CAS No.562-74-3,3-Cyclohexen-1-ol,4-methyl-1-(1-methylethyl)- Suppliers

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Basic Information

Molecular Structure:
CAS No.:	562-74-3
Name:	3-Cyclohexen-1-ol,4-methyl-1-(1-methylethyl)-
Article Data:	30
Cas Database

Formula:	C₁₀H₁₈O
Molecular Weight:	154.252
Synonyms:	p-Menth-1-en-4-ol(8CI);1-(1-Methylethyl)-4-methyl-3-cyclohexen-1-ol;1-Isopropyl-4-methylcyclohex-3-en-1-ol;1-Terpinen-4-ol;4-Carvomenthenol;4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol;4-Methyl-1-(1-methylethyl)-3-cyclohexene-1-ol;4-Methyl-1-isopropyl-3-cyclohexen-1-ol;4-Terpinenol;4-Terpineol;Melaleucol;NSC 147749;Terpin-4-ol;Terpinene-4-ol;Terpineol-4;dl-4-Terpineol;
EINECS:	209-235-5
Density:	0.933 g/cm³
Melting Point:	137-188 °C
Boiling Point:	208.999 °C at 760 mmHg
Flash Point:	79.444 °C
Solubility:	Slightly soluble in water, soluble in alcohol and oil
Appearance:	colourless or pale yellow liquid
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38
Safety:	26-36-37/39
Transport Information:	N/A
PSA:	20.23000
LogP:	2.50370

Synthetic route

: 3419-02-1
4-methyl-1-isopropenylcyclohex-3-en-1-ol

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With hydrogen In water; ethyl acetate at 50℃; under 75.0075 Torr; for 5h; Solvent; Concentration; Temperature; Large scale;	97.8%

: 125816-48-0
(1-Isopropyl-4-methyl-cyclohex-3-enyloxymethoxy)-dimethyl-(1,1,2-trimethyl-propyl)-silane

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2.5h; Product distribution; Ambient temperature; cleavage with Et4NF in MeCN; cleavage of acetals with tetraalkylammonium fluoride salts; protection and deprotection of alcohols with chloromethoxysilanes;	78%

: 4584-23-0
2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene

A: 562-74-3
TERPINEN-4-OL

B: 3419-02-1
4-methyl-1-isopropenylcyclohex-3-en-1-ol

Conditions

Conditions	Yield
With hydrogen In ethyl acetate at 25 - 125℃; under 3750.38 Torr; for 24h; Temperature; Reagent/catalyst; Solvent; Time; Autoclave; Inert atmosphere; Overall yield = 82.7 %;	A 8.3% B 74.4%

: 4584-23-0
2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene

A: 562-74-3
TERPINEN-4-OL

B: 98-55-5
terpineol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 8h; Ambient temperature;	A 67% B 22%
With lithium In ethylenediamine for 0.5h;	A 36% B 60%

: 105273-31-2
Acetic acid (Z)-3,7-dimethyl-6-oxo-oct-2-enyl ester

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With samarium diiodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 3h; Heating;	62%

: 2009-00-9, 10408-16-9, 15826-80-9, 3387-41-5
sabinene

A: 562-74-3
TERPINEN-4-OL

B: 3484-42-2
2-methyl-5-(1-methylethyl)-(1α,2α,5α)-bicyclo[3.1.0]hexan-2-ol

C: trans-sabinene hydrate

Conditions

Conditions	Yield
With Penicillium paxilli In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 56% B 3% C 13%
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Reagent/catalyst; Microbiological reaction;	A 30% B 21% C 17%

...Expand

: 470-67-7
1,4-cineole

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With n-butyllithium; potassium tert-butylate In hexane at 60℃; for 40h;	50%

: 4584-23-0
2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene

A: 586-62-9
Terpinolene

B: 1197-01-9
p-cymene-8-ol

C: 562-74-3
TERPINEN-4-OL

D: 98-55-5
terpineol

Conditions

Conditions	Yield
With sodium In tetrahydrofuran at 65℃; for 12h;	A 4% B 16% C 48% D 26%

...Expand

: 2009-00-9, 3387-41-5, 10408-16-9, 15826-80-9
(±)-sabinene

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With formic acid Verseifen des Formiats; dextrorotatory terpinenol-(4);

: 2009-00-9, 3387-41-5, 10408-16-9, 15826-80-9
(±)-sabinene

A: 562-74-3
TERPINEN-4-OL

B: 91008-90-1
terpin-4-ol

Conditions

Conditions	Yield
With sulfuric acid dextrorotatory terpinenol-(4);

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Consensus Reports

4-TERPINEOL is reported in EPA TSCA Inventory.

