491-07-6

Basic information

• Product Name: ISOMENTHONE
• Synonyms: (Z)-5-Methyl-2-(1-methylethyl)-cyclohexanone;rel-(2R,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone;cis-p-Menthone;alpha-Isomenthone;(±)-cis-p-menthan-3-one;(z)-cyclohexanon;(z)-p-menthan-3-on;5-methyl-2-(1-methylethyl)-,cis-Cyclohexanone
• CAS NO: 491-07-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 207-727-4
• Mol File: 491-07-6.mol
• Article Data: 53

Chemical Properties

• Melting Point: -35 °C
• Boiling Point: 217.64°C (rough estimate)
• Flash Point: 72.8°C
• Appearance: /
• Density: 0.8389 (rough estimate)
• Refractive Index: 1.4666 (estimate)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: ISOMENTHONE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOMENTHONE(491-07-6)
• EPA Substance Registry System: ISOMENTHONE(491-07-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 491-07-6(Hazardous Substances Data)

Usage

Description

Synthesis: By hydrogenation of pipertone.

Chemical Properties

dl-Isomenthone has a peppermint odor

Occurrence

Reported found in buchu oil, celery, geranium oil, pennyroyal oil and peppermint oil

Uses

(±)-Isomenthone is a constituent of some commercial essential oils with antimicrobial and antioxidant properties.

Preparation

By hydrogenation of pipertone.

Aroma threshold values

Aroma characteristics at 1.0%: sweet peppermint, minty, fresh, powdery and ethereal with a lift of green spearmint

Taste threshold values

Taste characteristics at 30 ppm: cooling minty peppermint, sweet ethereal herbal spearmint

InChI:InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9-/m1/s1

Synthetic route

Se-phenyl 3,7-dimethyloct-6-eneselenoate (115033-76-6) → 3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) + isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h;	A 12% B n/a C n/a
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Product distribution; mode of addition of TBTH/AIBN or hydroquinone;	A 12% B n/a C n/a
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Yield given. Yields of byproduct given;
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 1.5h; Yield given. Yields of byproduct given;

3,7-dimethyl-6-octenoyl chloride (36392-06-0) → 3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) + isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Product distribution; mode of addition of TBTH/AIBN or Galvinoxyl;	A 10% B n/a C n/a

tetrachloromethane (56-23-5) + 5-hydroxy-3,6-diisopropyl-9-methyl-2,3,5,6,7,8,9,10-octahydro-1H-5,9-methano-benzocycloocten-4-one (15775-51-6) → isomenthone (491-07-6)

Conditions	Yield
unter vermindertem Druck; substance of mp: 110 degree (α-dipiperitone);
unter vermindertem Druck; substance of mp: 94 degree;

thymol (89-83-8) → isomenthone (491-07-6) + Menthone (10458-14-7)

Conditions	Yield
With hydrogen; nickel at 160℃; dl-menthone;

neoisomenthol (3623-53-8) → isomenthone (491-07-6)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid; water

(+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5) → isomenthone (491-07-6)

Conditions	Yield
With sodium In methanol for 2h; Ambient temperature;

pulegone (89-82-7, 3285-04-9, 3391-90-0, 15932-80-6) → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 3h; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen; silica gel; copper In toluene at 140℃; under 7600 Torr; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; under 15001.5 Torr; for 24h; Overall yield = 71 %; chemoselective reaction;	A n/a B n/a

Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) → (Z)-p-menthan-4-ol (3239-03-0) + (Z)-4-isopropyl-1-methylcyclohexan-1-ol (3901-93-7) + cis p-menthanol (3901-95-9) + isomenthone (491-07-6)

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) → (Z)-p-menthan-4-ol (3239-03-0) + (Z)-4-isopropyl-1-methylcyclohexan-1-ol (3901-93-7) + isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) → (Z)-p-menthan-4-ol (3239-03-0) + (Z)-4-isopropyl-1-methylcyclohexan-1-ol (3901-93-7) + isomenthone (491-07-6) + methyl-2 isopropyl-5 cyclohexanone (499-70-7, 3901-91-5, 5206-83-7, 7065-48-7, 13163-73-0, 13163-74-1, 59471-80-6, 116562-19-7, 127911-15-3)

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) → (Z)-p-menthan-4-ol (3239-03-0) + (Z)-4-isopropyl-1-methylcyclohexan-1-ol (3901-93-7) + isomenthone (491-07-6) + methyl-2 isopropyl-5 cyclohexanone (499-70-7, 3901-91-5, 5206-83-7, 7065-48-7, 13163-73-0, 13163-74-1, 59471-80-6, 116562-19-7, 127911-15-3)

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

Se-phenyl 3,7-dimethyloct-6-eneselenoate (115033-76-6) → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Se-methyl citronellselenoate (130350-93-5) → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2.5h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

piperitone (89-81-6, 6091-52-7) + hydrogen + palladium → isomenthone (491-07-6)

piperitone (89-81-6, 6091-52-7) + nickel pumice stone → thymol (89-83-8) + isomenthone (491-07-6)

Conditions	Yield
at 180℃; under 100 Torr; Hydrogenation; dl-piperitone;

piperitone (89-81-6, 6091-52-7) + nickel → thymol (89-83-8) + isomenthone (491-07-6)

Conditions	Yield
at 140℃; under 13680 Torr; im Eisenautoklaven.Hydrogenation; dl-piperitone;

piperitone (89-81-6, 6091-52-7) + palladium → thymol (89-83-8) + isomenthone (491-07-6)

Conditions	Yield
Hydrogenation; dl-piperitone;

(+-)-erythro(?)-2-isopropyl-5-methyl-heptanedioic acid → isomenthone (491-07-6)

Conditions	Yield
With barium dihydroxide at 310 - 330℃;

(+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5) + alcoholic alkaline solution → isomenthone (491-07-6)

neoisomenthol (3623-53-8) + chromic acid mixture → isomenthone (491-07-6)

isomenthol (3623-52-7) + chromic acid mixture → isomenthone (491-07-6)

d-piperitone → isomenthone (491-07-6)

Conditions	Yield
With palladium at 30℃; Hydrogenation;

2-iodo-propane (75-30-9) + 4-methyl-l-formyl-cyclohexanone-(2) → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With sodium ethanolate im geschlossenen Gefaess und Destillieren des Reaktionsprodukts mit Natronlauge;

/PBNZB002--760/ → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With sodium dithionite; sodium hydrogencarbonate; Aliquat R In water; benzene at 80℃; for 2h; Yield given. Yields of byproduct given;

/PBNZB002--770/ → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With sodium dithionite; sodium hydrogencarbonate; Aliquat R In water; benzene at 80℃; for 2.5h; Yield given. Yields of byproduct given;

hydrogenchloride (7647-01-0) + p-menthan-3-one semicarbazone (1686-42-6, 16892-34-5) → isomenthone (491-07-6) + hydrazine carboxamide (4426-72-6, 51433-48-8)

Conditions	Yield
dl-isomenthone-α semicarbazone;

3,7-dimethyl-oct-6-enal (106-23-0, 26489-02-1) → isomenthone (491-07-6) + (+/-)-menthone (491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); 2,3,3,4,4,5-hexamethyl-2-hexanethiol In toluene for 21h; Heating;

isomenthol (3623-52-7) → isomenthone (491-07-6)

Conditions	Yield
With potassium dichromate; sulfuric acid In diethyl ether

chloroform (67-66-3) + isomenthone (491-07-6) → 2-(chloromethylene)-1-isopropyl-4-methylcyclohexane

Conditions	Yield
With titanium tetrachloride; magnesium In tetrahydrofuran at 10 - 25℃; for 1h;	78%

isomenthone (491-07-6) + mercury(II) diacetate (1600-27-7) → (1RS,2SR,4SR)-2-acetoxy-p-menthan-3-one-(2,4-dinitro-phenylhydrazone)

Conditions	Yield
Behandeln des Reaktionsprodukts mit <2,4-Dinitro-phenyl>-hydrazin;

isomenthone (491-07-6) + ammonium formate (540-69-2) → N-((1S)-neomenthyl)-formamide (34048-58-3, 57457-71-3, 83213-88-1, 100049-49-8)

isomenthone (491-07-6) → cis-1-isopropyl-4-methyl-cyclohexane (6069-98-3)

Conditions	Yield
With sulfuric acid Electrolysis;

isomenthone (491-07-6) → (+/-)-2,3-bis-(4-nitro-benzoyloxy)-trans-p-menth-2-ene

Conditions	Yield
With acetic acid; mercury(II) oxide Erwaermen des Reaktionsprodukts mit wss. KOH und anschliessend mit 4-Nitro-benzoylchlorid;

isomenthone (491-07-6) → (+/-)-(3R,6R)-3-isopropyl-6-methyl-1-cyclohexene (1124-26-1, 2230-85-5, 5056-00-8, 5113-93-9, 5256-65-5, 31658-04-5)

Conditions	Yield
(i) TsNHNH2, H2SO4, (ii) MeLi; Multistep reaction;

isomenthone (491-07-6) → (R*,R*)-3,7-dimethyl-6-octanolide (499-54-7, 68330-67-6, 68330-68-7, 130981-75-8, 130981-76-9, 133162-66-0, 133267-37-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane

isomenthone (491-07-6) → (2R*,3R*,6S*)-2-hydroxy-3-methyl-6-isopropylcyclohexanone + (2S*,3R*,6S*)-2-hydroxy-3-methyl-6-isopropylcyclohexanone

Conditions	Yield
Yield given. Multistep reaction;
Multistep reaction;

hydrogenchloride (7647-01-0) + isomenthone (491-07-6) + benzaldehyde (100-52-7) → 2-<α-chloro-benzyl>-p-menthanon-(3) of melting point 119-120 degree

hydrogenchloride (7647-01-0) + isomenthone (491-07-6) + benzaldehyde (100-52-7) → 2-<α-chloro-benzyl>-p-menthanon-(3) of melting point 119-120 degree + 2-<α-chloro-benzyl>-p-menthanon-(3) of melting point 129-130 degree

sulfuric acid (7664-93-9) + isomenthone (491-07-6) → cis-1-isopropyl-4-methyl-cyclohexane (6069-98-3)

Conditions	Yield
Electrolysis;

Upstream product

• 89-82-7 pulegone 
• 72311-09-2 3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen 
• 75-36-5 acetyl chloride 
• 6485-40-1 (R)-Carvone 
• 89-81-6 piperitone 
• 3623-52-7 isomenthol 
• 53282-30-7 trifluoro-methanesulfonic acid 2-methyl-propenyl ester 
• 95465-47-7 potassium menthyl oxide 
• 59781-47-4 r-2-Acetyl-t-3-methyl-c-6-(1-methylethyl)-1-cyclohexanon 
• 74-88-4 methyl iodide 
• 1193-18-6 3-methylcyclohexen-2-one 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 89-78-1 menthol 
• 490-99-3 DL-neomenthol 

Downstream Products

• 1124-26-1 (+/-)-(3R,6R)-3-isopropyl-6-methyl-1-cyclohexene 
• 491-07-6 isomenthone 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 2216-51-5 (-)-menthol 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 3623-53-8 neoisomenthol 
• 907166-70-5 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]pyridine-3-carbohydrazide 
• 13143-66-3 C₁₆H₂₃N₃O 
• 1299427-55-6 C₁₇H₂₃FN₂O 
• 904248-90-4 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-51-2 4-hydroxy-N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-53-4 4-chloro-N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 
• 1299427-52-3 N'-[5-methyl-2-(propan-2-yl)cyclohexylidene]-4-nitrobenzohydrazide 
• 1299427-47-6 4-methyl-N'-[-5-methyl-2-(propan-2-yl)cyclohexylidene]benzohydrazide 

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