5090-54-0

Usage

Uses

Used in Pharmaceutical Industry:
Valeranone is used as a natural sedative and anxiolytic agent for promoting relaxation and reducing anxiety. It is particularly effective in treating insomnia, restlessness, and stress due to its ability to increase GABA levels in the brain, leading to a calming effect on the central nervous system.
Used in Neurodegenerative Disease Treatment:
Valeranone is used as a potential therapeutic agent in the treatment of neurodegenerative diseases. Its antioxidant and neuroprotective properties suggest that it may help protect the brain from oxidative stress and neuronal damage, although more research is needed to fully understand its mechanisms and potential applications in this area.

InChI:InChI=1/C15H26O/c1-11(2)12-7-9-14(3)8-5-6-13(16)15(14,4)10-12/h11-12H,5-10H2,1-4H3/t12-,14?,15?/m1/s1

Synthetic route

(1R,6R,9R)-1,6-dimethyl-9-isopropylbicyclo[4.4.0]dec-3-en-2-one (177533-01-6) → valeranone (5090-54-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 12h;	80%
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 12h;	80%

Deoxyfauronol-aethylenketal (2212-97-7, 106707-55-5) → valeranone (5090-54-0)

Conditions	Yield
With hydrogenchloride

8,8-Aethylendioxy-(2R)-isopropyl-(4aR)-hydroxymethyl-(8aR)-methyl-dekalin (4893-79-2, 98573-74-1) → valeranone (5090-54-0)

Conditions	Yield
(i) CrO3, Py, (ii) N2H4*H2O, KOH, (iii) aq. AcOH; Multistep reaction;

(1aR,4aS,7R,8aS)-7-Isopropyl-1a-methoxy-4a-methyl-decahydro-cyclopropa[d]naphthalene (16735-11-8, 66510-89-2) → valeranone (5090-54-0)

Conditions	Yield
With hydrogenchloride

(1S,3aR,6R,7aS)-2-Iodo-6-isopropyl-1,3a,7a-trimethyl-octahydro-indene (823203-43-6) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 0.5 h / 160 °C 1.2: ozone / methanol; CH2Cl2 / -78 °C 1.3: triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 2.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 3.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1S,3R,6R,9S)-3-isopropyl-1,6,9-trimethylbicyclo[4.3.0]nonan-8-ol (823203-42-5) → valeranone (5090-54-0)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 76 percent / iodine; triphenylphosphine; imidazole / benzene / 2 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 0.5 h / 160 °C 2.2: ozone / methanol; CH2Cl2 / -78 °C 2.3: triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 3.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 4.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1R,2R,4R)-1,2,-dimethyl-2-(1-hydroxyethyl)-4-isopropylcyclohexaneethanol (177532-97-7) → valeranone (5090-54-0)

Conditions

Yield

Multi-step reaction with 6 steps 1: 65 percent / imidazole / CH2Cl2 / 1 h / 0 °C 2: 82 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 3: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 4: 72 percent / PCC; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 5: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 6: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1S,3R,6R,9S)-3-isopropenyl-1,6,9-trimethylbicyclo[4.3.0]nonan-8-one (177532-94-4) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 99 percent / H2 / Pd/C / methanol / 12 h 2.1: 96 percent / NaBH4 / methanol / 0.25 h / cooling 3.1: 76 percent / iodine; triphenylphosphine; imidazole / benzene / 2 h / 20 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 0.5 h / 160 °C 4.2: ozone / methanol; CH2Cl2 / -78 °C 4.3: triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 5.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 6.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme
Multi-step reaction with 4 steps 1: 98 percent / H2 / 10percent Pd/C / methanol / 6 h 2: 1.) NaBH4, 2.) PPh3, iodine, imidazole / 1.) MeOH, 0 deg C, 15 min, 2.) C6H6, room temperature 2 h 4: 80 percent / H2 / 10percent Pd/C / methanol / 12 h View Scheme

(1S,3R,6R,9S)-3-isopropyl-1,6,9-trimethylbicyclo[4.3.0]nonan-8-one (177532-95-5) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 96 percent / NaBH4 / methanol / 0.25 h / cooling 2.1: 76 percent / iodine; triphenylphosphine; imidazole / benzene / 2 h / 20 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 0.5 h / 160 °C 3.2: ozone / methanol; CH2Cl2 / -78 °C 3.3: triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 4.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 5.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: 1.) NaBH4, 2.) PPh3, iodine, imidazole / 1.) MeOH, 0 deg C, 15 min, 2.) C6H6, room temperature 2 h 3: 80 percent / H2 / 10percent Pd/C / methanol / 12 h View Scheme

(1R,2S,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-4-one (177532-96-6) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 7 steps 1: 98 percent / lithium aluminium hydride / diethyl ether / 0.5 h / 20 °C 2: 65 percent / imidazole / CH2Cl2 / 1 h / 0 °C 3: 82 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 4: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 5: 72 percent / PCC; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 6: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 7: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme
Multi-step reaction with 6 steps 1.1: 87 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C 2.1: 57 percent / tetrahydrofuran / 1 h / 40 °C 3.1: 80 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 4.1: ozone / methanol; CH2Cl2 / -75 °C 4.2: 75 percent / triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 5.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 6.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

