Product Name

  • Name

    Carvacrol

  • EINECS 207-889-6
  • CAS No. 499-75-2
  • Article Data180
  • CAS DataBase
  • Density 0.974 g/cm3
  • Solubility Insoluble in water
  • Melting Point 3-4 °C(lit.)
  • Formula C10H14O
  • Boiling Point 237.2 °C at 760 mmHg
  • Molecular Weight 150.221
  • Flash Point 106.7 °C
  • Transport Information UN 3265 8/PG 3
  • Appearance liquid
  • Safety 26-36/37/39-45
  • Risk Codes 22-34
  • Molecular Structure Molecular Structure of 499-75-2 (Carvacrol)
  • Hazard Symbols
  • Synonyms Carvacrol;
  • PSA 20.23000
  • LogP 2.82400

Synthetic route

Conditions
ConditionsYield
With montmorillonite In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 160℃; Temperature; Solvent; Autoclave; Green chemistry; Industrial scale;99%
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux;94%
With toluene-4-sulfonic acid In 1,4-dioxane; chlorobenzene at 180℃; under 2475.2 Torr; for 0.583333h; Irradiation;85%
5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone
7712-46-1

5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With Amberlyst-15 cation exchange resin In toluene at 120 - 150℃; Temperature; Solvent; Reagent/catalyst;98%
(S)-p-mentha-6,8-dien-2-one
2244-16-8, 6485-40-1

(S)-p-mentha-6,8-dien-2-one

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
In water at 180 - 250℃; for 0.166667h;95%
at 160 - 180℃;
carvacryl acetate
6380-28-5

carvacryl acetate

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 18h;94%
(+)-(1S,4S,5R,6R)-1,5,6-trihydroxy-2-menthene

(+)-(1S,4S,5R,6R)-1,5,6-trihydroxy-2-menthene

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With iodine In toluene for 5h; Reflux;94%
Conditions
ConditionsYield
With palladium 10% on activated carbon at 135℃; for 1h; Temperature;91%
5-Isopropenyl-2-methyl-cyclohex-2-enol
99-48-9

5-Isopropenyl-2-methyl-cyclohex-2-enol

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux;90%
carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With tert-butyldimethylsilyl 2-methylpropane-2-sulfonate; platinum(IV) chloride In toluene at 80℃; for 2h; Inert atmosphere; regioselective reaction;87%
With triethylsilyl chloride; triethylamine; sodium iodide In acetonitrile at 4℃;67%
With chloro-trimethyl-silane; water for 3h; Ambient temperature;
In water Heating; Acidic conditions;
With aqueous acid Heating;
(R)-1-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[3.1.0]hexan-3-one
130912-76-4

(R)-1-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[3.1.0]hexan-3-one

A

carvacrol
499-75-2

carvacrol

B

(5S,6S)-5-Bromo-3-isopropyl-6-methyl-cyclohex-2-enone

(5S,6S)-5-Bromo-3-isopropyl-6-methyl-cyclohex-2-enone

Conditions
ConditionsYield
With hydrogen bromide In dichloromethane for 1.5h; Ambient temperature;A 10%
B 85%

A

carvacrol
499-75-2

carvacrol

B

(5R)-5-(1-chloro-1-methylethyl)-2-methylcyclohex-2-enone
85710-71-0

(5R)-5-(1-chloro-1-methylethyl)-2-methylcyclohex-2-enone

Conditions
ConditionsYield
With hydrogenchloride; silica gel In water at 0 - 20℃; for 0.75h; Time;A 11%
B 83%
ortho-cresol
95-48-7

ortho-cresol

isopropyl alcohol
67-63-0

isopropyl alcohol

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With diatomaceous earth phosphoric acid at 135℃; for 6h; Temperature;82.3%
With phosphorus pentoxide
With aluminum (III) chloride In dichloromethane at -5℃; for 4h; Solvent; Reagent/catalyst; Large scale;75.6 kg
2-hydroxy-5-isopropenyl-2-methylcyclohexanone

2-hydroxy-5-isopropenyl-2-methylcyclohexanone

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With phosphorus pentoxide In 1,4-dioxane at 98 - 108℃; for 2h; Solvent;81%
(+)-(4S,5R,6S)-5,6-dihydroxy-1(7),2-menthadiene

