Shikimic acid | CAS# 138-59-0 | Acid

MedKoo Cat#: 574129 | Name: Shikimic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Shikimic acid is a cyclohexenecarboxylic acid intermediate in the biosynthesis of aromatic amino acids in plants and microorganisms. Shikimic acid is also a precursor in the synthesis of oseltamivir. It decreases lipid droplet accumulation, increases the levels of phosphorylated AMPK, and decreases the levels of MID1IP1. Shikimic acid increases differentiation of oligodendrocyte precursor cells in vitro. It decreases inflammation and demyelination in a mouse model of experimental autoimmune encephalomyelitis (EAE) and induces remyelination in a model of focal demyelination induced by L-α-lysophosphatidylcholine (LPC) in mouse dorsal spinal cord.

Chemical Structure

Shikimic acid

CAS#138-59-0

Theoretical Analysis

MedKoo Cat#: 574129

Name: Shikimic acid

CAS#: 138-59-0

Chemical Formula: C7H10O5

Exact Mass: 174.0528

Molecular Weight: 174.15

Elemental Analysis: C, 48.28; H, 5.79; O, 45.93

Price and Availability

Size	Price	Availability
250mg	USD 300.00	2 weeks
500mg	USD 500.00	2 weeks
1g	USD 750.00	2 weeks
5g	USD 1,400.00	2 weeks

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Synonym

(–)-Shikimic Acid, L-Shikimic Acid, Shikimic acid

IUPAC/Chemical Name

3R,4S,5R-trihydroxy-1-cyclohexene-1-carboxylic acid

InChi Key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

InChi Code

InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

SMILES Code

O=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](O)C1

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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

In vitro activity:

The results of this study implied that shikimic acid promoted breast cancer cells proliferation via a miR-300-induced NF-κB dependent pathway controlling cell cycle proteins. In an in vitro model of breast cancer, shikimic acid significantly promoted estrogen receptor (ER) positive cells proliferation. There was an increase of miR-300 by shikimic acid treatment and miR-300 could target IκBα mRNA. Reference: Toxicol Lett. 2019 Sep 15;312:65-71. https://pubmed.ncbi.nlm.nih.gov/31048002/

In vivo activity:

In an SD rat model, shikimic acid had anti-diarrheal activity. Shikimic acid rescued diarrhea and its complications by restoring kidney function, serum and urinary electrolytes, antioxidant activity, inflammatory markers, sodium/potassium-ATPase activity, the apoptosis genes, and the histology of the kidney in diarrheal rats to approach the control one. Reference: Lab Anim Res. 2023 Nov 10;39(1):28. https://pubmed.ncbi.nlm.nih.gov/37950334/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	143.55
	DMSO	25.0	143.55
	Ethanol	2.5	14.36

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 174.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ma X, Ning S. Shikimic acid promotes estrogen receptor(ER)-positive breast cancer cells proliferation via activation of NF-κB signaling. Toxicol Lett. 2019 Sep 15;312:65-71. doi: 10.1016/j.toxlet.2019.04.030. Epub 2019 Apr 29. PMID: 31048002. 2. Rabelo TK, Zeidán-Chuliá F, Caregnato FF, Schnorr CE, Gasparotto J, Serafini MR, de Souza Araújo AA, Quintans-Junior LJ, Moreira JCF, Gelain DP. In Vitro Neuroprotective Effect of Shikimic Acid Against Hydrogen Peroxide-Induced Oxidative Stress. J Mol Neurosci. 2015 Aug;56(4):956-965. doi: 10.1007/s12031-015-0559-9. Epub 2015 Apr 11. PMID: 25862258. 3. Bao X, Zheng Z, Lv J, Bao J, Chang S, Jiang X, Xin Y. Shikimic acid (SA) inhibits neuro-inflammation and exerts neuroprotective effects in an LPS-induced in vitro and in vivo model. Front Pharmacol. 2023 Nov 2;14:1265571. doi: 10.3389/fphar.2023.1265571. PMID: 38026972; PMCID: PMC10652795. 4. Koriem KMM, Abdeen AMA. Shikimic acid recovers diarrhea and its complications in SD rats fed lactose diet to induce diarrhea. Lab Anim Res. 2023 Nov 10;39(1):28. doi: 10.1186/s42826-023-00179-y. PMID: 37950334; PMCID: PMC10636980.

In vitro protocol:

In vivo protocol:

1. Bao X, Zheng Z, Lv J, Bao J, Chang S, Jiang X, Xin Y. Shikimic acid (SA) inhibits neuro-inflammation and exerts neuroprotective effects in an LPS-induced in vitro and in vivo model. Front Pharmacol. 2023 Nov 2;14:1265571. doi: 10.3389/fphar.2023.1265571. PMID: 38026972; PMCID: PMC10652795. 2. Koriem KMM, Abdeen AMA. Shikimic acid recovers diarrhea and its complications in SD rats fed lactose diet to induce diarrhea. Lab Anim Res. 2023 Nov 10;39(1):28. doi: 10.1186/s42826-023-00179-y. PMID: 37950334; PMCID: PMC10636980.

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