Specification

The Terpinen-4-ol, with the CAS registry number 562-74-3, is also known as 4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol. It belongs to the product categories of Biochemistry; Terpenes; Terpenes (Others); Monocyclic Monoterpenes; Intermediates & Fine Chemicals; Pharmaceuticals; Alphabetical Listings; C-D Flavors and Fragrances; Certified Natural Products; Flavors and Fragrances. Its EINECS number is 209-235-5. This chemical's molecular formula is C₁₀H₁₈O and molecular weight is 154.25. What's more, its systematic name is 1-Isopropyl-4-methyl-3-cyclohexen-1-ol. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Natural Product; (3)Skin / Eye Irritant. This chemical is mainly the primary active ingredient of tea tree oil. It is also the compound of highest concentration in the essential oil of nutmeg. It shows antioxidant effects and is an antiseptic.

Physical properties of Terpinen-4-ol are: (1)ACD/LogP: 2.538; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.54; (4)ACD/LogD (pH 7.4): 2.54; (5)ACD/BCF (pH 5.5): 50.01; (6)ACD/BCF (pH 7.4): 50.01; (7)ACD/KOC (pH 5.5): 572.50; (8)ACD/KOC (pH 7.4): 572.50; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 20.23 Å²; (13)Index of Refraction: 1.485; (14)Molar Refractivity: 47.339 cm³; (15)Molar Volume: 165.26 cm³; (16)Polarizability: 18.766×10^-24cm³; (17)Surface Tension: 33 dyne/cm; (18)Density: 0.933 g/cm³; (19)Flash Point: 79.444 °C; (20)Enthalpy of Vaporization: 51.794 kJ/mol; (21)Boiling Point: 208.999 °C at 760 mmHg; (22)Vapour Pressure: 0.048 mmHg at 25°C.

Preparation: this chemical can be prepared by acetic acid 3,7-dimethyl-6-oxo-oct-2-enyl ester by heating. This reaction will need reagent SmI₂ and solvent tetrahydrofuran with the reaction time of 3 hours. This reaction will also need catalyst Pd(PPh₃)₄. The yield is about 62%.

Terpinen-4-ol can be prepared by acetic acid 3,7-dimethyl-6-oxo-oct-2-enyl ester by heating

Uses of Terpinen-4-ol: it can be used to produce triethyl-(1-isopropyl-4-methyl-cyclohex-3-enyloxy)-silane at the temperature of 25 °C. It will need reagent PyH(+)·OTf(-) and solvent tetrahydrofuran with the reaction time of 10 min. The yield is about 99%.

Terpinen-4-ol can be used to produce triethyl-(1-isopropyl-4-methyl-cyclohex-3-enyloxy)-silane at the temperature of 25 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: CC1=CCC(CC1)(C(C)C)O
(2)Std. InChI: InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
(3)Std. InChIKey: WRYLYDPHFGVWKC-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intramuscular	780mg/kg (780mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.
mouse	LD50	oral	1016mg/kg (1016mg/kg)		Zhonghua Jiehe He Huxixi Jibing Zazhi. Chinese Journal of Tuberculosis and Respiratory Diseases. Vol. 4(4), Pg. 203, 1981.
mouse	LD50	subcutaneous	750mg/kg (750mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.
rabbit	LD50	skin	> 2500mg/kg (2500mg/kg)		Food and Chemical Toxicology. Vol. 20, Pg. 833, 1982.
rat	LD50	intramuscular	1500mg/kg (1500mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	Cesko-Slovenska Farmacie. Vol. 8, Pg. 433, 1959.
rat	LD50	oral	1300mg/kg (1300mg/kg)		Food and Chemical Toxicology. Vol. 20, Pg. 833, 1982.