An esterified form of mycophenolic acid
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Mycophenolic Acid methyl ester

Item No. 38397

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid, methyl ester
CAS Number
31858-66-9
Synonyms
  • Methyl Mycophenolate
  • MPA methyl ester
Molecular Formula
C18H22O6
Formula Weight
334.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 3 mg/ml
λmax
216 nm
SMILES
CC1=C2C(C(OC2)=O)=C(C(C/C=C(C)/CCC(OC)=O)=C1OC)O
InChi Code
InChI=1S/C18H22O6/c1-10(6-8-14(19)22-3)5-7-12-16(20)15-13(9-24-18(15)21)11(2)17(12)23-4/h5,20H,6-9H2,1-4H3/b10-5+
InChi Key
ZPXRQFLATDNYSS-BJMVGYQFSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Mycophenolic acid methyl ester is an esterified form of the immunosuppressive microbial metabolite mycophenolic acid (Item No. 21716) that has been found in P. spartinae.1 It inhibits transactivation of peroxisome proliferator-activated receptor γ (PPARγ) induced by the PPARγ agonist pioglitazone (Item Nos. 71745 | 22263 | 10028) in U2OS cells in a reporter assay when used at concentrations of 1 and 10 µM.2 Mycophenolic acid methyl ester is cytotoxic against a panel of seven cancer cell lines (IC50s = 0.26-23.73 µM).3 It inhibits tumor growth in an Ehrlich murine spontaneous adenocarcinoma model and decreases the production of antibodies against sheep red blood cells in mice when administered at a dose of 120 mg/kg.4 Mycophenolic acid methyl ester has been used as a precursor in the synthesis of mycophenolic acid β-D-glucuronide (Item No. 19078).5 It is also a potential impurity in commercial preparations of the mycophenolic acid prodrug mycophenolate mofetil.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elsebai, M.F. Secondary metabolites from the marine-derived fungus Phaeosphaeria spartinae. Nat. Prod. Res. 35(9), 1504-1509 (2021).

    2. Ubukata, M., Takamori, H., Ohashi, M., et al. Mycophenolic acid as a latent agonist of PPARγ. Bioorg. Med. Chem. Lett. 17(17), 4767-4770 (2007).

    3. Silalai, P., Pruksakorn, D., Chairoungdua, A., et al. Synthesis of propargylamine mycophenolate analogues and their selective cytotoxic activity towards neuroblastoma SH-SY5Y cell line. Bioorg. Med. Chem. Lett. 45, 128135 (2021).

    4. Oshugi, Y., Suzuki, S., and Takagaki, Y. Antitumor and immunosuppressive effects of mycophenolic acid derivatives. Cancer Res. 36(8), 2923-2927 (1976).

    5. Jones, A.E., Wilson, H.K., Meath, P., et al. Convenient syntheses of the in vivo carbohydrate metabolites of mycophenolic acid: Reactivity of the acyl glucuronide. Tetrahedron Lett. 50(35), 4973-4977 (2009).

    6. Lu, Y.T., Qi, W.Z., Chen, Y.F., et al. Separation and identification of process-related substances and degradation products in mycophenolate mofetil by liquid chromatography coupled with quadrupole-time of flight mass spectrometry. J. Sep. Sci. 42(16), 2650-2659 (2019).