Product Name

  • Name

    Seratrodast

  • EINECS 692-169-8
  • CAS No. 112665-43-7
  • Article Data8
  • CAS DataBase
  • Density 1.14 g/cm3
  • Solubility
  • Melting Point 118-120 °C
  • Formula C22H26O4
  • Boiling Point 522.3 °C at 760 mmHg
  • Molecular Weight 354.446
  • Flash Point 283.8 °C
  • Transport Information
  • Appearance pale orange solid
  • Safety
  • Risk Codes R36/37/38
  • Molecular Structure Molecular Structure of 112665-43-7 (Seratrodast)
  • Hazard Symbols Xi
  • Synonyms Benzeneheptanoicacid, z-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-,(?à)-;7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid;A 73001;AA 2414;ABT 001;Abbott 73001;Bronica;
  • PSA 71.44000
  • LogP 4.61000

Synthetic route

1,4-dimethoxy-2,3,5-trimethyl-benzene
4537-09-1

1,4-dimethoxy-2,3,5-trimethyl-benzene

C13H19NO2

C13H19NO2

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Stage #1: 1,4-dimethoxy-2,3,5-trimethyl-benzene; C13H19NO2 With sodium nitrate; aluminum isopropoxide at 47℃; for 2h;
Stage #2: With dipotassium peroxodisulfate; sodium sulfate at 55℃; for 0.833333h;
Stage #3: With niobium(V) oxide for 3.6h; Temperature;		99.2%
potassium nitrosodisulfonate (Fremy's salt)

potassium nitrosodisulfonate (Fremy's salt)

7-(2-hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid
148989-82-6

7-(2-hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
With ammonium hydroxide In water; acetonitrile94.1%
Trimethylhydroquinone
700-13-0

Trimethylhydroquinone

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

7-hydroxy-7-phenylheptanoic acid
103187-18-4

7-hydroxy-7-phenylheptanoic acid

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
With iron(III) chloride In tetrahydrofuran; water; toluene73%
...Expand
2,3,5-Trimethyl-1,4-benzoquinone
935-92-2

2,3,5-Trimethyl-1,4-benzoquinone

phenyl-2-oxocanone

phenyl-2-oxocanone

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Stage #1: 2,3,5-Trimethyl-1,4-benzoquinone; phenyl-2-oxocanone With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 0.5h;
Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) at 40℃; for 6h;		46%
7-(2,5-Dihydroxy-3,4,6-trimethyl-phenyl)-7-phenyl-heptanoic acid
148989-73-5

7-(2,5-Dihydroxy-3,4,6-trimethyl-phenyl)-7-phenyl-heptanoic acid

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
With iron(III) chloride In tetrahydrofuran for 0.5h; Ambient temperature; Yield given;
With iron(III) chloride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;
ethyl 6-(chloroformyl)hexanoate
14794-32-2

ethyl 6-(chloroformyl)hexanoate

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: AlCl3 / 2 h / 90 °C
2: NaBH4 / methanol / 0.5 h / 0 °C
3: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C
4: boron trifluoride etherate / toluene / 2 h / 60 °C
5: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
7-ethoxy-7-oxoheptanoic acid
33018-91-6

7-ethoxy-7-oxoheptanoic acid

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / SOCl2 / CH2Cl2 / 2 h / 50 °C
2: AlCl3 / 2 h / 90 °C
3: NaBH4 / methanol / 0.5 h / 0 °C
4: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C
5: boron trifluoride etherate / toluene / 2 h / 60 °C
6: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
ethyl 7-oxo-7-phenylheptanoate
112665-41-5

ethyl 7-oxo-7-phenylheptanoate

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaBH4 / methanol / 0.5 h / 0 °C
2: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C
3: boron trifluoride etherate / toluene / 2 h / 60 °C
4: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
7-hydroxy-7-phenyl-heptanoic acid ethyl ester
112665-42-6

7-hydroxy-7-phenyl-heptanoic acid ethyl ester

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C
2: boron trifluoride etherate / toluene / 2 h / 60 °C
3: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
7-hydroxy-7-phenylheptanoic acid
103187-18-4

7-hydroxy-7-phenylheptanoic acid

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trifluoride etherate / toluene / 2 h / 60 °C
2: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
bromobenzene
108-86-1

bromobenzene

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / Sealed tube; Inert atmosphere; Reflux
1.2: 20 °C / Sealed tube; Inert atmosphere
1.3: Sealed tube; Inert atmosphere; Reflux; Dean-Stark
2.1: borane-THF / tetrahydrofuran / 2.5 h / 20 °C / Sealed tube; Inert atmosphere
2.2: 4 h / 20 °C / Sealed tube; Inert atmosphere
3.1: pyridinium chlorochromate / dichloromethane / 24 h / 0 - 20 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 35 °C / Inert atmosphere; Sealed tube
5.1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 0.5 h / 20 °C
5.2: 6 h / 40 °C
View Scheme
cycloheptanone
502-42-1

cycloheptanone

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / Sealed tube; Inert atmosphere; Reflux
1.2: 20 °C / Sealed tube; Inert atmosphere
1.3: Sealed tube; Inert atmosphere; Reflux; Dean-Stark
2.1: borane-THF / tetrahydrofuran / 2.5 h / 20 °C / Sealed tube; Inert atmosphere
2.2: 4 h / 20 °C / Sealed tube; Inert atmosphere
3.1: pyridinium chlorochromate / dichloromethane / 24 h / 0 - 20 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 35 °C / Inert atmosphere; Sealed tube
5.1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 0.5 h / 20 °C
5.2: 6 h / 40 °C
View Scheme
1-Phenylcycloheptene
25308-75-2, 71340-35-7, 152016-48-3