(+)-(4S,5R,6S)-5,6-dihydroxy-1(7),2-menthadiene

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h;80%
(+)-Δ5-dehydro-1-hydroxyisocarvomenthol

(+)-Δ5-dehydro-1-hydroxyisocarvomenthol

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With iodine In toluene for 5h; Reflux;80%
p-menth-3-en-2-one
23733-68-8

p-menth-3-en-2-one

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With Cu-C composite catalyst In 5,5-dimethyl-1,3-cyclohexadiene at 190 - 220℃; Solvent; Green chemistry;78%
With copper in charcoal In 5,5-dimethyl-1,3-cyclohexadiene at 190 - 220℃; Concentration; Solvent;77%
With copper in charcoal In 5,5-dimethyl-1,3-cyclohexadiene at 190 - 230℃; Reflux;77%
chloroacetonitrile
107-14-2

chloroacetonitrile

A

carvacrol
499-75-2

carvacrol

B

8-(chloroacetylamino)-p-menth-6-en-2-one
128011-29-0

8-(chloroacetylamino)-p-menth-6-en-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 68%
(+)-Δ5-dehydro-1-hydroxyisocarvomenthol

(+)-Δ5-dehydro-1-hydroxyisocarvomenthol

A

carvacrol
499-75-2

carvacrol

B

carvotanacetone
499-71-8

carvotanacetone

Conditions
ConditionsYield
With iodine In toluene for 3h; Reflux;A 64%
B 26%
formic acid 5-isopropyl-2-methyl-phenyl ester

formic acid 5-isopropyl-2-methyl-phenyl ester

A

carvacrol
499-75-2

carvacrol

B

2-hydroxy-6-isopropyl-3-methyl-benzaldehyde
1665-99-2

2-hydroxy-6-isopropyl-3-methyl-benzaldehyde

Conditions
ConditionsYield
With boron tribromide; iron(III) chloride In chlorobenzene at -15 - 12℃; for 3h; Fries rearrangement;A n/a
B 55%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

A

carvacrol
499-75-2

carvacrol

B

8-(4-chlorobutyramido)-6-p-menthen-2-one

8-(4-chlorobutyramido)-6-p-menthen-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 54%
pentanonitrile
110-59-8

pentanonitrile

A

carvacrol
499-75-2

carvacrol

B

8-valeramido-6-p-menthen-2-one

8-valeramido-6-p-menthen-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 53%
benzonitrile
100-47-0

benzonitrile

A

carvacrol
499-75-2

carvacrol

B

8-benzoylamino-p-menth-6-en-2-one
128011-32-5

8-benzoylamino-p-menth-6-en-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 48%
(R)-1-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[3.1.0]hexan-3-one
130912-76-4

(R)-1-(1-Hydroxy-1-methyl-ethyl)-4-methyl-bicyclo[3.1.0]hexan-3-one

A

carvacrol
499-75-2

carvacrol

B

(5S,6S)-5-Chloro-3-isopropyl-6-methyl-cyclohex-2-enone

(5S,6S)-5-Chloro-3-isopropyl-6-methyl-cyclohex-2-enone

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 1.5h; Ambient temperature;A 40%
B 45%
acetonitrile
75-05-8

acetonitrile

/PRSGG643-3025/

/PRSGG643-3025/

A

carvacrol
499-75-2

carvacrol

B

8-acetylamino-p-menth-6-en-2-one
128011-28-9

8-acetylamino-p-menth-6-en-2-one

C

/PRSGG643-3027/

/PRSGG643-3027/

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃;A n/a
B 44%
C n/a
Isobutyronitrile
78-82-0

