Terpinine-4-ol

Names

[ CAS No. ]:
562-74-3

[ Name ]:
Terpinine-4-ol

[Synonym ]:
3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)-
EINECS 209-235-5
1-Isopropyl-4-methyl-3-cyclohexen-1-ol
4-methyl-1-[1-methylethyl]-3-cyclohexen-1-ol
4-terpineol
4-terpinenol
terpineol-4
Terpine-4-ol
Terpene-4-ol
Terpinenol-4
p-menth-1-en-4-ol
(±)-4-Terpineol
Terpin-4-ol
1-(1-Methylethyl)-4-methyl-3-cyclohexen-1-ol
(±)-Terpinen-4-ol
Terpinen-4-ol
Terpinenolu-4
3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-
dl-4-Terpineol
4-Methyl-1-(1-methylethyl)-3-cyclohexene-1-ol
FEMA 2248
1-Isopropyl-4-methylcyclohex-3-en-1-ol
MFCD00001562

Biological Activity

[Description]:

Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Hart PH, et al. Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes. Inflamm Res. 2000 Nov;49(11):619-26.

[2]. Shapira S, et al. Terpinen-4-ol: A Novel and Promising Therapeutic Agent for Human Gastrointestinal Cancers. PLoS One. 2016 Jun 8;11(6):e0156540.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
209.0±0.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₈O

[ Molecular Weight ]:
154.249

[ Flash Point ]:
79.4±0.0 °C

[ Exact Mass ]:
154.135757

[ PSA ]:
20.23000

[ LogP ]:
2.99

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.485

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
Very slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OT0175110

CHEMICAL NAME :: para-Menth-1-en-4-ol

CAS REGISTRY NUMBER :: 562-74-3

BEILSTEIN REFERENCE NO. :: 1906603

LAST UPDATED :: 199701

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C10-H18-O

MOLECULAR WEIGHT :: 154.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,833,1982 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,833,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 8,433,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1016 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CCHCDE Zhonghua Jiehe He Huxixi Jibing Zazhi. Chinese Journal of Tuberculosis and Respiratory Diseases. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1978- Volume(issue)/page/year: 4(4),203,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 8,433,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 8,433,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 780 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: CKFRAY Ceskoslovenska Farmacie. (PNS-Ustredni Expedice a Dovoz Tisku, Kafkova 19, 160 00 Prague 6, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 8,433,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >2500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,833,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2137 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1167 (estimated) No. of Female Employees: 51 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ WGK Germany ]:
2

[ RTECS ]:
OT0175110

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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