5986-55-0

Usage

Uses

Used in Cosmetics and Personal Care Industry:
Patchouli alcohol is used as a fragrance ingredient in decorative cosmetics, fine fragrances, shampoos, and toilet soaps. Its unique scent and medicinal properties make it a popular choice for enhancing the sensory experience and providing potential therapeutic benefits.
Used in Household Products Industry:
Patchouli alcohol is used as a fragrance ingredient in non-cosmetic products such as household cleaners and detergents. Its addition to these products can improve the overall sensory experience and provide potential health benefits.
Used in Herbal Medicine:
Patchouli alcohol is used as an indicator for the quality assessment of dried P. cablin and is commonly used as a daily dosage along with other herbs for the treatment of asthma. Its medicinal properties make it a valuable component in traditional herbal remedies.
Used in Agriculture:
Patchouli alcohol is a sesquiterpene extract that has been tested against insects and fungi. It is used as an antibacterial or insecticidal agent, providing a natural and effective method for pest control in agriculture.
Used in Aromatherapy:
Due to its fragrant properties, Patchouli alcohol is used in aromatherapy for its potential mood-enhancing and stress-relieving effects. Its unique scent can help create a calming and relaxing atmosphere, promoting mental well-being.

Flammability and Explosibility

Notclassified

Synthetic route

(+)-(1S,3R,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undec-5-en-3-ol → patchoulol (5986-55-0)

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 → patchoulol (5986-55-0)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 175 - 220℃;

(1S,4R,6R)-6-(2-hydroxybut-3-en-2-yl)-1,3,3-trimethylbicyclo[2.2.2]octan-2-one (874747-37-2) → patchoulol (5986-55-0)

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

(1S,4R,6R)-6-[2-(methoxymethyloxy)but-3-en-2-yl]-1,3,3-trimethylbicyclo[2.2.2]octan-2-one (874747-39-4) → patchoulol (5986-55-0)

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

(1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid (874747-38-3) → patchoulol (5986-55-0)

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

(1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carbonyl chloride → patchoulol (5986-55-0)

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

(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 → patchoulol (5986-55-0)

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

(-)-(1S,4R,6S)-6-isopropenyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one (132060-03-8) → patchoulol (5986-55-0)

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

(-)-(1S,4R,6R)-6-acetyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one (132152-67-1) → patchoulol (5986-55-0)

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

(-)-(1S,2R,4S,8S)-8-isopropenyl-4,6,6-trimethyl-5-oxobicyclo[2.2.2]octane-2-carboxylic acid methyl ester (733001-15-5) → patchoulol (5986-55-0)

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

difluorosulfoacetic acid sodium salt (912289-98-6) + patchoulol (5986-55-0) → C17H25F2O5S(1-)*Na(1+)

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%

bis(trichloromethyl) carbonate (32315-10-9) + 1,1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (1119360-53-0) + patchoulol (5986-55-0) → C18H27F2O6S(1-)*Na(1+)

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%

ethyl 2-bromo-2-cyclopentylacetate (35657-98-8) + patchoulol (5986-55-0) → C24H40O3

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%

ethyl bromoacetate (105-36-2) + patchoulol (5986-55-0) → C19H32O3

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 + patchoulol (5986-55-0) → C17H27O5S(1-)*Na(1+)

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

Ketene (463-51-4) + patchoulol (5986-55-0) → (1S)-4a-acetoxy-2c,5,5,8a-tetramethyl-(4at,8at)-decahydro-1r,6-methano-naphthalene (67152-05-0)

Conditions	Yield
With diethyl ether; sulfuric acid

formic acid (64-18-6) + patchoulol (5986-55-0) → β-patchoulene (514-51-2, 92841-73-1)

Conditions	Yield
Erwaermen auf dem Dampfbad;

sodium acetate (127-09-3) + acetic anhydride (108-24-7) + patchoulol (5986-55-0) → β-patchoulene (514-51-2, 92841-73-1)

patchoulol (5986-55-0) → (1S,4R,7R)-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene (514-51-2, 92841-73-1)

Conditions	Yield
With iodine
With sulfuric acid

patchoulol (5986-55-0) → 4β-10α-Dimethyl-11-hydroxy-eudesman-1-on (70473-08-4)

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

patchoulol (5986-55-0) → (1α,3aα,7α,8aβ)-2,3,6,7,8,8a-hexahydro-1,4,9,9-tetramethyl-1H-3a,7-methanoazulene (560-32-7)

Conditions	Yield
With trichlorophosphate

patchoulol (5986-55-0) → 2,2,6,8-Tetramethyl-bicyclo<5.3.1>undec-7-en-3-on

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

phenyl isocyanate (103-71-9) + patchoulol (5986-55-0) → Phenyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester (118723-81-2)

