A cyclohexenecarboxylic acid
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Metabolite(s)
36386Hexahydrohippuric Acid
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Shikimic Acid

Item No. 26851

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3R,4S,5R-trihydroxy-1-cyclohexene-1-carboxylic acid
CAS Number
138-59-0
Synonyms
  • (–)-Shikimic Acid
  • L-Shikimic Acid
  • NSC 59257
Molecular Formula
C7H10O5
Formula Weight
174.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 2.5 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
213 nm
SMILES
O=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](O)C1
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
InChi Key
JXOHGGNKMLTUBP-HSUXUTPPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $54

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    1 g

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    5 g

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    Product Description

    Shikimic acid is a cyclohexenecarboxylic acid originally isolated from I. religiosum.1 It is an intermediate in the biosynthesis of aromatic amino acids in plants and microorganisms. Shikimic acid is also a precursor in the synthesis of oseltamivir (Item No. 16070).2 It decreases lipid droplet accumulation in HepG2 cells and 3T3-L1 adipocytes when used at a concentration of 80 µM, as well as increases the levels of phosphorylated AMPK and decreases the levels of MID1IP1 in HepG2 and 3T3-L1 adipocytes when used at 40 µM.3 Shikimic acid increases differentiation of oligodendrocyte precursor cells in vitro.4 It decreases inflammation and demyelination in a mouse model of experimental autoimmune encephalomyelitis (EAE) when administered at doses of 50-200 mg/kg and reduces symptom progression at a dose of 100 mg/kg.4 It also induces remyelination in a model of focal demyelination induced by L-α-lysophosphatidylcholine (LPC) in mouse dorsal spinal cord.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bohm, B.A. Shikimic Acid (3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid). Chem. Rev. 65(4), 435-466 (1965).

    2. Rawat, G., Tripathi, P., and Saxena, R.K. Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application and market trends. Appl. Microbiol. Biotechnol. 97(10), 4277-4287 (2013).

    3. Kim, M.J., Sim, D.Y., Lee, H.M., et al. Hypolipogenic effect of shikimic acid via inhibition of MID1IP1 and phosphorylation of AMPK/ACC. Int. J. Mol. Sci. 20(3), E582 (2019).

    4. Lu, F., Yin, D., Pu, Y., et al. Shikimic acid promotes oligodendrocyte precursor cell differentiation and accelerates remyelination in mice. Neurosci. Bull. 35(3), 434-446 (2019).