5090-54-0

Basic information

• Product Name: VALERANONE
• Synonyms: VALERANONE;(7R)-4a,8a-dimethyl-7-propan-2-yl-decalin-1-one;(-)-Jatamansone;(4aS)-3,4,4a,5,6,7,8,8a-Octahydro-4aα,8aα-dimethyl-7β-isopropylnaphthalen-1(2H)-one
• CAS NO: 5090-54-0
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.36634
• Mol File: 5090-54-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 287.9°Cat760mmHg
• Flash Point: 120.4°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.00242mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: VALERANONE(CAS DataBase Reference)
• NIST Chemistry Reference: VALERANONE(5090-54-0)
• EPA Substance Registry System: VALERANONE(5090-54-0)

Safety Data

• Hazardous Substances Data: 5090-54-0(Hazardous Substances Data)

Usage

General Description

Valeranone is a chemical compound known for its sedative and anxiolytic properties. It is commonly found in the roots of valerian plants, which have long been used in traditional medicine to promote relaxation and reduce anxiety. Valeranone is believed to work by increasing the levels of gamma-aminobutyric acid (GABA) in the brain, leading to a calming effect on the central nervous system. As a result, it is commonly used as a natural remedy for insomnia, restlessness, and stress. Research has also suggested that valeranone may have potential in the treatment of neurodegenerative diseases, due to its antioxidant and neuroprotective properties. However, more studies are needed to fully understand its mechanisms and potential therapeutic applications.

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

• 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 
• 177532-95-5 (1S,3R,6R,9S)-3-isopropyl-1,6,9-trimethylbicyclo[4.3.0]nonan-8-one 

Downstream Products

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

Relevant articles and documents

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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.

STRUCTURE OF KANOKONOL.

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