3D Mol Similar

Thymol

: Iupac Name：5-methyl-2-propan-2-ylphenol; CAS No.: 89-83-8; Molecular Weight：150.21756; Modify Date.: 2023-02-24 12:29; Introduction: Thymol is an antimicrobial compound which can increase the efficacy of antibiotics involving drug resistant bacteria. It inhibits growth and lactate production as well as reduces cellular glucose uptake within the bacteria. View more+

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1. Names and Identifiers

: 1.1 Name; Thymol; 1.2 Synonyms; 1-hydroxy-2-isopropyl-5-methylbenzene 1-methyl-4-isopropyl-3-hydroxybenzene 2-Hydroxy-1-isopropyl-4-methylbenzene 2-isopropyl-5-methyl-pheno 2-isopropyl-5-methylphenol 2-Isopropyl-5-methyl-phenol 2-Isopropyl-5-methylphenol (thymol) 2-Isopropyl-5-methylphenyl sulfate 3-Hydroxy-1-methyl-4-isopropylbenzene 3-hydroxy-4-isopropyl-1-methylbenzene 3-hydroxy-p-cymen 3-methyl-6-(2-propyl)-phenol 3-Methyl-6-isopropylphenol 3-methyl-6-isopropyl-phenol 3-p-Cymenol 5-methyl-2-(1-methylethyl)phenol 5-methyl-2-(propan-2-yl)phenol 5-methyl-2-(propan-2-yl)phenyl sulfate 5-Methyl-2-isopropylphenol 5-methyl-2-propan-2-ylphenol 6-Isopropyl-3-methylphenol 6-Isopropyl-m-cresol EINECS 201-944-8 Isopropyl cresol MFCD00005869 Phenol, 5-methyl-2-(1-methylethyl)- Phenol, 5-methyl-2-(1-methylethyl)-, hydrogen sulfate, ion(1-) Thyme camphor Thymic acid thymol sulfate thymol sulfate(1-); View all

1.3 CAS No.: 89-83-8

1.4 CID: 6989

1.5 EINECS(EC#): 201-944-8

1.6 Molecular Formula: C10H14O (isomer)

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

1.8 InChIkey: MGSRCZKZVOBKFT-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=CC(=C(C=C1)C(C)C)O

1.10 Isomers Smiles: CC1=CC(=C(C=C1)C(C)C)O

2. Properties

2.1 Density: 0.965

2.1 Melting point: 48-52℃

2.1 Boiling point: 232℃

2.1 Refractive index: 1.5227 (20 C)

2.1 Flash Point: 102℃

2.1 Precise Quality: 150.10400

2.1 PSA: 20.23000

2.1 logP: 2.82400

2.1 Solubility: ethanol: soluble50mg/mL

2.2 Appearance: white crystals or powder with a pungent odour

2.3 Storage: Thymol should be stored in well-closed, light-resistant containers,in a cool, dry, place. Thymol is affected by light.

2.4 Chemical Properties: white crystals or powder with a pungent odour

2.5 Color/Form: COLORLESS CRYSTALS, OFTEN LARGE, OR WHITE CRYSTALLINE POWDER
PLATES FROM ACETIC ACID OR ACETONE

2.6 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.7 Odor: Odor of thyme

2.8 Odor Threshold: 86 to 790 ppb

2.9 PH: Solution in alcohol is neutral to litmus

2.10 pKa: 10.59±0.10(Predicted)

2.11 Water Solubility: 0.1 g/100 mL (20 oC)

2.12 Spectral Properties: INDICES OF REFRACTION: 1.5227 @ 20 DEG C/D; 1.5204 @ 25 DEG C/D
MAX ABSORPTION (CYCLOHEXANE): 276 NM (LOG E= 3.34), 282 NM (LOG E= 3.34)
Intense mass spectral peaks: 135 m/z (100%), 150 m/z (38%), 91 m/z (15%), 136 m/z (10%)
IR: 6256 (Coblentz Society Spectral Collection)
UV: 531 (Sadtler Research Laboratories Spectral Collection)
NMR: 270 (Varian Associates NMR Spectra Catalogue)
MASS: 891 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

2.13 Stability: Stable. Incompatible with strong oxidizing agents, organic materials, strong bases.

2.14 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Usage: Thymol is an antimicrobial compound which can increase the efficacy of antibiotics involving drug resistant bacteria. It inhibits growth and lactate production as well as reduces cellular glucose uptake within the bacteria.

