Carvone
carvacrol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With Amberlyst-15 cation exchange resin In toluene at 120 - 150℃; Temperature; Solvent; Reagent/catalyst; | 98% |
(S)-p-mentha-6,8-dien-2-one
carvacrol
Conditions | Yield |
---|---|
In water at 180 - 250℃; for 0.166667h; | 95% |
at 160 - 180℃; |
Conditions | Yield |
---|---|
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 18h; | 94% |
carvacrol
Conditions | Yield |
---|---|
With iodine In toluene for 5h; Reflux; | 94% |
carvacrol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon at 135℃; for 1h; Temperature; | 91% |
Conditions | Yield |
---|---|
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux; | 90% |
(R)-Carvone
carvacrol
Conditions | Yield |
---|---|
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
A
carvacrol
Conditions | Yield |
---|---|
With hydrogen bromide In dichloromethane for 1.5h; Ambient temperature; | A 10% B 85% |
(R)-Carvone
A
carvacrol
B
(5R)-5-(1-chloro-1-methylethyl)-2-methylcyclohex-2-enone
Conditions | Yield |
---|---|
With hydrogenchloride; silica gel In water at 0 - 20℃; for 0.75h; Time; | A 11% B 83% |
Conditions | Yield |
---|---|
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 |
carvacrol
Conditions | Yield |
---|---|
With phosphorus pentoxide In 1,4-dioxane at 98 - 108℃; for 2h; Solvent; | 81% |
carvacrol
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; | 80% |
carvacrol
Conditions | Yield |
---|---|
With iodine In toluene for 5h; Reflux; | 80% |
p-menth-3-en-2-one
carvacrol
Conditions | Yield |
---|---|
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% |
(R)-Carvone
chloroacetonitrile
A
carvacrol
B
8-(chloroacetylamino)-p-menth-6-en-2-one
Conditions | Yield |
---|---|
With sulfuric acid at -25 - 20℃; Ritter reaction; | A n/a B 68% |
Conditions | Yield |
---|---|
With iodine In toluene for 3h; Reflux; | A 64% B 26% |
Conditions | Yield |
---|---|
With boron tribromide; iron(III) chloride In chlorobenzene at -15 - 12℃; for 3h; Fries rearrangement; | A n/a B 55% |
Conditions | Yield |
---|---|
With sulfuric acid at -25 - 20℃; Ritter reaction; | A n/a B 54% |
Conditions | Yield |
---|---|
With sulfuric acid at -25 - 20℃; Ritter reaction; | A n/a B 53% |
(R)-Carvone
benzonitrile
A
carvacrol
B
8-benzoylamino-p-menth-6-en-2-one
Conditions | Yield |
---|---|
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
A
carvacrol
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 1.5h; Ambient temperature; | A 40% B 45% |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 20℃; | A n/a B 44% C n/a |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 20℃; | A n/a B 42% C n/a |
Conditions | Yield |
---|---|
With sulfuric acid In dibutyl ether at 0 - 20℃; | A n/a B 42% C n/a |
(R)-Carvone
acetonitrile
A
carvacrol
B
8-acetylamino-p-menth-6-en-2-one
Conditions | Yield |
---|---|
With sulfuric acid at -25 - 20℃; Ritter reaction; | A n/a B 38% |
Conditions | Yield |
---|---|
With sulfuric acid at -25 - 20℃; Ritter reaction; | A n/a B 34% |
chloroacetonitrile
A
carvacrol
B
8-(chloroacetylamino)-p-menth-6-en-2-one
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 20℃; | A n/a B 33% C n/a |
cis-piperitol
carvacrol
Conditions | Yield |
---|---|
With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 72h; | 33% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
2-(4-chlorophenyl) malononitrile
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 60℃; for 18h; Inert atmosphere; Sealed tube; | 98% |
chloro-trimethyl-silane
carvacrol
5-isopropyl-2-methylphenoxytrimethylsilane
Conditions | Yield |
---|---|
With triethylamine In benzene | 97% |
Conditions | Yield |
---|---|
With triethylamine In benzene | 97% |
trifluoromethylsulfonic anhydride
carvacrol
5-isopropyl-2-methylphenyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 23℃; for 3h; | 97% |
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 97% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 96% |
carvacrol
2-methyl-5-isopropyl-4-bromophenol
Conditions | Yield |
---|---|
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
2-(5-isopropyl-2-methylphenoxy)acetic acid
Conditions | Yield |
---|---|
Stage #1: carvacrol With sodium hydroxide Stage #2: α-halo acetic acid In acetone for 0.333333h; Further stages.; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: carvacrol With sodium hydroxide; Amberlite IRA 400 Stage #2: ethyl halide In acetone for 0.583333h; Further stages.; | 94% |
Conditions | Yield |
---|---|
Stage #1: carvacrol With sodium hydroxide Stage #2: n-butyl halide In acetone for 0.583333h; Further stages.; | 94% |
Conditions | Yield |
---|---|
Stage #1: carvacrol With sodium hydroxide Stage #2: n-propyl halide In acetone for 0.5h; Further stages.; | 94% |
Conditions | Yield |
---|---|
With aluminum oxide; sodium hydroxide microwave irradiation; | 94% |
carvacrol
(Z)-4-(2-bromovinyl)benzoic acid
(Z)-5-isopropyl-2-methylphenyl-4-(2-bromovinyl)benzoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In acetone for 0.0416667h; Microwave irradiation; | 94% |
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: C10H14O
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
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.
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.
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. |
Hazard Codes: C
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)
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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