Patchouli alcohol supplier | CasNO.5986-55-0

Name
Patchouli alcohol
EINECS 227-807-2
CAS No. 5986-55-0
Article Data5
CAS DataBase
Density 1.001 g/cm³
Solubility 41.8mg/L at 24℃
Melting Point 56°; mp (racemate) 39-40° (Danishevsky, Dumas); mp 46-47° (Mirrington, Schmalzl)
Formula C₁₅H₂₆O
Boiling Point 287.443 °C at 760 mmHg
Molecular Weight 222.371
Flash Point 120.179 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 20.23000
LogP 3.60980

Synthetic route

: (+)-(1S,3R,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undec-5-en-3-ol

: 5986-55-0
patchoulol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal at 20℃; for 12h;	99%

: 4a-Hydroxy-8-oxo-2,5,5,8a-tetramethyl-1,6-methano-decahydro-naphthalin

: 5986-55-0
patchoulol

Conditions

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

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

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

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

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

: (1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carbonyl chloride

: 5986-55-0
patchoulol

Conditions

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

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

: (1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester

: 5986-55-0
patchoulol

Conditions

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

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

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

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

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

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

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

: 912289-98-6
difluorosulfoacetic acid sodium salt

: 5986-55-0
patchoulol

: C17H25F2O5S(1-)*Na(1+)

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Reflux;	91.4%
With toluene-4-sulfonic acid In toluene for 18h; Reflux;	71.8%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1119360-53-0
1,1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt

: 5986-55-0
patchoulol

: C18H27F2O6S(1-)*Na(1+)

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; patchoulol In pyridine; dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: 1,1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt In pyridine; dichloromethane for 10h;	90%
Stage #1: bis(trichloromethyl) carbonate; patchoulol With pyridine In dichloromethane at 0 - 25℃; for 3h; Inert atmosphere; Stage #2: 1,1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt In dichloromethane for 10h; Inert atmosphere;	72%

...Expand

: 35657-98-8
ethyl 2-bromo-2-cyclopentylacetate

: 5986-55-0
patchoulol

: C24H40O3

Conditions

Conditions	Yield
Stage #1: patchoulol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl 2-bromo-2-cyclopentylacetate at 25℃; for 6.33333h;	89%
Stage #1: patchoulol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl 2-bromo-2-cyclopentylacetate In tetrahydrofuran at 25℃; for 6.33333h; Inert atmosphere;	80.3%

: 105-36-2
ethyl bromoacetate

: 5986-55-0
patchoulol

: C19H32O3

Conditions

Conditions	Yield
Stage #1: patchoulol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl bromoacetate at 25℃; for 6.33333h;	83%

: sodium carboxymethyl sulfonate

: 5986-55-0
patchoulol

: C17H27O5S(1-)*Na(1+)

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Reflux;	76.5%

: 463-51-4
Ketene

: 5986-55-0
patchoulol

: 67152-05-0
(1S)-4a-acetoxy-2c,5,5,8a-tetramethyl-(4at,8at)-decahydro-1r,6-methano-naphthalene

Conditions

Conditions	Yield
With diethyl ether; sulfuric acid

: 64-18-6
formic acid

: 5986-55-0
patchoulol

: 514-51-2, 92841-73-1
β-patchoulene

Conditions

Conditions	Yield
Erwaermen auf dem Dampfbad;

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

: 5986-55-0
patchoulol

: 514-51-2, 92841-73-1
β-patchoulene

...Expand

: 5986-55-0
patchoulol

: 514-51-2, 92841-73-1
(1S,4R,7R)-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene

Conditions

Conditions	Yield
With iodine
With sulfuric acid

: 5986-55-0
patchoulol

: 70473-08-4
4β-10α-Dimethyl-11-hydroxy-eudesman-1-on

Conditions

Conditions	Yield
With lead(IV) acetate; calcium carbonate In benzene

: 5986-55-0
patchoulol

: 560-32-7
(1α,3aα,7α,8aβ)-2,3,6,7,8,8a-hexahydro-1,4,9,9-tetramethyl-1H-3a,7-methanoazulene

Conditions

Conditions	Yield
With trichlorophosphate

: 5986-55-0
patchoulol

: 2,2,6,8-Tetramethyl-bicyclo<5.3.1>undec-7-en-3-on

Conditions

Conditions	Yield
With lead(IV) acetate; calcium carbonate In benzene

: 103-71-9
phenyl isocyanate

: 5986-55-0
patchoulol

: 118723-81-2
Phenyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester

Conditions

Conditions	Yield
With n-butyllithium 1.) n-heptane, n-hexane, 30 min, 2.) 30 min; Yield given. Multistep reaction;

