future to prevent retinopathy in diabetic subjects.

KEYWORDS

Antiglycation; Artemisia absinthium; Diabetic rats; Hyperglycemia; Retinopathy; Shikimic acid.

Title

Shikimic Acid From Artemisia Absinthium Inhibits Protein Glycation in Diabetic Rats

Author

Abdulrahman L Al-Malki 1

Publish date

2019 Feb 1


Description :

Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants.