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Cas Database

Name	Isomenthone	EINECS	207-727-4
CAS No.	491-07-6	Density	0.881g/cm³
PSA	17.07000	LogP	2.64770
Solubility	N/A	Melting Point	-35 °C
Formula	C10H18 O	Boiling Point	205°Cat760mmHg
Molecular Weight	372.244	Flash Point	72.8°C
Transport Information	N/A	Appearance	N/A
Safety	A skin irritant. When heated to decomposition it emits acrid smoke and fumes.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Cyclohexanone,5-methyl-2-(1-methylethyl)-, cis-; p-Menthan-3-one, cis- (8CI); (?à)-Isomenthone; Isomenthone;cis-Menthone; cis-p-Menthan-3-one; cis-p-Menthone; dl-Isomenthone; a-Isomenthone	Article Data	74

Isomenthone Synthetic route

: 115033-76-6
Se-phenyl 3,7-dimethyloct-6-eneselenoate

A: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

: 491-07-6
isomenthone

: 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
(+/-)-menthone

Conditions

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;

: 36392-06-0
3,7-dimethyl-6-octenoyl chloride

A: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

: 491-07-6
isomenthone

: 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
(+/-)-menthone

Conditions

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

: 56-23-5
tetrachloromethane

: 15775-51-6
5-hydroxy-3,6-diisopropyl-9-methyl-2,3,5,6,7,8,9,10-octahydro-1H-5,9-methano-benzocycloocten-4-one

: 491-07-6
isomenthone

Conditions

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

: 89-83-8
thymol

: 491-07-6
isomenthone

B: 10458-14-7
Menthone

Conditions

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

: 3623-53-8
neoisomenthol

: 491-07-6
isomenthone

Conditions

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

: 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
(+/-)-menthone

: 491-07-6
isomenthone

Conditions

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

: 89-82-7, 3285-04-9, 3391-90-0, 15932-80-6
pulegone

: 491-07-6
isomenthone

: 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
(+/-)-menthone

Conditions

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

: 99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5
Menthane

A: 3239-03-0
(Z)-p-menthan-4-ol

B: 3901-93-7
(Z)-4-isopropyl-1-methylcyclohexan-1-ol

C: 3901-95-9
cis p-menthanol

: 491-07-6
isomenthone

Conditions

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

: 99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5
Menthane

A: 3239-03-0
(Z)-p-menthan-4-ol

B: 3901-93-7
(Z)-4-isopropyl-1-methylcyclohexan-1-ol

: 491-07-6
isomenthone

: 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
(+/-)-menthone

Conditions

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

: 99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5
Menthane

A: 3239-03-0
(Z)-p-menthan-4-ol

B: 3901-93-7
(Z)-4-isopropyl-1-methylcyclohexan-1-ol

: 491-07-6
isomenthone

: 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
methyl-2 isopropyl-5 cyclohexanone

Conditions

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

Isomenthone Chemical Properties

IUPAC Name: (2R,5R)-2-Isopropyl-5-methyl-cyclohexan-1-one
CAS: 491-07-6
EINECS: 207-727-4
Following is the Molecular Structure of Isomenthone (491-07-6):

SMILES: O=C1C[C@H](C)CC[C@@H]1C(C)C
InChI: InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9-/m1/s1
InChIKey: NFLGAXVYCFJBMK-RKDXNWHRBG
Std.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
Std.InChIKey: NFLGAXVYCFJBMK-RKDXNWHRSA-N
Molecular Formula: C₁₀H₁₈O
Molecular Weight: 154.25
Boiling Point: 205℃ at 760 mmHg
Flash Point: 72.8℃
Molar Volume: 175cm³
Density: 0.881g/cm³
Index of Refraction: 1.442
Molar Refractivity: 46.37cm³
Surface Tension: 27.2dyne/cm
Polarizability: 18.38 10^-24cm³
Enthalpy of Vaporization: 44.12kJ/mol
Vapour Pressure: 0.256mmHg at 25℃

Isomenthone Uses

Isomenthone (491-07-6) can be used as a food spice by GB 2760--1996.

Isomenthone Toxicity Data With Reference

skn-rbt 500 mg/24H MLD

FCTXAV Food and Cosmetics Toxicology. 14 (1976),315.

Isomenthone Consensus Reports

Reported in EPA TSCA Inventory.

Isomenthone Safety Profile

This chemical is a skin irritant.

Isomenthone Specification

Isomenthone (491-07-6),which also can be called for (±)-cis-p-Menthan-3-one ; (z)-Cyclohexanon ; (z)-p-Menthan-3-on ; 5-Methyl-2-(1-methylethyl)-,cis-Cyclohexanone ; 5-Methyl-2-(1-methylethyl)cyclohexanone ; cis-Cyclohexanon ; cis-Menthone ; cis-p-Menthan-3-one . Isomenthone (491-07-6) is a colorless slightly like oily liquid and it's insoluble in water, soluble in Ethanol and oil.When heated to decomposition it emits acrid smoke and fumes.

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