: 5986-55-0
patchoulol

: 1795-48-8
Isopropyl isocyanate

: 118864-79-2
Isopropyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester

Conditions

Conditions	Yield
With n-butyllithium 1.) n-heptane, n-hexane, 30 min, 2.) 30 min; Yield given. Multistep reaction;

: 5986-55-0
patchoulol

: 1609-86-5
Tert-butyl isocyanate

: 118864-80-5
tert-Butyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester

Conditions

Conditions	Yield
With n-butyllithium 1.) n-heptane, 30 min, 2.) 30min, n.heptane; Yield given. Multistep reaction;

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 9α-hydroxypatchoulol

Conditions

Conditions	Yield
With Mucor plumbeus In ethanol for 120h; Oxidation; microbiological hydroxylation;	A 100 mg B 178 mg

: 5986-55-0
patchoulol

palladium/charcoal: palladium/charcoal

: 489-84-9
7-isopropyl-1,4-dimethyl-azulene

: 5986-55-0
patchoulol

selenium: selenium

: 489-84-9
7-isopropyl-1,4-dimethyl-azulene

: 60-29-7
diethyl ether

: 7664-93-9
sulfuric acid

: 5986-55-0
patchoulol

: 514-51-2, 92841-73-1
β-patchoulene

...Expand

: 7553-56-2
iodine

: 5986-55-0
patchoulol

: 514-51-2, 92841-73-1
β-patchoulene

: 5986-55-0
patchoulol

H3BO3: H3BO3

: 514-51-2, 92841-73-1
β-patchoulene

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 9α-hydroxypatchoulol

C: 221694-02-6
(-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one

D: (7S)-7-hydroxypatchoulol

Conditions

Conditions	Yield
With sodium nitrate; potassium dihydrogenphosphate; D-glucose; Botrytis cinerea; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate; yeast extract In ethanol; water at 25℃; for 72h; Further byproducts given;	A 11 mg B 4.3 mg C 28 mg D 47 mg

...Expand

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 221694-02-6
(-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one

C: (3R)-3-hydroxypatchoulol

D: (7S)-7-hydroxypatchoulol

Conditions

Conditions	Yield
With sodium nitrate; potassium dihydrogenphosphate; D-glucose; Botrytis cinerea; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate; yeast extract In ethanol; water at 25℃; for 72h; Further byproducts given;	A 11 mg B 28 mg C 1 mg D 47 mg

...Expand

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 221694-02-6
(-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one

C: (7S)-7-hydroxypatchoulol

D: (8S)-8-hydroxypatchoulol

Conditions

Conditions	Yield
With sodium nitrate; potassium dihydrogenphosphate; D-glucose; Botrytis cinerea; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate; yeast extract In ethanol; water at 25℃; for 72h; Further byproducts given;	A 11 mg B 28 mg C 47 mg D 3.6 mg

...Expand

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 221694-02-6
(-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one

C: (7S)-7-hydroxypatchoulol

D: 13-hydroxypatchoulol

Conditions

Conditions	Yield
With sodium nitrate; potassium dihydrogenphosphate; D-glucose; Botrytis cinerea; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate; yeast extract In ethanol; water at 25℃; for 72h; Further byproducts given;	A 11 mg B 28 mg C 47 mg D 1 mg

...Expand

: 5986-55-0
patchoulol

A: 66865-18-7
5α-hydroxypatchoulol

B: 221694-02-6
(-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one

C: (7S)-7-hydroxypatchoulol

D: (2S)-2,14-dihydroxypatchoulol

Conditions

Conditions	Yield
With sodium nitrate; potassium dihydrogenphosphate; D-glucose; Botrytis cinerea; magnesium sulfate; iron(II) sulfate; zinc(II) sulfate; yeast extract In ethanol; water at 25℃; for 72h; Further byproducts given;	A 11 mg B 28 mg C 47 mg D 1.5 mg

...Expand

Patchouli alcohol Chemical Properties

Molecular Structure:

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

Patchouli alcohol Uses

Patchouli alcohol (CAS NO.5986-55-0) is used in the synthesis of the chemotherapy drug Taxol.

Product Name

Patchouli alcohol

Synthetic route

Patchouli alcohol Chemical Properties

Patchouli alcohol Uses

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