Terpinen-4-ol supplier | CasNO.562-74-3

Name
Terpinen-4-ol
EINECS 209-235-5
CAS No. 562-74-3
Article Data30
CAS DataBase
Density 0.933 g/cm³
Solubility Slightly soluble in water, soluble in alcohol and oil
Melting Point 137-188 °C
Formula C₁₀H₁₈O
Boiling Point 208.999 °C at 760 mmHg
Molecular Weight 154.252
Flash Point 79.444 °C
Transport Information
Appearance colourless or pale yellow liquid
Safety 26-36-37/39
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
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;
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);

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

A: 1195-32-0
1-methyl-4-isopropenylbenzene

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

C: 99-87-6
4-methylisopropylbenzene

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

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 66℃; for 7.5h; Further byproducts given. Title compound not separated from byproducts;

...Expand

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

A: 1195-32-0
1-methyl-4-isopropenylbenzene

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

C: 99-87-6
4-methylisopropylbenzene

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

E: 53312-55-3
p-mentha-1,4-dien-8-ol

F: 82538-84-9
1-(1'-hydroxy-1'-methylethyl)-4-methylcyclohexa-1,3-diene

Conditions

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 27℃; for 0.75h; Product distribution; var. solvents and temp.;

...Expand

: 27621-71-2
1,4-dichloro-p-menthane

KOH-solution: KOH-solution

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

B: 586-81-2
γ-terpineol

Conditions

Conditions	Yield
at 100℃; trans-form;

...Expand

: 7664-93-9
sulfuric acid

: 563-34-8, 2867-05-2, 3917-48-4, 75715-79-6
α-thujene

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
levorotatory form;

dextrorotatory sabinene hydrate: dextrorotatory sabinene hydrate

: 562-74-3
TERPINEN-4-OL

Conditions

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

: 91008-90-1
terpin-4-ol

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

B 1.4-oxido-p-menthane: 1.4-oxido-p-menthane

Conditions

Conditions	Yield
With oxalic acid inactive terpinenol-(4);

: 25570-95-0
1,4-dichloro-trans-p-menthane

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

B terpinene: terpinene

Conditions

Conditions	Yield
With potassium hydroxide at 50 - 100℃; inactive terpinenol-(4);

: 470-67-7
1,4-cineole

: 138-86-3
limonene.

: 562-74-3
TERPINEN-4-OL

Conditions

Conditions	Yield
With anthracene; sodium In water

: 763-10-0
geranyl diphosphate

A: 106-24-1
Geraniol

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

C: 471-84-1, 2623-54-3, 7378-37-2, 116724-26-6
fenchene

Conditions

Conditions	Yield
With 6His-tagged Pseudomonas fluorescens PfO-1 Pfl_1841 2-methylenebornane synthase In pentane at 30℃; for 12h; pH=6.7; Kinetics; Concentration; aq. buffer; Enzymatic reaction;	A 6 %Chromat. B 5 %Chromat. C 52 %Chromat.

...Expand

: 562-74-3
TERPINEN-4-OL

: 18663-30-4
Benz-phenylimidsaeure-triaethylsilylester

: 1-(triethylsiloxy)-1-isopropyl-4-methyl-3-cyclohexane

Conditions

Conditions	Yield
With pyridinium triflate In tetrahydrofuran at 25℃; for 0.166667h;	99%

: 562-74-3
TERPINEN-4-OL

: 404392-70-7
tert-butyldimethylsilyl N-phenylbenzimidate

: 1-(tert-butyldimethylsilyloxy)-1-isopropyl-4-methyl-3-cyclohexene

Conditions

Conditions	Yield
With pyridinium triflate In tetrahydrofuran at 50℃; for 2.5h;	96%

: 562-74-3
TERPINEN-4-OL

: 96622-71-8
C16H19NOSi

: (1-isopropyl-4-methyl-cyclohex-3-enyloxy)-trimethyl-silane

Conditions

Conditions	Yield
With pyridinium triflate In tetrahydrofuran at 25℃; for 0.0833333h;	95%

: 562-74-3
TERPINEN-4-OL

: 53742-62-4
anilino(tert-butyldimethyl)silane

: 1-(tert-butyldimethylsilyloxy)-1-isopropyl-4-methyl-3-cyclohexene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 3h;	92%

: 110-87-2
3,4-dihydro-2H-pyran

: 562-74-3
TERPINEN-4-OL

: C15H26O2

Conditions

Conditions	Yield
With N.N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea at 50℃; for 51h;	92%

: 562-74-3
TERPINEN-4-OL

: 18106-48-4
1,1,1-triethyl-N-phenylsilanamine

: 1-(triethylsiloxy)-1-isopropyl-4-methyl-3-cyclohexane

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 0.5h;	91%

: 562-74-3
TERPINEN-4-OL

: 108-24-7
acetic anhydride

: 4821-04-9
α-terpinenyl acetate

Conditions

Conditions	Yield
With C12H8N2*2CH4O3S at 40℃; for 5h;	89%
With sodium acetate In xylene
With pyridine In dichloromethane Acetylation;

