• Name

  (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL

• EINECS
• CAS No. 22972-51-6
• Article Data35
• CAS DataBase
• Density 0.947 g/cm³
• Solubility 4.2g/L
• Melting Point
• Formula C₁₀H₁₆O
• Boiling Point 216.873 °C at 760 mmHg
• Molecular Weight 152.236
• Flash Point 86.957 °C
• Transport Information
• Appearance white solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Cyclohexen-1-ol,1-methyl-4-(1-methylethenyl)-, (1S-cis)-;(+)-(1S,4R)-p-Mentha-2,8-dien-1-ol;(+)-cis-p-Mentha-2,8-dien-1-ol;(+)-p-Mentha-2,8-dien-1-ol;(1S,4R)-p-Menth-2,8-dien-1-ol;cis-Isolimonenol;p-Mentha-2,8-dien-1-b-ol;
• PSA 20.23000
• LogP 2.27970

Synthetic route

C16H22O2S

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
With piperidine In dimethyl sulfoxide at 170℃; for 4h;	75%

1415961-21-5

(1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
at 180℃; under 1 Torr; Cope Elimination; Pyrolysis;	74%
With dihydrogen peroxide In ethanol; water at 150 - 162℃; Reflux; Schlenk technique; Glovebox; Inert atmosphere;	38.2 g

74756-11-9

(1S,2S,4R)-2-phenylseleninyl-p-menth-8-en-1-ol

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
In chloroform for 0.5h; Heating;	53%
In chloroform at 62℃; for 6h; Inert atmosphere;	512 g

6909-30-4

(1S,2R,4R)-limonene-1,2-epoxide

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
Stage #1: (1S,2R,4R)-limonene-1,2-epoxide With sodium tetrahydroborate; diphenyl diselenide for 2h; Heating; Stage #2: With dihydrogen peroxide for 7h; Heating; Further stages.;	31.6%
Multi-step reaction with 2 steps 1.1: H2O / 18 h / 150 °C 2.1: H2O2 / H2O / 18 h / 20 °C 2.2: 150 - 180 °C View Scheme
Multi-step reaction with 3 steps 1: H2O / 150 °C / sealed vessel 2: 30percent H2O2 / H2O 3: pyrolysis View Scheme

5989-27-5

D-limonene

A

52154-82-2

(1R,4R)-p-mentha-2,8-dien-1-ol

B

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
With oxygen; rose bengal In methanol at 0℃; for 8.5h; UV-irradiation;	A 5.3% B 13.4%
With air Erwaermen des Reaktionsprodukts mit wss. Natriumsulfit-Loesung;
(i) O2, MeOH, (irradiation), (ii) LiAlH4, Et2O; Multistep reaction;
(i) O2, rose bengal, MeOH, (irradiation), (ii) LiAlH4, Et2O; Multistep reaction;
With air Erwaermen des Reaktionsprodukts mit wss. Natriumsulfit-Loesung;

5989-27-5

D-limonene

A

99-48-9, 1197-06-4, 1197-07-5, 2102-58-1, 2102-59-2, 5157-78-8, 5503-11-7, 7632-16-8, 18383-51-2

(4R,6R)-carveol

B

18383-51-2

(-)-trans-carveol

C

52154-82-2

(1R,4R)-p-mentha-2,8-dien-1-ol

D

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

E

2102-62-7

p-Menthadiene-<1(7),8>-trans-ol-(2)

F

10374-04-6

p-Menthadiene<1(7),8>-cis-ol-(2)

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; air; zinc 5,10,15,20-tetraphenylporphyrin; triphenylphosphine In benzene for 3h; Irradiation; multistep reaction: photosensitized oxygenation of olefines;
With sodium tetrahydroborate; tetraphenylporphyrine; oxygen Product distribution; 1.) acetonitrile, irradiation, 2.) methanol; other sensitizers;	A 5 % Chromat. B 7 % Chromat. C 9 % Chromat. D 40 % Chromat. E 16 % Chromat. F 23 % Chromat.
With oxygen; fullerene-C60 In toluene at 0 - 10℃; for 4h; Product distribution; Irradiation; other sensitizer in other solvent;

...Expand

138-86-3

limonene.

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
With oxygen Irradiation;

5989-27-5

D-limonene

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
With oxygen Irradiation;
Multi-step reaction with 4 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / -5 - 20 °C 2: water / 18 h / 20 °C / Reflux 3: dihydrogen peroxide / water; acetonitrile / 2 h / 20 °C / Cooling with ice 4: 180 °C / 1 Torr / Pyrolysis View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C 2.1: sodium tetrahydroborate / ethanol / 1 h / 8 °C / Inert atmosphere 2.2: 4 h / 8 - 80 °C / Inert atmosphere 3.1: dihydrogen peroxide / ethanol; tetrahydrofuran / 6 h / 6 - 20 °C / Inert atmosphere 4.1: chloroform / 6 h / 62 °C / Inert atmosphere View Scheme

(+)-trans-N.N-Dimethylamino-2-p-menthen-8-ol-1-N-oxyd

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
at 140℃;

(1S,2S,4R)-4-Isopropenyl-1-methyl-2-nitroso-cyclohexanol

22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

Conditions

Conditions	Yield
pyrolysis; Yield given;

trans-Mentha-2,8-dien-1-ol Specification