4. Safety and Handling

4.1 Symbol: GHS05, GHS07, GHS09

4.1 Hazard Codes: C

4.1 Signal Word: Danger

4.1 Risk Statements: R22;R34;R51/53

4.1 Safety Statements: S26;S28;S36/37/39;S45;S61

4.1 Exposure Standards and Regulations: Thymol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
Thymol for use as a preservative only is an indirect food additive for use as a component of adhesives.

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: Log Kow = 3.30

4.3 Other Preventative Measures: Protect body from contamination. No eating in work areas.

4.4 Hazard Class: 8

4.4 Hazard Declaration: H302-H314-H411

4.4 Cleanup Methods: Collect with a brush onto a paper sheet. Place in an iron pan in hood. Burn the paper.

4.5 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
(a) Stuff a package with paper or flammable materials. Burn in a furnace. (b) Dissolve in a combustible solvent. Burn in a furnace by spraying the solution.

4.6 RIDADR: UN 3261

4.6 FirePotential: Flammable

4.7 Safety Profile: Poison by ingestion andintravenous routes. Moderately toxic bysubcutaneous route. Experimentalreproductive effects. Mutation datareported. An allergen. Incompatible withacetanilide. When heated to decompositionit emits acrid smoke and irritating fumes. AnFDA over-the-counter drug used as anantibacterial and antifungal agent.

4.8 Caution Statement: P273-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P391

4.8 Formulations/Preparations: /Present in/ Listerine Antiseptic
/Present in/ bensulfoid lotion
Technical, NF, reagent

4.9 Incompatibilities: Thymol is incompatible with iodine, alkalis, and oxidizing agents. Itliquefies, or forms soft masses, on trituration with acetanilide,antipyrine, camphor, monobromated camphor, chloral hydrate,menthol, phenol, or quinine sulfate. The antimicrobial activity ofthymol is reduced in the presence of proteins.

4.10 WGK Germany: 2

4.10 RTECS: XP2275000

4.10 Reactivities and Incompatibilities: Acetanilide; antipyrine; camphor; monobromated camphor; cholorohydrate; menthol; quinine sulfate; salol, urethene, spirit nitrous ether.

4.11 Report: Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.12 Safety: Safety Information of Thymol (CAS No.89-83-8):
Hazard Codes:?C,N
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); View all

4.13 Specification: ? ?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.

4.14 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1B

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H314 Causes severe skin burns and eye damage H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

89-83-8Total: 119 Synthesis Route

89-68-9 46 Suppliers

89-83-8 278 Suppliers

Literatures:
Ramanathan, Ahalya; Jimenez, Leslie S. Synthesis, 2010 , # 2 art. no. M04609SS, p. 217 - 220
Yield: ~82%

89-81-6 21 Suppliers

89-83-8 278 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 56, p. 1185,1187
Yield: ~%

89-82-7 48 Suppliers

89-83-8 278 Suppliers

Literatures:
Chemische Berichte, , vol. 60, p. 2339
Yield: ~%

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8. Other Information

8.0 Usage: Thymol is used as a preservative in halothane. It acts as an anesthetic, antiseptic in mouth wash, stabilizer in pharmaceutical preparations. It inhibits the growth and lactate production as well as reduces the uptake of cellular glucose within the bacteria. It is an active ingredient in toothpastes like euthymol. It is involved to control varroa mites and prevent fermentation and the growth of mold in bee colonies.

8.1 Merck: 14,9399

8.2 BRN: 1907135

8.3 毒性: GRAS(FEMA)。

8.4 Chemical Properties: white crystals or powder with a pungent odour

8.5 Chemical Properties: Thymol occurs as colorless or often large translucent crystals, or as a white crystalline powder with a herbal odor (aromatic and thymelike) and a pungent caustic taste.

