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89-83-8

Basic Information
CAS No.: 89-83-8
Name: Thymol
Article Data: 217
Molecular Structure:
Molecular Structure of 89-83-8 (Thymol)
Formula: C10H14O
Molecular Weight: 150.221
Synonyms: Thymol(8CI);1-Methyl-3-hydroxy-4-isopropylbenzene;2-Hydroxy-1-isopropyl-4-methylbenzene;2-Isopropyl-5-methylphenol;3-Hydroxy-p-cymene;3-Methyl-6-isopropylphenol;5-Methyl-2-(1-methylethyl)phenol;5-Methyl-2-isopropyl-1-phenol;5-Methyl-2-isopropylphenol;6-Isopropyl-3-methylphenol;6-Isopropyl-m-cresol;Apiguard;NSC 11215;NSC47821;NSC 49142;Thyme camphor;Thymol Chrystals;m-Thymol;p-Cymen-3-ol;Thymol;
EINECS: 201-944-8
Density: 0.974 g/cm3
Melting Point: 48-51 °C(lit.)
Boiling Point: 233 °C at 760 mmHg
Flash Point: 102.2 °C
Solubility: 0.1 g/100 mL (20 °C) in water
Appearance: white crystals or powder with a pungent odour
Hazard Symbols: CorrosiveC, DangerousN
Risk Codes: 22-34-51/53
Safety: 26-28-36/37/39-45-61-28A
Transport Information: UN 3261 8/PG 3
PSA: 20.23000
LogP: 2.82400
Synthetic route
5333-40-4

2-isopropyl-5-methylphenoxyacetic acid

89-83-8

thymol

Conditions
ConditionsYield
Stage #1: 2-isopropyl-5-methylphenoxyacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating;
Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.;
99%
18612-99-2

2-isopropenyl-5-methylphenol

89-83-8

thymol

Conditions
ConditionsYield
With hydrogen; nickel In ethanol at 30℃; under 2280 - 3800 Torr; Catalytic hydrogenation;98%
With nickel at 140 - 160℃; Hydrogenation;
With palladium 10% on activated carbon; ammonium formate In ethanol; n-heptane at 20℃; for 6h; Reflux;98 kg
1076-56-8

Thymol methyl ether

89-83-8

thymol

Conditions
ConditionsYield
With aluminium trichloride In ethanethiol at 0℃; for 0.5h;95.5%
With aluminium trichloride In ethanethiol at 0℃; for 0.5h;95.5%
14002-90-5

4,7-dimethyl-coumarin

A

18612-99-2

2-isopropenyl-5-methylphenol

B

89-83-8

thymol

Conditions
ConditionsYield
With potassium hydroxide In ethylene glycol for 1h; Mechanism; Reflux;A 90%
B 8%
89-68-9

4-chloro-2-isopropyl-5-methylphenol

89-83-8

thymol

Conditions
ConditionsYield
With 1.5mol% Pd/C; hydrogen; sodium hydrogencarbonate In methanol at 20℃; for 1h; regioselective reaction;80%
With alkaline solution; iron at 170 - 200℃;
With potassium hydroxide; sodium hydroxide; nickel-copper catalyst at 180℃; under 22800 Torr; Hydrogenation;
With potassium hydroxide; sodium hydroxide; nickel-manganese catalyst at 180℃; under 22800 Torr; Hydrogenation;
528-79-0

2-isopropyl-5-methylphenyl acetate

89-83-8

thymol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 22h;79%
108-39-4

3-methyl-phenol

89-83-8

thymol

Conditions
ConditionsYield
With G-type solid acid catalyst at 180 - 200℃; under 1500.15 Torr; Temperature;76.3%
at 150 - 350℃;
With boric acid; oxalic acid at 140℃;
Conditions
ConditionsYield
With N-Bromosuccinimide; N,N-dimethyl-formamide75%
75-29-6

isopropyl chloride

108-39-4

3-methyl-phenol

89-83-8

thymol

Conditions
ConditionsYield
With sulfuric acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 120 - 130℃; for 2h; Reagent/catalyst;56.8%
With aluminium trichloride; 1,2-dichloro-ethane at -10℃;
With aluminium trichloride
256637-50-0