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

patchoulol (5986-55-0) + Isopropyl isocyanate (1795-48-8) → Isopropyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester (118864-79-2)

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

patchoulol (5986-55-0) + Tert-butyl isocyanate (1609-86-5) → tert-Butyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester (118864-80-5)

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

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + 9α-hydroxypatchoulol

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

patchoulol (5986-55-0) + palladium/charcoal → 7-isopropyl-1,4-dimethyl-azulene (489-84-9)

patchoulol (5986-55-0) + selenium → 7-isopropyl-1,4-dimethyl-azulene (489-84-9)

diethyl ether (60-29-7) + sulfuric acid (7664-93-9) + patchoulol (5986-55-0) → β-patchoulene (514-51-2, 92841-73-1)

iodine (7553-56-2) + patchoulol (5986-55-0) → β-patchoulene (514-51-2, 92841-73-1)

patchoulol (5986-55-0) + H3BO3 → β-patchoulene (514-51-2, 92841-73-1)

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + 9α-hydroxypatchoulol + (-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one (221694-02-6) + (7S)-7-hydroxypatchoulol

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

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + (-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one (221694-02-6) + (3R)-3-hydroxypatchoulol + (7S)-7-hydroxypatchoulol

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

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + (-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one (221694-02-6) + (7S)-7-hydroxypatchoulol + (8S)-8-hydroxypatchoulol

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

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + (-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one (221694-02-6) + (7S)-7-hydroxypatchoulol + 13-hydroxypatchoulol

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

patchoulol (5986-55-0) → 5α-hydroxypatchoulol (66865-18-7) + (-)-(1R,3R,6S,7S,8S,10R)-3-hydroxy-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-10-one (221694-02-6) + (7S)-7-hydroxypatchoulol + (2S)-2,14-dihydroxypatchoulol

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

Upstream product

• 733001-15-5 (-)-(1S,2R,4S,8S)-8-isopropenyl-4,6,6-trimethyl-5-oxobicyclo[2.2.2]octane-2-carboxylic acid methyl ester 
• 874747-37-2 (1S,4R,6R)-6-(2-hydroxybut-3-en-2-yl)-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 77584-09-9 (1R,4S,6S)-6-((S)-1-Methoxymethoxy-1-methyl-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 21682-95-1 6-endo-acetyl-1,3,3-trimethylbicyclo<2.2.2>octan-2-one 
• 21682-95-1 (1R,4S,6R)-6-Acetyl-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 17806-54-1 (4aR,6S,8aR)-4,8a,9,9-Tetramethyl-4a,5,6,7,8,8a-hexahydro-2H-1,6-methano-naphthalen-1-ol 
• 132152-67-1 (-)-(1S,4R,6R)-6-acetyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 132060-03-8 (-)-(1S,4R,6S)-6-isopropenyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 874747-38-3 (1S,2R,4S,8S)-8-Isopropenyl-4,6,6-trimethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid 
• 874747-39-4 (1S,4R,6R)-6-[2-(methoxymethyloxy)but-3-en-2-yl]-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 77584-12-4 (1R,4S,6S)-6-((S)-1-Hydroxy-1-methyl-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 21682-92-8 (1SR,4SR,7SR)-1,3,3-trimethyl-7-acetylbicyclo[2.2.2]oct-5-en-2-one 
• 13487-30-4 2,6,6-trimethylcyclohexa-2,4-dienone 

Downstream Products

• 514-51-2 β-patchoulene 
• 489-84-9 7-isopropyl-1,4-dimethyl-azulene 
• 118723-81-2 Phenyl-carbamic acid (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyl-octahydro-1,6-methano-naphthalen-1-yl ester 
• 560-32-7 (1α,3aα,7α,8aβ)-2,3,6,7,8,8a-hexahydro-1,4,9,9-tetramethyl-1H-3a,7-methanoazulene 
• 514-51-2 (1S,4R,7R)-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene 

Relevant academic research and scientific papers

An enantiospecific total synthesis of (-)-patchouli alcohol

An enantiospecific total synthesis of patchouli alcohol, starting from the readily available monoterpene (R)-carvone, has been accomplished. A tandem double Michael reaction-alkylation sequence and single electron mediated 6-endo trig cyclisation reaction have been employed as key steps.

SUR UNE SOLUTION DE RECHANGE A LA CYCLISATION DES ε-HALOGENOCETONES - APPLICATION A LA SYNTHESE DU (+/-) PATCHOULOL.

A short synthesis of (+/-) patchoulol is described in wich the cyclisation of the methoxymethylether from a δ-ethylenic γ-hydroxyketone constitutes the key step.