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Basic Information

Molecular Structure:
CAS No.:	24280-93-1
Name:	Mycophenolic acid
Article Data:	27

Formula:	C₁₇H₂₀O₆
Molecular Weight:	320.342
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;
EINECS:	246-119-3
Density:	1.29 g/cm³
Melting Point:	141 °C
Boiling Point:	611.6 °C at 760 mmHg
Flash Point:	225.8 °C
Solubility:	Almost insoluble in cold water. Soluble in alcohol
Appearance:	White to off-white powder
Hazard Symbols:	Xn
Risk Codes:	22-61-40
Safety:	53-45-36/37
PSA:	93.06000
LogP:	2.73320

Synthetic route

: 32483-51-5
ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate

: 24280-93-1
mycophenolic acid

Conditions

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%

: 31858-66-9
methyl mycophenolate

: 24280-93-1
mycophenolic acid

Conditions

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%

: 31327-49-8
7-hydroxy-6-[(E)-6-hydroxy-3-methylhex-2-enyl]-5-methoxy-4-methyl-3H-2-benzofuran-1-one

: 24280-93-1
mycophenolic acid

Conditions

Conditions	Yield
With jones reagent In acetone at -30℃; for 5h;	61%

: 50-99-7
D-glucose

: 24280-93-1
mycophenolic acid

Conditions

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;

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;

: 38877-93-9
7-O-Methylmycophenolic acid

: 24280-93-1
mycophenolic acid

Conditions

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

: 60435-90-7
5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide

: 24280-93-1
mycophenolic acid

Conditions

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

: 545392-47-0
(E)-6-(4,6-Dimethoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-4-methyl-hex-4-enal

: 24280-93-1
mycophenolic acid

Conditions

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

: 207398-37-6
6-((E)-3,7-Dimethyl-octa-2,6-dienyl)-5,7-dimethoxy-4-methyl-3H-isobenzofuran-1-one

: 24280-93-1
mycophenolic acid

Conditions

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

: 207398-36-5
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-2,4-dimethoxy-5-methyl-benzoic acid methyl ester

: 24280-93-1
mycophenolic acid

Conditions

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

: 207402-09-3
3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propionyloxymethyl)-5-formyl-2,4-dimethoxy-benzoic acid methyl ester

: 24280-93-1
mycophenolic acid

Conditions

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

Raw Materials

50-99-7

Downstream Products

527-55-9

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Chemistry

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 Å²EINECS: 246-119-3
Density: 1.29 g/cm³
Melting Point: 141^oC
Boiling Point: 611.6^oC at 760 mmHg
Flash Point: 225.8^oC
Solubility: Almost insoluble in cold water. Soluble in alcohol
Appearance: White to off-white powder
Properties: Needles from hot water.
Storage temp: 2-8^oC
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

Toxicity Data With Reference

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.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

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: Harmful 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

Specification

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.