2-isopropyl-5-methylphenyl trifluoromethanesulfonate

A

99-87-6

4-methylisopropylbenzene

B

89-83-8

thymol

Conditions
ConditionsYield
With lithium; nickel dichloride In tetrahydrofuran at 20℃; Reduction;A 44%
B 52%
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    Product Name: Thymol CAS: 89-83-8 MF: C10H14O MW: 150.22 EINECS: 201-944-8 Mol File: 89-83-8.mol Thymol Structure Thymol Chemical Properties Melting point 48-51 °C(lit.) Boiling point 232 °C(lit.) density 0.965

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

1. Introduction of Thymol

Thymol (CAS No.89-83-8), it also can be called 2-Isopropyl-5-methyl phenol ; 5-Methyl-2-(1-methylethyl)phenol ; 1-Hydroxy-5-methyl-2-isopropylbenzene ; 1-Methyl-3-hydroxy-4-isopropylbenzene ; 2-Hydroxy-1-isopropyl-4-methylbenzene ; 3-Hydroxy-1-methyl-4-isopropylbenzene ; 3-Hydroxy-p-cymene ; 3-Methyl-6-isopropylphenol ; 3-p-cymenol . It is white crystals or powder with a pungent odour. It is the active antiseptic ingredient in the toothpaste Euthymol.

2. Properties of Thymol

(1) H bond acceptors: 1 (2) H bond donors: 1 (3) Freely Rotating Bonds: 2
(4) Polar Surface Area: 20.23 Å2 (5) Index of Refraction: 1.523  (6) Molar Refractivity: 47.14 cm3
(7) Molar Volume: 154.2 cm3 (8) Surface Tension: 34.9 dyne/cm  (9) Density: 0.974 g/cm3
(10) Flash Point: 101 °C (11) Melting Point: 48-52 ºC  (12) Enthalpy of Vaporization: 48.88 kJ/mol
(13) Boiling Point: 233 °C at 760 mmHg  (14) Vapour Pressure: 0.0376 mmHg at 25°C

3. Structure descriptors of Thymol

IUPAC Name: 5-methyl-2-propan-2-ylphenol

InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3

InChIKey: MGSRCZKZVOBKFT-UHFFFAOYSA-N

Canonical SMILES : CC1=CC(=C(C=C1)C(C)C)O 

4. Uses of Thymol

1. It has been used to successfully control varroa mites and prevent fermentation and the growth of mould in bee colonies.
2. It laso has a minor use in bookbinding: before rebinding, books with mold damage can be sealed in bags with thymol crystals to kill fungal spores.
3. Thymol has been used in alcohol solutions and in dusting powders for the treatment of tinea (ringworm) infections.
4. Thymol was used to treat hookworm infections in the US.
5. It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash.

5.Safety information of Thymol

Hazard Codes: Corrosive,Dangerous
Risk Statements: 22-34-51/53
R22:Harmful if swallowed.
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-28-36/37/39-45-61-28
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
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.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3261 8/PG 3
WGK Germany: 2
RTECS: XP2275000
HazardClass: 8
PackingGroup: III
HS Code: 29071900
Hazardous Substances Data: 89-83-8(Hazardous Substances Data)

6. Toxicity data of Thymol

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 250mg/kg (250mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.
dog LDLo intravenous 150mg/kg (150mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Therapie. Vol. 3, Pg. 109, 1948.
frog LDLo subcutaneous 150mg/kg (150mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.
guinea pig LD50 oral 880mg/kg (880mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: GASTRITIS

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
guinea pig LDLo intraperitoneal 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.
guinea pig LDLo subcutaneous 1100mg/kg (1100mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.
mouse LD50 intraperitoneal 110mg/kg (110mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Quarterly Journal of Crude Drug Research. Vol. 19, Pg. 1, 1981.
mouse LD50 intravenous 100mg/kg (100mg/kg) BEHAVIORAL: SLEEP Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.
mouse LD50 oral 640mg/kg (640mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. Vol. 5, Pg. 111, 1956.
mouse LD50 subcutaneous 243mg/kg (243mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. Vol. 5, Pg. 111, 1956.
rabbit LDLo intravenous 60mg/kg (60mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.
rabbit LDLo oral 750mg/kg (750mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 17, Pg. 261, 1921.
rat LD50 oral 980mg/kg (980mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LDLo subcutaneous 1600mg/kg (1600mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 172, 1959.