5986-55-0

Basic information

• Product Name: Patchouli alcohol
• Synonyms: (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)-; (4S,8aS)-4,8a,9,9-tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol; 4,8a,9,9-tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol; (1R,4S,4aR,6R,8aS)-4,8a,9,9-tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol
• CAS NO: 5986-55-0
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.3663
• EINECS: 227-807-2
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Organics
• Mol File: 5986-55-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 56°; mp (racemate) 39-40° (Danishevsky, Dumas); mp 46-47° (Mirrington, Schmalzl)
• Boiling Point: 287.4°C at 760 mmHg
• Flash Point: 120.2°C
• Density: 1.001g/cm³
• Vapor Pressure: 0.000278mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 15.23±0.70(Predicted)
• Water Solubility: 41.8mg/L at 24℃
• CAS DataBase Reference: Patchouli alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Patchouli alcohol(5986-55-0)
• EPA Substance Registry System: Patchouli alcohol(5986-55-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 5986-55-0(Hazardous Substances Data)

Usage

Description

Patchouli alcohol, also known as Patchoulol, is a carbotricyclic compound and sesquiterpenoid tertiary alcohol derived from the fragrant plant Pogostemon cablin. It is a tricyclo[5.3.1.03,8]undecan-3-ol with methyl groups substituted at positions 2, 2, 6, and 8, and has the 1R,3R,6S,7S,8S-diastereoisomer configuration. Patchouli alcohol is valued not only for its distinctive fragrance but also for its medicinal properties and complex molecular structure, which cannot be synthesized or replaced inorganically.

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

• 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 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 13487-30-4 2,6,6-trimethylcyclohexa-2,4-dienone 
• 21682-92-8 (1SR,4SR,7SR)-1,3,3-trimethyl-7-acetylbicyclo[2.2.2]oct-5-en-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 
• 21682-95-1 (1R,4S,6R)-6-Acetyl-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 
• 77584-09-9 (1R,4S,6S)-6-((S)-1-Methoxymethoxy-1-methyl-allyl)-1,3,3-trimethyl-bicyclo[2.2.2]octan-2-one 
• 874747-37-2 (1S,4R,6R)-6-(2-hydroxybut-3-en-2-yl)-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 874747-39-4 (1S,4R,6R)-6-[2-(methoxymethyloxy)but-3-en-2-yl]-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 
• 132060-03-8 (-)-(1S,4R,6S)-6-isopropenyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 132152-67-1 (-)-(1S,4R,6R)-6-acetyl-1,3,3-trimethylbicyclo[2.2.2]octan-2-one 
• 733001-15-5 (-)-(1S,2R,4S,8S)-8-isopropenyl-4,6,6-trimethyl-5-oxobicyclo[2.2.2]octane-2-carboxylic acid methyl ester 

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 articles and documents

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.