Name: Vorinostat
SKU: 149647-78-9

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Basic Information

Molecular Structure:
CAS No.:	149647-78-9
Name:	Vorinostat
Article Data:	39

Formula:	C₁₄H₂₀N₂O₃
Molecular Weight:	264.324
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;
EINECS:	682-505-1
Density:	1.174 g/cm³
Melting Point:	161-162 °C
Appearance:	white crystalline solid
Hazard Symbols:	T
Risk Codes:	61-68
Safety:	53-36/37-45
PSA:	78.43000
LogP:	2.93500

Synthetic route

: 162853-41-0
7-phenylcarbamoyl heptanoic acid methyl ester

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C17H23NO5

: 149647-78-9
vorinostat

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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Chemistry

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

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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