Patchouli alcohol

Base Information

• Chemical Name: Patchouli alcohol
• CAS No.: 5986-55-0
• Deprecated CAS: 1366-08-1
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 29061990
• European Community (EC) Number: 227-807-2
• UNII: HHH8CPR1M2
• DSSTox Substance ID: DTXSID9052266
• Wikipedia: Patchoulol
• Wikidata: Q7144372
• Metabolomics Workbench ID: 53348
• ChEMBL ID: CHEMBL4588682
• Mol file: 5986-55-0.mol

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;

Chemical Property of Patchouli alcohol

Chemical Property:

• Vapor Pressure: 0.000278mmHg at 25°C
• Melting Point: 56°; mp (racemate) 39-40° (Danishevsky, Dumas); mp 46-47° (Mirrington, Schmalzl)
• Refractive Index: 1.514
• Boiling Point: 287.443 °C at 760 mmHg
• PKA: 15.23±0.70(Predicted)
• Flash Point: 120.179 °C
• PSA: 20.23000
• Density: 1.001 g/cm³
• LogP: 3.60980
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: 41.8mg/L at 24℃
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 321

Purity/Quality:

99.9% ^*data from raw suppliers

Patchouli Alcohol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3CCC2(C1C3)C)(C)C)O
• Isomeric SMILES: C[C@H]1CC[C@@]2([C@@]3([C@H]1C[C@H](C2(C)C)CC3)C)O
• Description: Herbal oils are of various types depending on herbs used to extract the oil. The most important bioactive constituents of plants are alkaloids, tannins, flavonoids, and phenolic compounds. Amongst popular oils, Patchouli oil extracted from Pogostemon cablin is known not just for its health benefits but also for its fragrance. Patchouli is a perennial herb and a fragrant plant that basically grows in the tropical region throughout the world. Though patchouli oil is known for its perfumery uses and there are other medicinal properties attached with patchouli oil. Patchouli oil’s growing demand can be understood as it can neither be replaced inorganically nor synthesized because of its complex molecular structure. Hence, the only alternative is to cultivate the plant extensively. The aim of the present paper is to review the importance of patchouli extractions in the treatment of diseases that may be useful for the applications of this medicinal plant in the treatment of diseases.
• Uses: Patchouli alcohol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps, non-cosmetic products such as household cleaners and detergents. Patchoulic alcohol is commonly used as an indicator for the quality assessment of dried P. cablin. It also used as daily dosage along with other herbs for treatment of asthma. Patchouli Alcohol is a sesquiterpene extract which has been tested against insects and fungus, it is an antibacterial or insecticidal agent.

Technology Process of Patchouli alcohol

There total 22 articles about Patchouli alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

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

Guidance literature:

With hydrogen; palladium on activated charcoal; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2005.11.012

Reference yield: 83.0%

(4aR,6S,8aR)-4,8a,9,9-Tetramethyl-4a,5,6,7,8,8a-hexahydro-2H-1,6-methano-naphthalen-1-ol (17806-54-1,77584-13-5) → (+/-) patchoulol (5986-55-0,21682-90-6,21682-91-7,26263-41-2,59905-13-4,79897-91-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; for 12h;

DOI:10.1016/S0040-4039(00)71484-5

Reference yield:

4a-Hydroxy-8-oxo-2,5,5,8a-tetramethyl-1,6-methano-decahydro-naphthalin → patchoulol (5986-55-0)

Guidance literature:

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

DOI:10.1021/ja01074a041

upstream raw materials:

(4aR,6S,8aR)-4,8a,9,9-Tetramethyl-4a,5,6,7,8,8a-hexahydro-2H-1,6-methano-naphthalen-1-ol

2,6,6-trimethyl-2-cyclohexene-1,4-dione

2,6,6-trimethylcyclohexa-2,4-dienone

(1SR,4SR,7SR)-1,3,3-trimethyl-7-acetylbicyclo[2.2.2]oct-5-en-2-one

Downstream raw materials:

β-patchoulene

7-isopropyl-1,4-dimethyl-azulene

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

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

Refernces

• 1、 Bertrand, M.,Teisseire, P.,Pelerin, G.. "SUR UNE SOLUTION DE RECHANGE A LA CYCLISATION DES ε-HALOGENOCETONES - APPLICATION A LA SYNTHESE DU (+/-) PATCHOULOL.". . p. 2055 - 2056. Retrieved 2007/10/02.