Isobutyronitrile

/PRSGG643-3025/

/PRSGG643-3025/

A

carvacrol
499-75-2

carvacrol

B

8-isobutyrylamino-p-menth-6-en-2-one
128011-31-4

8-isobutyrylamino-p-menth-6-en-2-one

C

/PRSGG643-3027/

/PRSGG643-3027/

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃;A n/a
B 42%
C n/a
benzonitrile
100-47-0

benzonitrile

/PRSGG643-3025/

/PRSGG643-3025/

A

carvacrol
499-75-2

carvacrol

B

8-benzoylamino-p-menth-6-en-2-one
128011-32-5

8-benzoylamino-p-menth-6-en-2-one

C

/PRSGG643-3027/

/PRSGG643-3027/

Conditions
ConditionsYield
With sulfuric acid In dibutyl ether at 0 - 20℃;A n/a
B 42%
C n/a
acetonitrile
75-05-8

acetonitrile

A

carvacrol
499-75-2

carvacrol

B

8-acetylamino-p-menth-6-en-2-one
128011-28-9

8-acetylamino-p-menth-6-en-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 38%
propiononitrile
107-12-0

propiononitrile

A

carvacrol
499-75-2

carvacrol

B

8-propioamido-6-p-menthen-2-one

8-propioamido-6-p-menthen-2-one

Conditions
ConditionsYield
With sulfuric acid at -25 - 20℃; Ritter reaction;A n/a
B 34%
chloroacetonitrile
107-14-2

chloroacetonitrile

/PRSGG643-3025/

/PRSGG643-3025/

A

carvacrol
499-75-2

carvacrol

B

8-(chloroacetylamino)-p-menth-6-en-2-one
128011-29-0

8-(chloroacetylamino)-p-menth-6-en-2-one

C

/PRSGG643-3027/

/PRSGG643-3027/

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃;A n/a
B 33%
C n/a
cis-piperitol
65733-27-9

cis-piperitol

carvacrol
499-75-2

carvacrol

Conditions
ConditionsYield
With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 72h;33%
carvacrol
499-75-2

carvacrol

methyl iodide
74-88-4

methyl iodide

carvacrol methyl ether
6379-73-3

carvacrol methyl ether

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide In tetrahydrofuran at 50℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 50℃; Inert atmosphere;
100%
Stage #1: carvacrol With sodium hydroxide In methanol at 20℃; for 0.25h; Williamson Ether Synthesis; Inert atmosphere; Alkaline conditions;
Stage #2: methyl iodide In methanol at 65℃; for 1h; Reagent/catalyst; Williamson Ether Synthesis; Cooling; Inert atmosphere;
84%
With potassium carbonate In acetone at 60℃; for 2h;81%
With methanol
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
carvacrol
499-75-2

carvacrol

2-methyl-5-isopropyl-4-chlorophenol
5665-94-1

2-methyl-5-isopropyl-4-chlorophenol

Conditions
ConditionsYield
With oxygen; lithium chloride; copper dichloride In acetic acid at 80℃; for 6h; regioselective reaction;99%
With sulfuryl dichloride In dichloromethane at 0 - 20℃;82%
With sulfuryl dichloride In tetrachloromethane at 0 - 20℃; for 0.75h;81%
carvacrol
499-75-2

carvacrol

allyl bromide
106-95-6

allyl bromide

2-(allyloxy)-4-isopropyl-1-methylbenzene
29652-98-0

2-(allyloxy)-4-isopropyl-1-methylbenzene

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydrogencarbonate In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: allyl bromide In dimethyl sulfoxide at 20℃; for 8h;
98%
With water; sodium hydroxide In acetone Williamson Ether Synthesis; Reflux;76%
Stage #1: carvacrol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: allyl bromide In N,N-dimethyl-formamide Inert atmosphere;
70%
With potassium carbonate; acetone
carvacrol
499-75-2

carvacrol

2-(bromomethyl)naphthalene
3163-27-7

2-(bromomethyl)naphthalene

1-((5-isopropyl-2-methylphenoxy)methyl)naphthalene

1-((5-isopropyl-2-methylphenoxy)methyl)naphthalene

Conditions
ConditionsYield
Stage #1: carvacrol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2-(bromomethyl)naphthalene In N,N-dimethyl-formamide Inert atmosphere;
98%
carvacrol
499-75-2

carvacrol

2-(4-chlorophenyl) malononitrile
32122-64-8

2-(4-chlorophenyl) malononitrile

2-(4-chlorophenyl)-2-(4-hydroxy-2-isopropyl-5-methylphenyl)malononitrile

2-(4-chlorophenyl)-2-(4-hydroxy-2-isopropyl-5-methylphenyl)malononitrile

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 60℃; for 18h; Inert atmosphere; Sealed tube;98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

