Shikimic acid | CAS:138-59-0 | Manufacturer ChemFaces

Shikimic acid

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Description:

Shikimic acid(Shikimate), more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms, has great potential for the design and synthesis of enzyme inhibitors. It reversed the H2O2 induced oxidative damage in hepatocytes, probably through the inhibition of NF-κB, with the activation of PI3K/Akt/Nrf2 pathway and reduction of apoptosis by interfering the SAPK/JNK/Bax pathway; it also profoundly inhibited pancreatic lipase activity by 66%, thus providing another valuable therapeutic aspect for treating diet induced obesity in humans.

Targets:

ROS | NF-kB | JNK | Bcl-2/Bax | Nrf2 | SAPK | Akt

In vitro:

Antonie Van Leeuwenhoek. 2015 Feb;107(2):419-31.

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.[Pubmed: 25563634]

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

Shikimic acid Description

Source:	The fruits of Illicium verum.
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Bioresour Technol. 2013 Sep;144:675-9.

An interactive study of influential parameters for shikimic acid production using statistical approach, scale up and its inhibitory action on different lipases.[Pubmed: 23871288]

Shikimic acid is the promising candidate as a building block for the industrial synthesis of drug Tamiflu used for the treatment of Swine flu. The fermentative production process using microbes present an excellent and even more sustainable alternative to the traditional plants based extraction methods.
CONCLUSIONS:
In the present study, the fermentative production of Shikimic acid by Citrobacter freundii GR-21 (KC466031) was optimized by process engineering using a statistical modeling approach and a maximum amount of 16.78 g L(-1) was achieved. The process was also scaled up to 14L bioreactor to validate the production of Shikimic acid. Further, the potential of anti-enzymatic nature of purified Shikimic acid was evaluated for different lipases wherein, Shikimic acid inhibited the hydrolysis of triglycerides by 55-60%.
CONCLUSIONS:
Shikimic acid also profoundly inhibited pancreatic lipase activity by 66%, thus providing another valuable therapeutic aspect for treating diet induced obesity in humans.

Cell Research:

J Ethnopharmacol. 2014 Aug 8;155(1):132-46.

Protective effect of coconut water concentrate and its active component shikimic acid against hydroperoxide mediated oxidative stress through suppression of NF-κB and activation of Nrf2 pathway.[Pubmed: 24835026]

Conventionally coconut water has been used as an 'excellent hydrating' drink that maintain the electrolyte balance and help in treating diverse ailments related to oxidative stress including liver function. The present study was aimed to elucidate whether and how the coconut water concentrate (CWC) and its major active phytoconstituent Shikimic acid (SA) can effectively protect murine hepatocytes from the deleterious effect of hydroperoxide-mediated oxidative stress.
METHODS AND RESULTS:
Bioactivity guided fractionation of CWC resulted in the isolation of a couple of known compounds. Freshly isolated murine hepatocytes were exposed to hydrogen peroxide (H2O2) (1 and 3mM) in the presence or absence of CWC (200 and 400 μg/ml) and SA (40 μM) for the determination of antioxidative, DNA protective, cellular ROS level by modern methods, including immunoblot and flowcytometry to find out the possible mechanism of action. Pre-treatment of hepatocyte with CWC and SA showed significant prevention of H2O2-induced intracellular ROS generation, nuclear DNA damage along with the formation of hepatic TBARS and cellular nitrite. Further, the H2O2 induced cell death was arrested in the presence of CWC through the inhibition of CDC42 mediated SAPK/JNK pathways and activation of other molecules of apoptotic pathways, including Bax and caspase3. Moreover, CWC and SA help in maintaining the GSH level and endogenous antioxidants like Mn-SOD, to support intracellular defense mechanisms, probably through the transcriptional activation of Nrf2; and inhibition of nuclear translocation of NF-κB.
CONCLUSIONS:
CWC and its active components SA reversed the H2O2 induced oxidative damage in hepatocytes, probably through the inhibition of NF-κB, with the activation of PI3K/Akt/Nrf2 pathway and reduction of apoptosis by interfering the SAPK/JNK/Bax pathway.

Product Name	Shikimic acid
Price:	$30 / 20mg
CAS No.:	138-59-0
Catalog No.:	CFN99436
Molecular Formula:	C₇H₁₀O₅
Molecular Weight:	174.2 g/mol
Purity:	>=98%
Type of Compound:	Miscellaneous
Physical Desc.:	Powder
Source:	The fruits of Illicium verum.
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antimalaric Compound Library Precursors Compound Library Antimicrobial Compound Library Miscellaneous Compound Library ROS Inhibitor Library Nrf2 Inhibitor Library NF-kB Inhibitor Library JNK Inhibitor Library Bcl-2/Bax Inhibitor Library Akt Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.7405 mL	28.7026 mL	57.4053 mL	114.8106 mL	143.5132 mL
5 mM	1.1481 mL	5.7405 mL	11.4811 mL	22.9621 mL	28.7026 mL
10 mM	0.5741 mL	2.8703 mL	5.7405 mL	11.4811 mL	14.3513 mL
50 mM	0.1148 mL	0.5741 mL	1.1481 mL	2.2962 mL	2.8703 mL
100 mM	0.0574 mL	0.287 mL	0.5741 mL	1.1481 mL	1.4351 mL

CFN98778	vibo-Quercitol	488-76-6	164.2	C₆H₁₂O₅
CFN91718	Inositol	87-89-8	180.16	C₆H₁₂O₆
CFN95609	(E)-1-methoxy-2-O-(p-coumaroyl)-myo-inositol	1391715-18-6	340.3	C₁₆H₂₀O₈
CFN99044	D-Pinitol	10284-63-6	194.2	C₇H₁₄O₆
CFN90586	L-Quebrachitol	642-38-6	194.18	C₇H₁₄O₆
CFN98868	Conduritol A	526-87-4	146.1	C₆H₁₀O₄
CFN99930	D-(-)-Quinic acid	77-95-2	192.17	C₇H₁₂O₆
CFN99436	Shikimic acid	138-59-0	174.2	C₇H₁₀O₅
CFN99852	3,4-O-Isopropylidene shikimic acid	183075-03-8	214.2	C₁₀H₁₄O₅
CFN92951	3-O-Caffeoylshikimic acid	180981-12-8	336.29	C₁₆H₁₆O₈