1-Phenylcycloheptene

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: borane-THF / tetrahydrofuran / 2.5 h / 20 °C / Sealed tube; Inert atmosphere
1.2: 4 h / 20 °C / Sealed tube; Inert atmosphere
2.1: pyridinium chlorochromate / dichloromethane / 24 h / 0 - 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 35 °C / Inert atmosphere; Sealed tube
4.1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 0.5 h / 20 °C
4.2: 6 h / 40 °C
View Scheme
2-phenylcycloheptan-1-ol
92035-59-1

2-phenylcycloheptan-1-ol

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridinium chlorochromate / dichloromethane / 24 h / 0 - 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 35 °C / Inert atmosphere; Sealed tube
3.1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 0.5 h / 20 °C
3.2: 6 h / 40 °C
View Scheme
2-phenylcycloheptanone
14996-78-2

2-phenylcycloheptanone

seratrodast
112665-43-7

seratrodast

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 35 °C / Inert atmosphere; Sealed tube
2.1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 0.5 h / 20 °C
2.2: 6 h / 40 °C
View Scheme
2-(N-tert-butoxycarbonylamino)ethanol
26690-80-2

2-(N-tert-butoxycarbonylamino)ethanol

seratrodast
112665-43-7

seratrodast

C29H39NO6

C29H39NO6

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;100%
methanol
67-56-1

methanol

seratrodast
112665-43-7

seratrodast

6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzoquinone

6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzoquinone

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 2h;98%
4-nitro-phenol
100-02-7

4-nitro-phenol

seratrodast
112665-43-7

seratrodast

p-nitrophenyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoate
112665-40-4

p-nitrophenyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane 1) 0 deg C, 30 min, 2) room temperature, 1 h;91%
seratrodast
112665-43-7

seratrodast

7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanamide

7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / dicyclohexyl carbodiimide / CH2Cl2 / 1) 0 deg C, 30 min, 2) room temperature, 1 h
2: 87 percent / aq. conc. ammonia / tetrahydrofuran / 4 h / Ambient temperature
View Scheme
seratrodast
112665-43-7

seratrodast

7-Phenyl-7-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-heptanoic acid isopropylamide

7-Phenyl-7-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-heptanoic acid isopropylamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / dicyclohexyl carbodiimide / CH2Cl2 / 1) 0 deg C, 30 min, 2) room temperature, 1 h
2: 81 percent / tetrahydrofuran / Ambient temperature
View Scheme
seratrodast
112665-43-7

seratrodast

7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycine

7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / dicyclohexyl carbodiimide / CH2Cl2 / 1) 0 deg C, 30 min, 2) room temperature, 1 h
View Scheme
seratrodast
112665-43-7

seratrodast

7-Phenyl-7-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-heptanoic acid (1-phenyl-ethyl)-amide

7-Phenyl-7-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-heptanoic acid (1-phenyl-ethyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / dicyclohexyl carbodiimide / CH2Cl2 / 1) 0 deg C, 30 min, 2) room temperature, 1 h
2: 85 percent / tetrahydrofuran / Ambient temperature
View Scheme
4-(N-imidazolyl)aniline
2221-00-3

4-(N-imidazolyl)aniline

seratrodast
112665-43-7

seratrodast

N-[4-(imidazol-1-yl)phenyl]-7-phenyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)heptanamide

N-[4-(imidazol-1-yl)phenyl]-7-phenyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)heptanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h;
diazomethane
186581-53-3, 908094-01-9

diazomethane

seratrodast
112665-43-7

seratrodast

6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzoquinone

6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzoquinone

seratrodast
112665-43-7

seratrodast

seratrodast aminoethyl ester

seratrodast aminoethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap / dichloromethane; N,N-dimethyl-formamide / 20 °C / Cooling with ice
2: hydrogenchloride / dichloromethane; ethyl acetate / 2 h / 20 °C / Cooling with ice
View Scheme

Seratrodast Chemical Properties

Molecular structure of Seratrodast (CAS NO.112665-43-7) is:

Product Name: Seratrodast
CAS Registry Number: 112665-43-7
IUPAC Name: 7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
Molecular Weight: 354.43944 [g/mol]
Molecular Formula: C22H26O4
XLogP3-AA: 4.4
H-Bond Donor: 1
H-Bond Acceptor: 4
Melting point: 118-120 °C
Density: 1.14 g/cm3  
Flash Point: 283.8 °C
Enthalpy of Vaporization: 83.77 kJ/mol
Boiling Point: 522.3 °C at 760 mmHg
Vapour Pressure: 9.74E-12 mmHg at 25°C
Surface Tension: 45.2 dyne/cm 
Other Registry Number: 103186-19-2
Product Categories: API;Heterocyclic Compounds;Intermediates & Fine Chemicals;Pharmaceuticals

Seratrodast Uses

 Seratrodast (CAS NO.112665-43-7) is a thromboxane receptor antagonist used primarily in the treatment of asthma.

Seratrodast Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 394, 1996.
mouse LD50 intraperitoneal 1100mg/kg (1100mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse LD50 oral 1520mg/kg (1520mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 intraperitoneal 1350mg/kg (1350mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 oral 3750mg/kg (3750mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.

Seratrodast Specification

 Seratrodast , its cas register number is 112665-43-7. It also can be called (+-)-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid ; (+-)-2,4,5-Trimethyl-3,6-dioxo-zeta-phenyl-1,4-cyclohexadiene-1-heptanoic acid ; Benzeneheptanoic acid, zeta-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-, (+-)- .It is a pale orange solid.

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