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Vorinostat
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Name

Vorinostat

 EINECS 682-505-1
CAS No. 149647-78-9 Density 1.174 g/cm3
PSA 78.43000 LogP 2.93500
Solubility N/A Melting Point 161-162 °C
Formula C14H20N2O3 Boiling Point N/A
Molecular Weight 264.324 Flash Point N/A
Transport Information N/A Appearance white crystalline solid
Safety 53-36/37-45 Risk Codes 61-68
Molecular Structure Molecular Structure of 149647-78-9 (Vorinostat) Hazard Symbols T
Synonyms

Octanediamide,N-hydroxy-N'-phenyl- (9CI);N-Hydroxy-N'-phenyloctanediamide;SAHA;Suberoylanilide hydroxamic acid;Zolinza;CCRIS 8456;M344;SAHA cpd;Suberanilohydroxamic acid;UNII-58IFB293JI;

Article Data 39

Vorinostat Synthetic route

162853-41-0

7-phenylcarbamoyl heptanoic acid methyl ester

149647-78-9

vorinostat

Conditions
ConditionsYield
Stage #1: 7-phenylcarbamoyl heptanoic acid methyl ester With hydroxylamine hydrochloride; sodium methylate In methanol; water for 16.1667h;
Stage #2: With water; acetic acid In methanol for 0.166667h; pH=8.7 - 12.02;		95.6%
With hydroxylamine hydrochloride; sodium methylate In methanol for 16.1667h;95.6%
Stage #1: 7-phenylcarbamoyl heptanoic acid methyl ester With hydroxylamine hydrochloride; sodium methylate In methanol for 16.3333h;
Stage #2: With sodium methylate In methanol; water for 0.166667h; pH=12.01 - 12.02;
Stage #3: With acetic acid In methanol; water pH=8.70 - 8.98; Product distribution / selectivity;		95.6%

C21H24N2O3

149647-78-9

vorinostat

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen; trifluoroacetic acid In methanol at 20℃; for 2h;91%
6998-10-3

N-phenylhexanamide

149647-78-9

vorinostat

Conditions
ConditionsYield
With hydroxylamine hydrochloride In N,N-dimethyl-formamide at 40℃; for 1h; Reagent/catalyst;88.5%
149647-86-9

8-(hydroxyamino)-8-oxooctanoic acid

62-53-3

aniline

149647-78-9

vorinostat

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; potassium hydroxide In ethanol at 50℃; for 0.5h;82.4%
With dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole In tetrahydrofuran
149648-52-2

suberanilic acid

149647-78-9

vorinostat

Conditions
ConditionsYield
With C36H24B4N2O3; hydroxylamine hydrochloride; triethylamine In toluene at 80℃; for 14h; Molecular sieve;82%
Stage #1: suberanilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h;
Stage #2: With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;		75%
Stage #1: suberanilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h;
Stage #2: With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;		75%
162853-41-0

7-phenylcarbamoyl heptanoic acid methyl ester

A

149648-52-2

suberanilic acid

B

149647-78-9

vorinostat

Conditions
ConditionsYield
With water; hydroxylamine; sodium methylate In methanol at 90℃;A 15%
B 80%

C17H23NO5

149647-78-9

vorinostat

Conditions
ConditionsYield
With hydroxylamine In methanol
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20℃; for 0.25h;
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
3: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry
4: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C
View Scheme
With hydroxylamine hydrochloride In tetrahydrofuran; methanol at 20℃; for 1.5h;
With hydroxylamine hydrochloride; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 0.5h;0.14 g
3946-32-5

suberic acid monomethyl ester

149647-78-9

vorinostat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88.7 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 1.5 h / 20 °C
2: 90 percent / hydroxylamine; KOH / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 3 h / Reflux
2: triethylamine / dichloromethane / 1.5 h / 20 °C
3: hydroxylamine hydrochloride; sodium methylate / methanol / 0.67 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-hydroxy-1H-benzotriazole hydrate / N,N-dimethyl-formamide
2: potassium hydroxide; hydroxylamine hydrochloride / methanol
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane / 20 °C / Cooling with ice
2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C
3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 °C / Cooling with ice
3.2: 20 °C
4.1: dihydrogen peroxide / aq. phosphate buffer / 4 h / 37 °C / pH 7.4
View Scheme
62-53-3

aniline

[(Xantphos)2Pd(3-methyl-1-butenyl]OTf

[(Xantphos)2Pd(3-methyl-1-butenyl]OTf

149647-78-9

vorinostat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88.7 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 1.5 h / 20 °C
2: 90 percent / hydroxylamine; KOH / methanol / 1 h / 20 °C
View Scheme
505-48-6

octane-1,8-dioic acid

149647-78-9

vorinostat

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / Ac2O / 1 h / Heating
2: 94 percent / tetrahydrofuran / 0.5 h / 20 °C
3: Et3N / tetrahydrofuran / 0.17 h
4: NH2OH / methanol
View Scheme
Multi-step reaction with 6 steps
1.1: 0.17 h / 150 - 180 °C
1.2: 0.33 h / 20 °C
2.1: triethylamine / tetrahydrofuran / 0.25 h / -10 °C
3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
5.1: Benzoylformic acid / Petroleum ether / 48 h / 20 °C / Irradiation; Green chemistry
6.1: hydroxylamine hydrochloride; triethylamine / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 0.17 h / 185 - 190 °C / Sealed tube
2: Dowex50W-X2 acid resin / 22 h / Reflux
3: methanol; hydroxylamine hydrochloride; sodium
View Scheme
Multi-step reaction with 3 steps
1.1: 0.33 h / 175 - 190 °C
1.2: 0.33 h
2.1: 18 h / Heating / reflux
3.1: hydroxylamine hydrochloride; sodium methylate / methanol
View Scheme
Multi-step reaction with 3 steps
1.1: acetic anhydride
2.1: tetrahydrofuran
3.1: triethylamine; chloroformic acid ethyl ester / 0 °C
3.2: 20 °C
View Scheme

Vorinostat Chemical Properties

IUPAC Name: N'-Hydroxy-N-phenyloctanediamide
Synonyms of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): Vorinostat [USAN] ; CCRIS 8456 ; M344 ; N-Hydroxy-N'-phenyloctanediamide ; SAHA ; SAHA cpd ; Suberanilohydroxamic acid ; UNII-58IFB293JI ; Vorinostat ; Zolinza ; Suberoylanilide hydroxamic acid
CAS NO: 149647-78-9
Classification Code: Analgesics ; Analgesics, Non-Narcotic ; Anti-Inflammatory Agents ; Anti-Inflammatory Agents, Non-Steroidal ; Anticarcinogenic Agents ; Antineoplastic Agents ; Antirheumatic Agents ; Antitumor agent ; Enzyme Inhibitors ; Histone deacetylase inhibitor ; Peripheral Nervous System Agents ; Protective Agents ; Sensory System Agents
Molecular Formula of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): C14H20N2O3
Molecular Weight: 264.3202 
Molecular Structure:

Melting Point: 161-162°C 
Polar Surface Area: 49.85 Å2
Index of Refraction: 1.566
Molar Refractivity: 73.48 cm3
Molar Volume: 224.9 cm3
Surface Tension: 50.3 dyne/cm
Density of Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9): 1.174 g/cm3

Vorinostat Uses

 Octanediamide,N1-hydroxy-N8-phenyl- (CAS NO.149647-78-9) is used as a powerful, selective, cell histone deacetylase inhibitors permeable (the HDAC). Display anti-angiogenic and vascular endothelial growth factor interference signal activity in human umbilical vein endothelial cells (endothelial cells).

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