2-[(1R,2R,4R)-2-acetyl-4-isopropyl-1,2-dimethylcyclohexyl]acetaldehyde (261957-25-9) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 2: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

1-[(1R,2R,5R)-(2-allyl-5-isopropyl-1,2-dimethylcyclohexyl)]ethanone (261957-31-7) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ozone / methanol; CH2Cl2 / -75 °C 1.2: 75 percent / triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 2.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 3.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1S)-1-[(1R,2R,5R)-(2-allyl-5-isopropyl-1,2-dimethylcyclohexyl)]ethanol (261957-30-6) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 80 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 2.1: ozone / methanol; CH2Cl2 / -75 °C 2.2: 75 percent / triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 3.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 4.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1R,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-2-ol (261957-28-2) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / PCC; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 2: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 3: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1R,2R,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-4-ol (261957-29-3) → valeranone (5090-54-0)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 57 percent / tetrahydrofuran / 1 h / 40 °C 2.1: 80 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 3.1: ozone / methanol; CH2Cl2 / -75 °C 3.2: 75 percent / triphenylphosphine / methanol; CH2Cl2 / 8 h / 20 °C 4.1: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 5.1: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

1-[(1R,2R,5R)-2-(2-tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]-1-ethanone (261957-27-1) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 2: 72 percent / PCC; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 3: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 4: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(1S)-1-[(1R,2R,5R)-2-(tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]ethanol (261957-26-0) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 2: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 3: 72 percent / PCC; sodium acetate / CH2Cl2 / 0.5 h / 20 °C 4: 76 percent / KOH / tetrahydrofuran; methanol; H2O / 8 h / 20 °C 5: 80 percent / H2 / Pd/C / methanol / 12 h / 760 Torr View Scheme

(3aR,6R,7aS)-2-Iodo-6-isopropyl-1,3a,7a-trimethyl-octahydro-indene → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: 80 percent / H2 / 10percent Pd/C / methanol / 12 h View Scheme

5ξ-Hydroxy-7β-isopropyl-4ξ-methoxy-10α-methyl-3-decalon (16840-48-5) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: KOH 2: LiAlH4 3: I2, Zn-Cu 4: CrO3, H2SO4 5: N2H4, diethylene glycol, KOH 6: aq. HCl View Scheme

7β-Isopropyl-4β-methoxy-10α-methyl-4α,5α-methylen-3α-decalol (16735-09-4, 66510-87-0) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: CrO3, H2SO4 2: N2H4, diethylene glycol, KOH 3: aq. HCl View Scheme

7β-Isopropyl-4-methoxy-10α-methyl-4-octalin-3α-ol (66510-86-9) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: I2, Zn-Cu 2: CrO3, H2SO4 3: N2H4, diethylene glycol, KOH 4: aq. HCl View Scheme

(1aR,4aR,7R,8aS)-7-Isopropyl-1a-methoxy-4a-methyl-octahydro-cyclopropa[d]naphthalen-2-one (16735-10-7, 66510-88-1) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N2H4, diethylene glycol, KOH 2: aq. HCl View Scheme

7β-Isopropyl-4-methoxy-10α-methyl-4-octalin-3-on (66334-13-2) → valeranone (5090-54-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: LiAlH4 2: I2, Zn-Cu 3: CrO3, H2SO4 4: N2H4, diethylene glycol, KOH 5: aq. HCl View Scheme

valeranone (5090-54-0) → (4aS)-7t-Isopropyl-4a,8a-dimethyl-(4ar,8ac)-decahydro-[1c]naphthol (4893-70-3, 4893-71-4, 17408-73-0, 114127-46-7, 114127-47-8)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride

valeranone (5090-54-0) → (4aR)-2ξ-bromo-7t-isopropyl-4a,8a-dimethyl-(4ar,8ac)-octahydro-naphthalen-1-one (2658-90-4, 18866-65-4)

Conditions	Yield
With bromine
With bromine In acetic acid

diazomethane (186581-53-3, 908094-01-9) + valeranone (5090-54-0) → Trisnorphotovaleronsaeuremethylester

Conditions	Yield
Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + valeranone (5090-54-0) → Bisnorphotovaleronsaeuremethylester

Conditions	Yield
Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + valeranone (5090-54-0) → Norphotovaleronsaeuremethylester

Conditions	Yield
Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + valeranone (5090-54-0) → Photovaleronsaeuremethylester

Conditions	Yield
(i) (UV-irradiation), (ii) /BRN= 102415/; Multistep reaction;

valeranone (5090-54-0) → (1R,3R,6S)-3-Isopropyl-1,6-dimethylbicyclo[4.4.0]decane (5050-72-6)

