Product Name

  • Name

    (-)-alpha-Terpineol

  • EINECS 233-986-8
  • CAS No. 10482-56-1
  • Article Data20
  • CAS DataBase
  • Density 0.93 g/cm3
  • Solubility 2.23g/L at 20℃
  • Melting Point 31-35 °C(lit.)
  • Formula C10H18O
  • Boiling Point 217.5 °C at 760 mmHg
  • Molecular Weight 154.252
  • Flash Point 89.4 °C
  • Transport Information
  • Appearance Clear, colorless liquid.
  • Safety 26-36-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 10482-56-1 ((-)-alpha-Terpineol)
  • Hazard Symbols IrritantXi
  • Synonyms 3-Cyclohexene-1-methanol,α,α,4-trimethyl-, (S)-;p-Menth-1-en-8-ol, (S)-(-)-(8CI);(S)-(-)-Terpineol;(S)-(-)-α-Terpineol;(S)-α,α,4-Trimethyl-3-cyclohexene-1-methanol;(S)-a-Terpineol;l-α-Terpineol;α-Terpineol, (-)-;
  • PSA 20.23000
  • LogP 2.50370

Synthetic route

1-methyl-1-(4-methyl-3-cyclohexenyl)ethyl hydroperoxide
613241-83-1

1-methyl-1-(4-methyl-3-cyclohexenyl)ethyl hydroperoxide

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 0.0833333h;94%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

benzyl (1S)-4-methylcyclohex-3-ene-1-carboxylate
245680-35-7

benzyl (1S)-4-methylcyclohex-3-ene-1-carboxylate

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 13h;86%
N-<(R)-1-phenylethyl>-O-<(3S,4S)-8-hydroxy-1-p-menthen-3-yl>urethane
119614-28-7

N-<(R)-1-phenylethyl>-O-<(3S,4S)-8-hydroxy-1-p-menthen-3-yl>urethane

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With sodium; lithium In various solvent(s) at 0℃;35%
(-)-α-pinene
7785-26-4

(-)-α-pinene

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With formic acid Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge;
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With nitric acid; potassium nitrate Behandeln des Reaktionsprodukts mit wss. Ammoniak und Zink;

A

δ-terpineol
7299-42-5

δ-terpineol

B

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

C

(+)-8-bromo-α-fenchol
146203-05-6

(+)-8-bromo-α-fenchol

Conditions
ConditionsYield
With N-Bromosuccinimide; acetic acid; zinc 1.) acetone, water, 30 min, 2.) ether, 30 min; Multistep reaction;
hydrogen sulfate of (-)-bornylamine

hydrogen sulfate of (-)-bornylamine

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With water; sodium nitrite unter Kuehlung;
H4fe(CN)6

H4fe(CN)6

A

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

B

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

C

(-)-isofenchylamine

(-)-isofenchylamine

Conditions
ConditionsYield
anschl. Erhitzen mit 10prozentig. wss. KOH auf 160grad;
diethyl ether
60-29-7

diethyl ether

N-(R)-(+)-bornylamine
37606-04-5

N-(R)-(+)-bornylamine

water
7732-18-5

water

sodium nitrite

sodium nitrite

A

camphene
5794-04-7

camphene

B

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
das Hydrogensulfat reagiert;
(4S)-α-terpineol 8-O-β-D-glucopyranoside
89616-07-9

(4S)-α-terpineol 8-O-β-D-glucopyranoside

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
With water; β-glucosidase at 37℃; for 24h; Hydrolysis; Enzymatic reaction;1.4 mg
(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dioxygen; bis(1-morpholinocarbamoyl-4,4-dimethyl-1,3-pentanedionato)Co; triethylsilane / 1,2-dichloro-ethane / 24 h / 20 °C
1.2: 8 percent / HCl / methanol; H2O / 0.08 h
2.1: 94 percent / triphenylphosphine / CH2Cl2 / 0.08 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: dioxygen; bis(1-morpholinocarbamoyl-4,4-dimethyl-1,3-pentanedionato)Co; triethylsilane / 1,2-dichloro-ethane / 1 h / 20 °C
1.2: 36 percent / HCl / methanol; H2O / 0.08 h
2.1: 94 percent / triphenylphosphine / CH2Cl2 / 0.08 h / 0 °C
View Scheme
Stage #1: (-)-(S)-limonene With mercury(II) diacetate In tetrahydrofuran; water
Stage #2: With sodium tetrahydroborate; sodium hydroxide
(4S)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside

(4S)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5.5 mg / tannase, Aspergillus oryzae; H2O / 3 h / 30 °C / Enzymatic reaction
2: 1.4 mg / β-glucosidase; H2O / 24 h / 37 °C / Enzymatic reaction
View Scheme
6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one
87791-00-2

6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LiAlH4 / 1.) Et2O, room temperature, 24 h, 2.) benzene, room temperature, 24 h
2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) THF, hexane, -78 deg C, 30 min
3: 35 percent / Li, Na / various solvent(s) / 0 °C
View Scheme
(+/-)-trans-1-p-menthene-3,8-diyl carbonate

(+/-)-trans-1-p-menthene-3,8-diyl carbonate

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) THF, hexane, -78 deg C, 30 min
2: 35 percent / Li, Na / various solvent(s) / 0 °C
View Scheme
nerol β-D-glucopyranoside
22850-14-2

nerol β-D-glucopyranoside

A

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

B

Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

Conditions
ConditionsYield
With water pH=2.5;
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: silver(l) oxide / diethyl ether / 220 h / 20 °C / Darkness
2: water / pH 2.5
View Scheme
α-D-glucopyranose peracetylate
604-68-2

α-D-glucopyranose peracetylate

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic anhydride; hydrogen bromide / water / 3 h / Cooling with ice
2: silver(l) oxide / diethyl ether / 220 h / 20 °C / Darkness
3: water / pH 2.5
View Scheme
4-(allyloxy)-4-oxobutanoic acid
3882-09-5

4-(allyloxy)-4-oxobutanoic acid

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Succinic acid allyl ester 1-methyl-1-(4-methylcyclohex-3-enyl)ethyl ester

Succinic acid allyl ester 1-methyl-1-(4-methylcyclohex-3-enyl)ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; under 11250900 Torr; for 24h;95%
methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

Succinic acid methyl ester 1-methyl-1-(4-methylcyclohex-3-enyl)ethyl ester

Succinic acid methyl ester 1-methyl-1-(4-methylcyclohex-3-enyl)ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; under 11250900 Torr; for 24h;92%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

2-bromo-4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol

2-bromo-4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetone87%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

(1S,2S,5S)-2,6,6-trimethyl-7-oxa-bicyclo<3.1.1>octan-2-ol

(1S,2S,5S)-2,6,6-trimethyl-7-oxa-bicyclo<3.1.1>octan-2-ol

Conditions
ConditionsYield
With thallium(III) acetate In water; acetic acid for 1h; Ambient temperature;86%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

2-((S)-6-Methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-propan-2-ol

2-((S)-6-Methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-propan-2-ol

Conditions
ConditionsYield
With Oxone; acetyl methyl β-cyclodextrin; sodium hydrogencarbonate; edetate disodium In acetonitrile at 20℃; for 0.666667h;85%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

4-(2-chloro-2-propyl)-1-methyl-1-cyclohexene

4-(2-chloro-2-propyl)-1-methyl-1-cyclohexene

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 5℃; Inert atmosphere;81.64%
(3R-cis)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone
149107-92-6

(3R-cis)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

α-terpeneyl N-benzoyl-(2'R,3'S)-phenylisoserine ester

α-terpeneyl N-benzoyl-(2'R,3'S)-phenylisoserine ester

Conditions
ConditionsYield
Stage #1: (-)-(S)-α-terpineol With lithium hexamethyldisilazane In tetrahydrofuran at -45℃; for 1h;
Stage #2: (3R-cis)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone In tetrahydrofuran at 0℃; for 2h;
Stage #3: With water; acetic acid In tetrahydrofuran at 0℃; for 3h;
80%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(S,S)-α-methoxy-α-(((trifluoromethyl)phenyl)acetyl) ester (R)-terpineol

(S,S)-α-methoxy-α-(((trifluoromethyl)phenyl)acetyl) ester (R)-terpineol

Conditions
ConditionsYield
With dmap In 1,2-dichloro-ethane at 70℃; for 18h;76%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

dihydro-5,5-dimethyl-4-(3-oxobutyl)furan-2(3H)-one

dihydro-5,5-dimethyl-4-(3-oxobutyl)furan-2(3H)-one

Conditions
ConditionsYield
With sodium periodate; ruthenium(III) chloride trihydrate In tetrachloromethane; water; acetonitrile at 0 - 20℃;68%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

eucalyptol

eucalyptol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; Inert atmosphere;67%
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

(S)-trimethyl(2-(4-methylcyclohex-3-enyl)propan-2-yloxy)silane
57304-99-1

(S)-trimethyl(2-(4-methylcyclohex-3-enyl)propan-2-yloxy)silane

Conditions
ConditionsYield
With 1% Au/TiO2 In ethyl acetate at 55℃; for 3h;62%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

(S)-4-(2-azidopropan-2-yl)-1-methylcyclohex-1-ene

(S)-4-(2-azidopropan-2-yl)-1-methylcyclohex-1-ene

Conditions
ConditionsYield
With tris(pentafluorophenyl)borane monohydrate; trimethylsilylazide In nitromethane at 23℃; for 1h; Sealed tube;58%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

C15H26O2

C15H26O2

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 0.5h; Heating;52%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

benzyl chloroformate
501-53-1

benzyl chloroformate

benzyl ((5S)-5-(2-hydroxypropan-2-yl)-2-methylcyclohexyl)carbamate

benzyl ((5S)-5-(2-hydroxypropan-2-yl)-2-methylcyclohexyl)carbamate

Conditions
ConditionsYield
Stage #1: (-)-(S)-α-terpineol With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; ammonium carbonate; 2-amino-benzenethiol In dichloromethane; acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;
Stage #2: benzyl chloroformate
51%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate
219547-77-0

t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate

C15H27NO3

C15H27NO3

Conditions
ConditionsYield
Stage #1: (-)-(S)-α-terpineol With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Metallation;
Stage #2: t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate In tetrahydrofuran at -78 - 20℃; Substitution; Further stages.;
50%
4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

1-cyano-4-[1-methyl-1-(4-methylcyclohex-3-enyl)ethoxy]benzene

1-cyano-4-[1-methyl-1-(4-methylcyclohex-3-enyl)ethoxy]benzene

Conditions
ConditionsYield
With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 20h; Inert atmosphere;17%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

A

5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone
7712-46-1

5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone

B

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxaldehyde
56197-78-5

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With air; GifIV = pyridine; acetic acid; iron(II) chloride; zincA 6.3%
B 1.4%
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With pyrographite at 200℃;
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

homoterpenylmethylketone
4436-81-1

homoterpenylmethylketone

Conditions
ConditionsYield
With jones reagent
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

(-)-(1R,2R,4S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane-6-ol
103665-39-0

(-)-(1R,2R,4S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane-6-ol

Conditions
ConditionsYield
With dioxyphthalic acid
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

A

(-)-trans-sobrerol
71697-84-2

(-)-trans-sobrerol

B

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-methanol
19894-91-8

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-methanol

C

(4R,6R)-6-hydroxy-4-(1-hydroxyisopropyl)-1-methylcyclohexene
772-36-1

(4R,6R)-6-hydroxy-4-(1-hydroxyisopropyl)-1-methylcyclohexene

Conditions
ConditionsYield
With Nicotiana tabacum Product distribution; effect of incubation time;
With sodium phosphate buffer; Nicotiana tabacum; oxygen; NADPH at 30℃; for 2h; Product distribution; hydroxylation, various substrartes, hydroxylase activity under different reaction conditions;
(-)-(S)-α-terpineol
10482-56-1

(-)-(S)-α-terpineol

2-((1S,3R,4R)-3,4-Dibromo-4-methyl-cyclohexyl)-propan-2-ol

2-((1S,3R,4R)-3,4-Dibromo-4-methyl-cyclohexyl)-propan-2-ol

Conditions
ConditionsYield
With bromine In diethyl ether for 6h; Ambient temperature;

(-)-alpha-Terpineol Specification

The 3-Cyclohexene-1-methanol,α,α,4-trimethyl-, (1S)-, with the CAS registry number 10482-56-1, is also known as (L)-alpha-Terpineol. Its EINECS registry number is 233-986-8. This chemical's molecular formula is C10H18O and molecular weight is 154.24932. Its IUPAC name is called 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol. What's more, the product should be sealed and stored in cool and dry place.

Physical properties of 3-Cyclohexene-1-methanol,α,α,4-trimethyl-, (1S)-: (1)ACD/LogP: 2.79; (2)#H bond acceptors: 1; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 2; (5)Index of Refraction: 1.482; (6)Molar Refractivity: 47.07 cm3; (7)Molar Volume: 164.9 cm3; (8)Surface Tension: 33.2 dyne/cm; (9)Density: 0.934 g/cm3; (10)Flash Point: 89.4 °C; (11)Enthalpy of Vaporization: 52.78 kJ/mol; (12)Boiling Point: 217.5 °C at 760 mmHg; (13)Vapour Pressure: 0.0283 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

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

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