8.6 Chemical Properties: Thymol is the main constituent of thyme and some origanum oils; it also occurs in many other essential oils. It forms colorless crystals (mp 51.5°C) with a spicy, herbal, slightly medicinal odor reminiscent of thyme. Thymol is prepared on a technical scale in a continuous high-temperature, high-pressure, liquid-phase, ortho-alkylation process, fromm-cresol and propylene, in the presence of activated aluminumoxide hydrate.
The crude thymol mixture, consisting of approximately 60% thymol, unreacted m-cresol (about 25%), and other (iso)propyl-substituted products, is separated by fractional distillation. Most of the by-products are recycled.
Thymol is used as a dry top note in lavender compositions, in men’s fragrances, and as a disinfectant in oral care products. It is also important as a startingmaterial for the production of racemic menthol.
Anethole is used in large quantities in the alcoholic beverage industry and in oral hygiene products. Some crude anethole is converted into anisaldehyde.; View all

8.7 Chemical Properties: Thymol has a characteristic herbaceous, warm and aromatic odor with a sweet, medicinal, spicy flavor

8.8 Occurrence: Reported in the essential oils of Monarda punctata, Satureia thymera, Origanum floribundum, Ocimum viride, Ocimum gratissimum and particularly in thyme (Thymus vulgaris L., T. capitatus, T. serpillum L.), where it is contained up to 50%. Also reported found in citrus peel oils, orange and tangerine juice, bilberry, cranberry, blueberry, papaya, blackberry, celery seed, chive, clove bud, cumin seed, ginger, peppermint oil, corn mint oil, Scotch spearmint oil, nutmeg, parsley, thyme, Gruyere cheese, parmesan cheese, romano cheese, white wine, black tea, plum, sweet and wild marjoram, fenugreek, mango, cardamom, dill herb and seed, licorice, lovage leaf, buckwheat, sweet corn, elder flower, cherimoya, rosemary, lemon balm, Spanish sage, anise hyssop, sweet grass oil, eucalyptus oil and mastic gum oil.

8.9 Uses: Thymol is an antimicrobial compound which can increase the efficacy of antibiotics involving drug resistant bacteria. It inhibits growth and lactate production as well as reduces cellular glucose upta ke within the bacteria.

8.10 Production Methods: Thymol is obtained from the volatile oil of thyme (Thymus vulgaris Linne′ (Fam. Labiatae)) by fractional distillation followed by extraction and recrystallization. Thyme oil yields about 20–30% thymol. Thymol may also be produced synthetically from pcymene, menthone, or piperitone, or by the interaction of m-cresol with isopropyl chloride.

8.11 Definition: thymol: A pungent-smelling colourless crystalline compound, C₁₀H₁₄O;m.p. 51°C. It occurs in various essentialoils, particularly oil of thyme,and can be made by using iron(III)chloride to oxidize piperitone (itselfextracted from eucalyptus oil). Itsantiseptic properties are exploited ingargles and mouthwashes.

8.12 Aroma threshold values: Detection: 86 to 790 ppb

8.13 Taste threshold values: Phenolic, medicinal, woody and spicy

8.14 General Description: Thymol is a monoterpene phenol derivative. It is a key volatile aroma constituent of the essential oil of plants such as thyme, basil, and oregano. It has strong antioxidant, antibacterial, anticarcinogenesis, anti-inflammatory, and antiseptic properties.

9. Computational chemical data

Molecular Weight: 150.21756g/mol
Molecular Formula: C₁₀H₁₄O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 150.104465066
Monoisotopic Mass: 150.104465066
Complexity: 120
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 20.2
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADQSAmAAyBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAeAwPAOwAABAAAIAACAAAIAABAAAAAAAAAAAA==

10. Question & Answer

What is Thymol Blue and How is it Used? Jul 31 2024
Overview Thymol Blue, also known as thymolsulfonphthalein, is a brown-green or red-purple crystalline powder with a peculiar odor. It is soluble in ethanol, turning yellow, soluble in dilute alkali so..
What are the Neuroprotective Properties of Thymol and its Potential Therapeutic Implications for Neurological Disorders? Jun 22 2024
General Description Thymol, a compound extracted from thyme oil, exhibits significant neuroprotective properties with potential therapeutic implications for neurological disorders. It shows promise in..
What are the applications and quality requirements of Thymol in pharmaceuticals? Dec 23 2023
Thymol (Vanillin) is a commonly used spice and food additive, and also plays an important role in the pharmaceutical field. Let's explore the applications of Thymol in pharmaceuticals and the related ..
What is Thymol Blue and How Does it Work? Aug 14 2023
Background and Overview Thymol Blue is a commonly used indicator in acid-base titration experiments. Its name "Bromothymol Blue" indicates that it is a bromine compound derived from thymol, a compound..

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Thymol