carvacrol
499-75-2

carvacrol

5-isopropyl-2-methylphenoxytrimethylsilane
66760-13-2

5-isopropyl-2-methylphenoxytrimethylsilane

Conditions
ConditionsYield
With triethylamine In benzene97%
Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

carvacrol
499-75-2

carvacrol

C31H42O3Si
66760-15-4

C31H42O3Si

Conditions
ConditionsYield
With triethylamine In benzene97%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

carvacrol
499-75-2

carvacrol

5-isopropyl-2-methylphenyl trifluoromethanesulfonate
63028-16-0

5-isopropyl-2-methylphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 23℃; for 3h;97%
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
carvacrol
499-75-2

carvacrol

4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

2-methyl-5-isopropylphenyl 4-fluorobenzenesulfonate

2-methyl-5-isopropylphenyl 4-fluorobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;97%
carvacrol
499-75-2

carvacrol

3-nitrobenzenesulphonyl chloride
121-51-7

3-nitrobenzenesulphonyl chloride

2-methyl-5-isopropylphenyl 3-nitrobenzenesulfonate

2-methyl-5-isopropylphenyl 3-nitrobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;97%
carvacrol
499-75-2

carvacrol

benzoyl chloride
98-88-4

benzoyl chloride

5-isopropyl-2-methylphenyl benzoate
100752-52-1

5-isopropyl-2-methylphenyl benzoate

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide; Amberlyst A26
Stage #2: benzoyl chloride In acetone at 20℃; for 0.25h; Further stages.;
96%
With aluminum oxide; sodium hydroxide microwave irradiation;90%
With triethylamine In dichloromethane at 0 - 20℃; for 11h; Inert atmosphere;82%
im Druckrohr;
With picoline In dichloromethane for 1h; Reflux;
carvacrol
499-75-2

carvacrol

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

2-methyl-5-isopropylphenyl 2-nitrobenzenesulfonate

2-methyl-5-isopropylphenyl 2-nitrobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;96%
carvacrol
499-75-2

carvacrol

2-methyl-5-isopropyl-4-bromophenol
121665-99-4

2-methyl-5-isopropyl-4-bromophenol

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In chloroform for 0.0333333h;95%
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 0.166667h;93%
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 23℃; for 0.166667h;93%
carvacrol
499-75-2

carvacrol

α-halo acetic acid

α-halo acetic acid

2-(5-isopropyl-2-methylphenoxy)acetic acid
19728-20-2

2-(5-isopropyl-2-methylphenoxy)acetic acid

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide
Stage #2: α-halo acetic acid In acetone for 0.333333h; Further stages.;
95%
carvacrol
499-75-2

carvacrol

3,3-dimethyl-allyl chloride
503-60-6

3,3-dimethyl-allyl chloride

4-isopropyl-1-methyl-2-((3-methylbut-2-en-1-yl)oxy)benzene

4-isopropyl-1-methyl-2-((3-methylbut-2-en-1-yl)oxy)benzene

Conditions
ConditionsYield
Stage #1: carvacrol With potassium carbonate In acetone at 20℃; for 0.166667h;
Stage #2: 3,3-dimethyl-allyl chloride In acetone at 80℃; for 4h;
95%
carvacrol
499-75-2

carvacrol

4-bromobenzenesulfonyl chloride
98-58-8

4-bromobenzenesulfonyl chloride

2-methyl-5-isopropylphenyl 4-bromobenzenesulfonate

2-methyl-5-isopropylphenyl 4-bromobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;95%
carvacrol
499-75-2

carvacrol

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-isopropyl-1-methyl-2-((4-nitrobenzyl)oxy)benzene

