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Name |
Mycophenolic acid |
EINECS | 246-119-3 |
CAS No. | 24280-93-1 | Density | 1.29 g/cm3 |
PSA | 93.06000 | LogP | 2.73320 |
Solubility | Almost insoluble in cold water. Soluble in alcohol | Melting Point |
141 °C |
Formula | C17H20O6 | Boiling Point | 611.6 °C at 760 mmHg |
Molecular Weight | 320.342 | Flash Point | 225.8 °C |
Transport Information | N/A | Appearance | White to off-white powder |
Safety | 53-45-36/37 | Risk Codes | 22-61-40 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
4-Hexenoic acid,6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (E)- (8CI);(E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoicacid;Melbex; |
Article Data | 27 |
ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate
mycophenolic acid
Conditions | Yield |
---|---|
With lithium hydroxide In methanol for 12h; | 98% |
With lithium hydroxide In methanol at 23℃; for 5h; | 93% |
With lithium hydroxide In methanol; water at 25℃; for 1h; | 71% |
methyl mycophenolate
mycophenolic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; water at 25℃; for 24h; | 96% |
With lithium hydroxide In tetrahydrofuran for 3h; Ambient temperature; | 85% |
With water; lithium hydroxide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 66% |
7-hydroxy-6-[(E)-6-hydroxy-3-methylhex-2-enyl]-5-methoxy-4-methyl-3H-2-benzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
With jones reagent In acetone at -30℃; for 5h; | 61% |
D-glucose
mycophenolic acid
Conditions | Yield |
---|---|
With manganese(II) sulfate; potassium permanganate; potassium dihydrogenphosphate; L-methionine; Penicillium brevicompactum No. 4-23-11 spores; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; glycine; zinc(II) sulfate In water at 26℃; for 360h; Product distribution; effect of the spore concentration, effect of addition of various adsorbents; | |
With manganese(II) sulfate; potassium permanganate; potassium dihydrogenphosphate; L-methionine; Celite; Penicillium brevicompactum No. 4-23-11 spores; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; glycine; zinc(II) sulfate In water at 26℃; for 360h; Product distribution; various drug-resistant, methionine or glutamate auxotrophic mutants, effect of L-methionine concentration, effect of L-glutamate concentration; |
7-O-Methylmycophenolic acid
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 189 mg / ethyl acetate 2: BCl3 / CH2Cl2 / 12 h / 20 °C 3: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: ethyl acetate 2: 86 percent / BCl3 / CH2Cl2 / 192 h 3: LiOH / H2O View Scheme |
5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BCl3 / CH2Cl2 / 12 h / 20 °C 2: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 86 percent / BCl3 / CH2Cl2 / 192 h 2: LiOH / H2O View Scheme |
(E)-6-(4,6-Dimethoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enal
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Jones reagent / acetone / 4 h / -30 °C 2: 189 mg / ethyl acetate 3: BCl3 / CH2Cl2 / 12 h / 20 °C 4: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: CrO3, acid / acetone / -30 °C 2: ethyl acetate 3: 86 percent / BCl3 / CH2Cl2 / 192 h 4: LiOH / H2O View Scheme |
6-((E)-3,7-Dimethyl-octa-2,6-dienyl)-5,7-dimethoxy-4-methyl-3H-isobenzofuran-1-one
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: O3 / methanol / -78 °C 1.2: Me2S / methanol / 3 h / -10 - 20 °C 2.1: Jones reagent / acetone / 4 h / -30 °C 3.1: 189 mg / ethyl acetate 4.1: BCl3 / CH2Cl2 / 12 h / 20 °C 5.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 2: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 3: Jones reagent / acetone / 4 h / -30 °C 4: 189 mg / ethyl acetate 5: BCl3 / CH2Cl2 / 12 h / 20 °C 6: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: O3, Me2S / CH2Cl2; pyridine / -78 °C 2: CrO3, acid / acetone / -30 °C 3: ethyl acetate 4: 86 percent / BCl3 / CH2Cl2 / 192 h 5: LiOH / H2O View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-2,4-dimethoxy-5-methyl-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 100 percent / K2CO3 / methanol / 6 h 2.1: O3 / methanol / -78 °C 2.2: Me2S / methanol / 3 h / -10 - 20 °C 3.1: Jones reagent / acetone / 4 h / -30 °C 4.1: 189 mg / ethyl acetate 5.1: BCl3 / CH2Cl2 / 12 h / 20 °C 6.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: 100 percent / K2CO3 / methanol / 6 h 2: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 3: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 4: Jones reagent / acetone / 4 h / -30 °C 5: 189 mg / ethyl acetate 6: BCl3 / CH2Cl2 / 12 h / 20 °C 7: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: K2CO3 / methanol 2: O3, Me2S / CH2Cl2; pyridine / -78 °C 3: CrO3, acid / acetone / -30 °C 4: ethyl acetate 5: 86 percent / BCl3 / CH2Cl2 / 192 h 6: LiOH / H2O View Scheme |