Conditions	Yield
With potassium hydroxide; hydrazine at 180 - 190℃;
With sodium; hydrazine hydrate
Multi-step reaction with 2 steps 1: (i) LiAlH4, (ii) phthalic anhydride 2: H2 / PtO2 View Scheme

valeranone (5090-54-0) → (4aS)-7t-Isopropyl-4a,8a-dimethyl-(4ar,8ac)-decahydro-[1c]naphthol (4893-70-3, 4893-71-4, 17408-73-0, 114127-46-7, 114127-47-8) + 4-epi-Valeranol (4893-70-3, 4893-71-4, 17408-73-0, 114127-46-7, 114127-47-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Heating;

valeranone (5090-54-0) → 4-epi-Valeranol (4893-70-3, 4893-71-4, 17408-73-0, 114127-46-7, 114127-47-8)

Conditions	Yield
With sodium ethanolate In ethanol

valeranone (5090-54-0) → (4aR)-2,2-dibromo-7t-isopropyl-4a,8a-dimethyl-(4ar,8ac)-octahydro-naphthalen-1-one

Conditions	Yield
With bromine In acetic acid

valeranone (5090-54-0) → Jatamansen (177186-97-9)

Conditions	Yield
(i) LiAlH4, (ii) phthalic anhydride; Multistep reaction;

valeranone (5090-54-0) → Trisnorphotovaleronsaeure

Conditions	Yield
Multistep reaction;

valeranone (5090-54-0) → Bisnorphotovaleronsaeure

Conditions	Yield
Multistep reaction;

valeranone (5090-54-0) → Norphotovaleronsaeure

Conditions	Yield
Multistep reaction;

valeranone (5090-54-0) → Photovaleronsaeure

Conditions	Yield
In acetic acid Irradiation;

valeranone (5090-54-0) + benzaldehyde (100-52-7) → (4aR)-2-((Ξ)-benzylidene)-7t-isopropyl-4a,8a-dimethyl-(4ar,8ac)-octahydro-naphthalen-1-one (100270-35-7)

Conditions	Yield
With sodium ethanolate
(i) HCl, (ii) NaOAc; Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + valeranone (5090-54-0) → Hydroxyvaleranosaeuremethylester (5487-10-5, 93190-80-8)

Conditions	Yield
(i) PhCO3H, (ii) (hydrolysis), (iii) /BRN= 102415/; Multistep reaction;

Upstream product

• 4893-79-2 8,8-Aethylendioxy-(2R)-isopropyl-(4aR)-hydroxymethyl-(8aR)-methyl-dekalin 
• 66334-13-2 7β-Isopropyl-4-methoxy-10α-methyl-4-octalin-3-on 
• 16735-10-7 (1aR,4aR,7R,8aS)-7-Isopropyl-1a-methoxy-4a-methyl-octahydro-cyclopropa[d]naphthalen-2-one 
• 66510-86-9 7β-Isopropyl-4-methoxy-10α-methyl-4-octalin-3α-ol 
• 16735-09-4 7β-Isopropyl-4β-methoxy-10α-methyl-4α,5α-methylen-3α-decalol 
• 16840-48-5 5ξ-Hydroxy-7β-isopropyl-4ξ-methoxy-10α-methyl-3-decalon 
• 261957-26-0 (1S)-1-[(1R,2R,5R)-2-(tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]ethanol 
• 261957-27-1 1-[(1R,2R,5R)-2-(2-tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]-1-ethanone 
• 261957-29-3 (1R,2R,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-4-ol 
• 261957-28-2 (1R,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-2-ol 
• 261957-30-6 (1S)-1-[(1R,2R,5R)-(2-allyl-5-isopropyl-1,2-dimethylcyclohexyl)]ethanol 
• 261957-31-7 1-[(1R,2R,5R)-(2-allyl-5-isopropyl-1,2-dimethylcyclohexyl)]ethanone 
• 261957-25-9 2-[(1R,2R,4R)-2-acetyl-4-isopropyl-1,2-dimethylcyclohexyl]acetaldehyde 
• 177532-96-6 (1R,2S,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-4-one 

Downstream Products

• 92791-46-3 (1R)-2c-(2-carboxy-ethyl)-5c-isopropyl-1,2t-dimethyl-cyclohexane-r-carboxylic acid 

Relevant academic research and scientific papers

Enantiospecific total syntheses of (-)-valeranone

Two convenient methodologies have been described for the enantiospecific synthesis of (-)-valeranone 1. The hydrindanone 12, obtained from the readily and abundantly available monoterpene (R)-carvone, has been converted into the ketoaldehyde 16 via the alkene 15b. In another direction the lactone 18, obtained from the hydrindanone 12, has been elaborated into the ketoaldehyde 16 employing two methodologies. Intramolecular aldol condensation followed by hydrogenation transformed the ketoaldehyde 16 into (-)-valeranone 1.

Stereo- and enantiospecific total synthesis of (-)-valeranone

Stereo- and enantiospecific total synthesis of the irregular sesquiterpene, valeranone, starting from S-6-methylcarvone employing a hydrindanone to decalone ring expansion methodology, is described.