(E/Z)-Methyl mycophenolate is the mixture of E and Z-configurational isomers of Methyl mycophenolate which is the methyl ester of mycophenolic acid and an impurity of Mycophenolate mofetil. Methyl mycophenolate is a prodrug of mycophenolic acid (MPA). It is a naturally occuring compound isolated from marine-derived fungus Phaeosphaeria spartinae and acts as an inhibitor of inosine monophosphate dehydrogenase (IMPDH).

Physicochemical Properties

Molecular Formula	C18H22O6
Molecular Weight	334.36368
Exact Mass	334.142
CAS #	24243-40-1
Related CAS #	Methyl mycophenolate;31858-66-9
PubChem CID	6478685
Appearance	Typically exists as solid at room temperature
LogP	2.821
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Heavy Atom Count	24
Complexity	500
Defined Atom Stereocenter Count	0
SMILES	CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OC)O
InChi Key	ZPXRQFLATDNYSS-BJMVGYQFSA-N
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+
Chemical Name	methyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
Synonyms	Methyl mycophenolate; 31858-66-9; Methyl Mycophenolate (EP Impurity E); Mycophenolic Acid Methyl Ester; (E/Z)-Methyl mycophenolate; 24243-40-1; methyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate; 0B5C0EG8E8;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Impurity of Mycophenolate mofetil
References	[1]. Convenient syntheses of the in vivo carbohydrate metabolites. Tetrahedron Letters. 50 (2009): 4973-4977. [2]. Synthesis of mycophenolic acid beta-D-glucuronide and its antitumor activity. J Antibiot (Tokyo). 1970 Aug;23(8):408-13.
Additional Infomation	Following in vivo use of mycophenolic acid, the O-aryl and O-acyl glucuronides, as well as the recently discovered O-aryl glucoside (Scheme 1), are all found as metabolites. We describe convenient preparations of all three derivatives. The phenolic glycosides are obtained by phase-transfer-catalysed alkylation of methyl mycophenolate in very high yield, as an excellent alternative to the Königs-Knorr reaction. We carefully optimised our earlier synthesis of the acyl glucuronide to give a highly pure product in a much improved yield. Finally, we describe the value of a synthetic acyl glucuronide in demonstrating its reactivity towards a known target protein with superior response to the naturally obtained material.[1]

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9908 mL	14.9539 mL	29.9079 mL
	5 mM	0.5982 mL	2.9908 mL	5.9816 mL
	10 mM	0.2991 mL	1.4954 mL	2.9908 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.