4-isopropyl-1-methyl-2-((4-nitrobenzyl)oxy)benzene

Conditions
ConditionsYield
Stage #1: carvacrol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide Inert atmosphere;
95%
carvacrol
499-75-2

carvacrol

propionyl chloride
79-03-8

propionyl chloride

3-(isopropyl)-6-methylphenyl propionate
157252-17-0

3-(isopropyl)-6-methylphenyl propionate

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide; Amberlyst A26
Stage #2: propionyl chloride In acetone at 20℃; for 0.166667h; Further stages.;
94%
With aluminum oxide; sodium hydroxide microwave irradiation;91%
With triethylamine In dichloromethane at 0 - 20℃; for 11h; Inert atmosphere;75%
carvacrol
499-75-2

carvacrol

acetyl chloride
75-36-5

acetyl chloride

carvacryl acetate
6380-28-5

carvacryl acetate

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide; Amberlyst A26
Stage #2: acetyl chloride In acetone at 20℃; for 0.166667h; Further stages.;
94%
With aluminum oxide; sodium hydroxide microwave irradiation;94%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3.26667h;86%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

carvacrol
499-75-2

carvacrol

2-(5'-isopropyl-2'-methyl-phenoxymethyl)-benzoic acid

2-(5'-isopropyl-2'-methyl-phenoxymethyl)-benzoic acid

Conditions
ConditionsYield
Stage #1: carvacrol With sodium methylate In methanol salt formation;
Stage #2: 2-benzofuran-1(3H)-one at 150 - 160℃; for 4h; Addition; ring cleavage;
94%
carvacrol
499-75-2

carvacrol

ethyl halide

ethyl halide

2-ethoxy-4-isopropyl-1-methylbenzene
4732-13-2

2-ethoxy-4-isopropyl-1-methylbenzene

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide; Amberlite IRA 400
Stage #2: ethyl halide In acetone for 0.583333h; Further stages.;
94%
carvacrol
499-75-2

carvacrol

n-butyl halide

n-butyl halide

2-butoxy-4-isopropyl-1-methylbenzene

2-butoxy-4-isopropyl-1-methylbenzene

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide
Stage #2: n-butyl halide In acetone for 0.583333h; Further stages.;
94%
carvacrol
499-75-2

carvacrol

n-propyl halide

n-propyl halide

4-isopropyl-1-methyl-2-propoxybenzene
5648-33-9

4-isopropyl-1-methyl-2-propoxybenzene

Conditions
ConditionsYield
Stage #1: carvacrol With sodium hydroxide
Stage #2: n-propyl halide In acetone for 0.5h; Further stages.;
94%
carvacrol
499-75-2

carvacrol

CH3CH2-Hal

CH3CH2-Hal

2-ethoxy-4-isopropyl-1-methylbenzene
4732-13-2

2-ethoxy-4-isopropyl-1-methylbenzene

Conditions
ConditionsYield
With aluminum oxide; sodium hydroxide microwave irradiation;94%
carvacrol
499-75-2

carvacrol

(Z)-4-(2-bromovinyl)benzoic acid
959576-29-5

(Z)-4-(2-bromovinyl)benzoic acid

(Z)-5-isopropyl-2-methylphenyl-4-(2-bromovinyl)benzoate
1202386-11-5

(Z)-5-isopropyl-2-methylphenyl-4-(2-bromovinyl)benzoate

Conditions
ConditionsYield
Stage #1: carvacrol; (Z)-4-(2-bromovinyl)benzoic acid With dmap In N,N-dimethyl-formamide; benzene for 0.166667h;
Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide; benzene at 20℃; for 24h; optical yield given as %de; stereoselective reaction;
94%
carvacrol
499-75-2

carvacrol

2-chloro-N-(3,4-dichlorophenyl)acetamide
20149-84-2

2-chloro-N-(3,4-dichlorophenyl)acetamide

C18H19Cl2NO2
1228237-34-0

C18H19Cl2NO2

Conditions
ConditionsYield
With sodium hydroxide In acetone for 0.0416667h; Microwave irradiation;94%

5-Isopropyl-2-methylphenol Chemical Properties

Molecular structure of Carvacrol (CAS NO.499-75-2):


IUPAC Name: 2-Methyl-5-propan-2-ylphenol 
Molecular Weight: 150.21756 g/mol
Molecular Formula: C10H14
Density: 0.974 g/cm3 
Melting Point: 3-4 °C(lit.)
Boiling Point: 237.2 °C at 760 mmHg 
Flash Point: 106.7 °C
Index of Refraction: 1.523
Molar Refractivity: 47.14 cm3
Molar Volume: 154.2 cm3
Polarizability: 18.68×10-24 cm3
Surface Tension: 34.9 dyne/cm 
Enthalpy of Vaporization: 49.32 kJ/mol
Vapour Pressure: 0.0296 mmHg at 25 °C 
Water Solubility: insoluble
XLogP3: 3.1
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Tautomer Count: 9
Exact Mass: 150.104465
MonoIsotopic Mass: 150.104465
Topological Polar Surface Area: 20.2
Heavy Atom Count: 11
Complexity: 120
Canonical SMILES: CC1=C(C=C(C=C1)C(C)C)O
InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
InChIKey: RECUKUPTGUEGMW-UHFFFAOYSA-N
EINECS: 207-889-6
Product Categories: Alcohols and Derivatives; Miscellaneous Natural Products