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-5-formyl-2,4-dimethoxy-benzoic acid methyl ester
mycophenolic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 89 percent / NaBH4 / methanol / 0.5 h 2.1: Et3N / CH2Cl2 / 2.5 h / 25 °C 3.1: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 4.1: 100 percent / K2CO3 / methanol / 6 h 5.1: O3 / methanol / -78 °C 5.2: Me2S / methanol / 3 h / -10 - 20 °C 6.1: Jones reagent / acetone / 4 h / -30 °C 7.1: 189 mg / ethyl acetate 8.1: BCl3 / CH2Cl2 / 12 h / 20 °C 9.1: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1: 89 percent / NaBH4 / methanol / 0.5 h 2: Et3N / CH2Cl2 / 2.5 h / 25 °C 3: 372 mg / NaBH4 / dimethylformamide / 2.5 h / 25 °C 4: 100 percent / K2CO3 / methanol / 6 h 5: 75.4 percent / NaOAc; m-CPBA / CH2Cl2 / 7 h / -70 °C 6: HIO4*2H2O / diethyl ether; tetrahydrofuran / 1 h / 0 °C 7: Jones reagent / acetone / 4 h / -30 °C 8: 189 mg / ethyl acetate 9: BCl3 / CH2Cl2 / 12 h / 20 °C 10: 92 mg / LiOH / methanol; H2O / 6 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1: 89 percent / NaBH4 / methanol 2: Et3N / CH2Cl2 / 1.5 h 3: NaBH4 / dimethylformamide 4: K2CO3 / methanol 5: O3, Me2S / CH2Cl2; pyridine / -78 °C 6: CrO3, acid / acetone / -30 °C 7: ethyl acetate 8: 86 percent / BCl3 / CH2Cl2 / 192 h 9: LiOH / H2O View Scheme |
Molecular Structure of Mycophenolic acid (CAS NO.24280-93-1):
CAS Number: 24280-93-1
Molecular Formula: C17H20O6
Molecular Weight: 320.37
H bond acceptors: 6
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 71.06 Å2
EINECS: 246-119-3
Density: 1.29 g/cm3
Melting Point: 141oC
Boiling Point: 611.6oC at 760 mmHg
Flash Point: 225.8oC
Solubility: Almost insoluble in cold water. Soluble in alcohol
Appearance: White to off-white powder
Properties: Needles from hot water.
Storage temp: 2-8oC
Solubility:methanol: 50 mg/mL, clear, colorless to faintly yellow
Form: powder
Merck: 13,6352
Product Categories: Active Pharmaceutical Ingredients; Aromatics Compounds; Aromatics; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
InChI
InChI=1/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
Smiles
c12c(c(c(C\C=C(\CCC(O)=O)C)c(c1C)OC)O)C(=O)OC2
1. | dni-mus:lym 200 nmol/L | CNREA8 Cancer Research. 45 (1985),5512. | ||
2. | oms-mus:lym 400 nmol/L | CNREA8 Cancer Research. 45 (1985),5512. | ||
3. | orl-rat LD50:352 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
4. | ivn-rat LD50:450 mg/kg | PMDCAY Progress in Medical Chemistry. 9 (1973),1. | ||
5. | ipr-rat LD50:220 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
6. | scu-rat LD50:230 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
7. | orl-mus LDLo:1000 mg/kg | 85GDA2 CRC Handbook of Antibiotic Compounds, Volumes 1-9. 5 (1981),445. | ||
8. | ipr-mus LD50:505 mg/kg | TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. 29 (1982),400. | ||
9. | ivn-mus LDLo:500 mg/kg | 85ERAY Antibiotics: Origin, Nature, and Properties. 3 (1978),1740. |
EPA Genetic Toxicology Program.
A poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Mycophenolic acid (CAS NO.24280-93-1):
Hazard Codes: Xn
Risk Statements: 22-61-40
R22:Harmful if swallowed.
R61:May cause harm to the unborn child.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 53-45-36/37
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
RIDADR: 2811
WGK Germany: 3
RTECS: MP8050000
F: 10
HazardClass: 6.1(b)
PackingGroup: III
Mycophenolic acid , with CAS number of 24280-93-1, can be called 6-(1,3-Dihydro-7-hydroxy-5-methoxy-4-methyl-1-oxoisobenzofuran-6-yl)-4-methyl-4-hexanoic acid ; 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid . It is a white to off-white powder. Mycophenolic acid (CAS NO.24280-93-1) is an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleot.