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| CAS No.: | 5986-55-0 |
|---|---|
| Name: | Patchouli alcohol |
| Molecular Structure: | |
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| Formula: | C15H26O |
| Molecular Weight: | 222.371 |
| Synonyms: | 1,6-Methanonaphthalen-1(2H)-ol,octahydro-4,8a,9,9-tetramethyl-, [1R-(1a,4b,4aa,6b,8aa)]-;1,6-Methanonaphthalen-1b(2H)-ol, 3,4,4ab,5,6b,7,8,8a-octahydro-4a,8ab,9,9-tetramethyl- (8CI);Patchouli alcohol (6CI,7CI);(-)-Patchouli alcohol;(-)-Patchoulol;Patchoulol; |
| EINECS: | 227-807-2 |
| Density: | 1.001 g/cm3 |
| Melting Point: | 56°; mp (racemate) 39-40° (Danishevsky, Dumas); mp 46-47° (Mirrington, Schmalzl) |
| Boiling Point: | 287.443 °C at 760 mmHg |
| Flash Point: | 120.179 °C |
| Solubility: | 41.8mg/L at 24℃ |
| Safety: | 24/25 |
| PSA: | 20.23000 |
| LogP: | 3.60980 |
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- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal at 20℃; for 12h; | 99% |
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 175 - 220℃; |
- 874747-37-2
(1S,4R,6R)-6-(2-hydroxybut-3-en-2-yl)-1,3,3-trimethylbicyclo[2.2.2]octan-2-one
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 2: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 3: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 874747-39-4
(1S,4R,6R)-6-[2-(methoxymethyloxy)but-3-en-2-yl]-1,3,3-trimethylbicyclo[2.2.2]octan-2-one
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 2: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 874747-38-3
(1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1.1: oxalyl chloride / benzene / 2 h / 20 °C 2.1: DMAP / benzene / 1 h / Heating 3.1: 20 mg / AIBN; tributyltin hydride / benzene / 5 h / Heating 4.1: ozone; NaHCO3 / methanol; CH2Cl2 4.2: 93 percent / dimethyl sulfide / methanol; CH2Cl2 / 10 h / 20 °C 5.1: 82 percent / tetrahydrofuran / 1 h / 0 °C 6.1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 7.1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 8.1: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1.1: DMAP / benzene / 1 h / Heating 2.1: 20 mg / AIBN; tributyltin hydride / benzene / 5 h / Heating 3.1: ozone; NaHCO3 / methanol; CH2Cl2 3.2: 93 percent / dimethyl sulfide / methanol; CH2Cl2 / 10 h / 20 °C 4.1: 82 percent / tetrahydrofuran / 1 h / 0 °C 5.1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 6.1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 7.1: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1.1: 20 mg / AIBN; tributyltin hydride / benzene / 5 h / Heating 2.1: ozone; NaHCO3 / methanol; CH2Cl2 2.2: 93 percent / dimethyl sulfide / methanol; CH2Cl2 / 10 h / 20 °C 3.1: 82 percent / tetrahydrofuran / 1 h / 0 °C 4.1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 5.1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 6.1: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 132060-03-8
(-)-(1S,4R,6S)-6-isopropenyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1.1: ozone; NaHCO3 / methanol; CH2Cl2 1.2: 93 percent / dimethyl sulfide / methanol; CH2Cl2 / 10 h / 20 °C 2.1: 82 percent / tetrahydrofuran / 1 h / 0 °C 3.1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 4.1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 5.1: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 132152-67-1
(-)-(1S,4R,6R)-6-acetyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 82 percent / tetrahydrofuran / 1 h / 0 °C 2: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 3: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 4: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
- 733001-15-5
(-)-(1S,2R,4S,8S)-8-isopropenyl-4,6,6-trimethyl-5-oxobicyclo[2.2.2]octane-2-carboxylic acid methyl ester
- 5986-55-0
patchoulol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1.1: 93 percent / MeONa / methanol; H2O / 8 h / Heating 2.1: oxalyl chloride / benzene / 2 h / 20 °C 3.1: DMAP / benzene / 1 h / Heating 4.1: 20 mg / AIBN; tributyltin hydride / benzene / 5 h / Heating 5.1: ozone; NaHCO3 / methanol; CH2Cl2 5.2: 93 percent / dimethyl sulfide / methanol; CH2Cl2 / 10 h / 20 °C 6.1: 82 percent / tetrahydrofuran / 1 h / 0 °C 7.1: 68 percent / DMAP; DIPEA / dimethylformamide / 16 h / 20 °C 8.1: 19 percent / sodium / tetrahydrofuran / 16 h / Heating 9.1: 99 percent / hydrogen / palladium on activated charcoal / 12 h / 20 °C View Scheme |
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Chemistry
Molecular Structure:
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Molecular Formula: C15H26O
Molecular Weight: 222.37
Systematic Name: (1R,4S,4aS,6R,8aS)-4,8a,9,9-Tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol
Synonyms of Patchouli alcohol (CAS NO.5986-55-0): EINECS 227-807-2 ; (1R-(1alpha,4beta,4aalpha,6beta,8aalpha))-Octahydro-4,8a,9,9-tetramethyl-1,6-methano-1(2H)-naphthol ; 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1R,4S,4aS,6R,8aS)-
CAS NO: 5986-55-0
Product Categories: Organics
Index of Refraction: 1.515
Molar Refractivity: 66.964 cm3
Molar Volume: 222.087 cm3
Surface Tension: 38.309 dyne/cm
Density: 1.001 g/cm3
Flash Point: 120.179 °C
Enthalpy of Vaporization: 61.111 kJ/mol
Boiling Point of Patchouli alcohol (CAS NO.5986-55-0): 287.443 °C at 760 mmHg
Uses
Patchouli alcohol (CAS NO.5986-55-0) is used in the synthesis of the chemotherapy drug Taxol.