5-Isopropyl-2-methylphenol Uses

 Carvacrol (CAS NO.499-75-2) is used for the preparation of spices, fungicides and disinfectants. It also is used as the spices in toothpaste, soap and other daily necessities. Carvacrol also can be used as food flavor.

5-Isopropyl-2-methylphenol Production

 Carvacrol may be synthetically prepared by the action of nitrous acid on 1-methyl-2-amino-4-propyl benzene; by the fusion of cymol sulfonic acid with caustic potash; by prolonged heating of five parts of camphor with one part of iodine; or by heating carvol with glacial phosphoric acid or by performing a dehydrogenation of carvone with a Pd/C catalyst.

5-Isopropyl-2-methylphenol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 100mg/kg (100mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 46, 1959.
dog LDLo intravenous 310mg/kg (310mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Therapie. Vol. 3, Pg. 109, 1948.
frog LDLo subcutaneous 75mg/kg (75mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 46, 1959.
mouse LD50 intraperitoneal 73300ug/kg (73.3mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Quarterly Journal of Crude Drug Research. Vol. 19, Pg. 1, 1981.
mouse LD50 intravenous 80mg/kg (80mg/kg) BEHAVIORAL: SLEEP Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.
mouse LD50 subcutaneous 680mg/kg (680mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.
rabbit LDLo oral 100mg/kg (100mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 161, Pg. 196, 1931.
rabbit LDLo skin 2700mg/kg (2700mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 38, Pg. 366, 1949.
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 46, 1959.
rat LD50 oral 810mg/kg (810mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

5-Isopropyl-2-methylphenol Safety Profile

Hazard Codes: CorrosiveC
Risk Statements: 22-34 
R22:Harmful if swallowed. 
R34:Causes burns.
Safety Statements: 26-36/37/39-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 3
WGK Germany: 3
RTECS: FI1225000
HazardClass: 8
PackingGroup: III
Hazardous Substances Data: 499-75-2(Hazardous Substances Data)

5-Isopropyl-2-methylphenol Specification

 Carvacrol (CAS NO.499-75-2) is also named as 1-Hydroxy-2-methyl-5-isopropylbenzene ; 1-Methyl-2-hydroxy-4-isopropylbenzene ; 2-Hydroxy-p-cymene ; 2-Methyl-5-(1-methylethyl)phenol ; 2-Methyl-5-isopropylphenol ; 2-p-Cymenol ; 3-Isopropyl-6-methylphenol ; 4-06-00-03331 (Beilstein Handbook Reference) ; 5-Isopropyl-2-methylphenol ; 5-Isopropyl-o-cresol ; 6-Methyl-3-isopropylphenol ; AI3-03438 ; Antioxine ; BRN 1860514 ; CCRIS 7450 ; Caswell No. 511 ; Cymene-2-ol, p- ; EPA Pesticide Chemical Code 022104 ; FEMA No. 2245 ; HSDB 906 ; Isopropyl-o-cresol ; Karvakrol ; NSC 6188 ; Phenol, 2-methyl-5-(1-methylethyl)- ; Phenol, 3-isopropyl-6-methyl- ; Phenol, 5-isopropyl-2-methyl- ; UNII-9B1J4V995Q ; o-Cresol, 5-isopropyl- ; o-Thymol ; p-Cymen-2-ol ; p-Cymene, 2-hydroxy- . Carvacrol (CAS NO.499-75-2) is colorless to pale yellow viscous oil with a bit thick. It is stable and combustible. It can be incompatible with strong bases, strong oxidizing agents. It is soluble in ethanol, ethyl ether, propylene glycol and alkali, insoluble in water. It also can miscible in oil.

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