: 562-74-3
TERPINEN-4-OL

: 74-95-3
1,2-dibromomethane

: 3-isopropyl-6-methylbicyclo[4.1.0]heptan-3-ol

Conditions

Conditions	Yield
Stage #1: TERPINEN-4-OL With tert-butylmagnesium chloride In tetrahydrofuran; diethyl ether Cooling; Inert atmosphere; Stage #2: 1,2-dibromomethane With tert-butylmagnesium chloride In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere; optical yield given as %de;	89%
With tert-butylmagnesium chloride In diethyl ether at 25℃; for 16h;	85%

: 562-74-3
TERPINEN-4-OL

: 2322-45-4
2-bromo-2-methyl-N-phenylpropanamide

: 2-((1-isopropyl-4-methylcyclohex-3-en-1-yl)oxy)-2-methyl-N-phenylpropanamide

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 18h; Inert atmosphere;	82%
With potassium phosphate; copper(I) bromide dimethylsulfide complex; tricyclohexylphosphine In acetonitrile at 80℃; for 24h;	48%

: 562-74-3
TERPINEN-4-OL

: 125816-34-4
1-chloro-3,3,4,4,5-pentamethyl-2-oxa-3-silahexane

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 45h; Ambient temperature;	80%

: 562-74-3
TERPINEN-4-OL

: (1R,3R,6S)-3-Isopropyl-6-methyl-7-oxa-bicyclo[4.1.0]heptan-3-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; dicyclohexyl-carbodiimide In water Ambient temperature; other reagent: H2O2/KHCO3/benzonitrile;	80%

: 562-74-3
TERPINEN-4-OL

: 1753-42-0
1-isopropyl-4-methylcyclohexane-1,4-diol

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; diastereoselective reaction;	76%

: 562-74-3
TERPINEN-4-OL

: 22621-68-7
2-hydroxy-1,4-cineole

Conditions

Conditions	Yield
With dihydrogen peroxide In chloroform at 25℃; for 0.5h; Concentration; Solvent; Temperature;	70.1%

: 562-74-3
TERPINEN-4-OL

: 74-88-4
methyl iodide

: 94281-60-4
4-isopropyl-4-methoxy-1-methylcyclohex-1-ene

Conditions

Conditions	Yield
With potassium tert-butylate In diethyl ether at 20℃; for 72h; Schlenk technique;	60%

: 562-74-3
TERPINEN-4-OL

: 2873-29-2
D-glucal triacetate

: 1619941-96-6
α-terpinyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Conditions

Conditions	Yield
With zinc dibromide In chloroform at 72℃; for 0.916667h; Ferrier Carbohydrate Rearrangement; Microwave irradiation; stereoselective reaction;	56%

: 562-74-3
TERPINEN-4-OL

: 616-38-6
carbonic acid dimethyl ester

: 1262126-86-2
methyl 4-terpinyl carbonate

Conditions

Conditions	Yield
Stage #1: carbonic acid dimethyl ester With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 20℃; Stage #2: TERPINEN-4-OL for 89h; Reflux; chemoselective reaction;	55%

: 562-74-3
TERPINEN-4-OL

A: 3,4-cis-Epoxy-1-isopropyl-4-methylcyclohexan-1-ol

B: 98109-59-2
para-menthane-1,2,4-triol

Conditions

Conditions	Yield
With 3-Methylpyrazole; dihydrogen peroxide; methyltrioxorhenium(VII) at 10 - 20℃; for 2h;	A n/a B 42%

: 562-74-3
TERPINEN-4-OL

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 99049-84-0, 99049-85-1
1-p-Menthen-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid

Conditions

Conditions	Yield
With molecular sieve; silver silicate In dichloromethane for 48h; Ambient temperature;	21%

: 562-74-3
TERPINEN-4-OL

: 25570-96-1
1,4-dibromo-p-menthane

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid trans-form;

: 562-74-3
TERPINEN-4-OL

: 27621-71-2
1,4-dichloro-p-menthane

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid trans-form;

: 562-74-3
TERPINEN-4-OL

: 25570-95-0
1,4-dichloro-trans-p-menthane

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid

: 562-74-3
TERPINEN-4-OL

: 3239-02-9
cis-p-menthan-4-ol

Conditions

Conditions	Yield
With nickel at 125 - 130℃; under 5884.06 Torr; Hydrogenation;
With (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen In toluene at -196.15 - 25℃; under 3040.2 Torr; for 4h; Reagent/catalyst; Sealed tube; diastereoselective reaction;	n/a
With C54H57F3N4O6RuS; hydrogen In dichloromethane at 80℃; under 37503.8 Torr; for 13h; Reagent/catalyst; Inert atmosphere; Sealed tube;
With hydrogen In toluene at 80℃; under 2250.23 Torr; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature; Autoclave; diastereoselective reaction;	n/a

Terpinen-4-ol Consensus Reports

4-TERPINEOL is reported in EPA TSCA Inventory.

Terpinen-4-ol 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.

Product Name

Terpinen-4-ol

Synthetic route

Terpinen-4-ol Consensus Reports

Terpinen-4-ol Specification

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