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patchouli alcohol

Chemical Structure

General Material Information

Preferred name patchouli alcohol
Trivial Name Patchouli alcohol
Short Description 1,6-methanonaphthalen-1(2H)-ol, octahydro-4,8a,9
Formula C15 H26 O
CAS Number 5986-55-0
Deleted CAS Number 1366-08-1
ECHA Number 227-807-2
FDA UNII HHH8CPR1M2
Beilstein Number 2553847
MDL MFCD00209526
xLogP3-AA 4.10 (est)
NMR Predictor External link
Synonyms
  • 1,6-methanonaphthalen-1(2H)-ol, octahydro-4,8a,9
  • (1R-(1alpha,4beta, 4aalpha,6beta,8aalpha))- octahydro-4,8a,9,9-tetramethyl-1,6-methano-1(2H)-naphthol
  • octahydrotetramethyl methano-1-naphthol
  • patchouli camphor
  • patchoulol
  • (-)- patchoulol
  • 2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
  • 2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
  • 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1R,4S,4aS,6R,8aS)-
  • 1,6-Methanonaphthalen-1β(2H)-ol, 3,4,4aβ,5,6β,7,8,8a-octahydro-4α,8aβ,9,9-tetramethyl-
  • 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, [1R-(1α,4β,4aα,6β,8aα)]-
  • (1R,4S,4aS,6R,8aS)-Octahydro-4,8a,9,9-tetramethyl-1,6-methanonaphthalen-1(2H)-ol
  • (-)-Patchoulol
  • (-)-Patchouli alcohol
  • (1R,4S,4AS,6R,8aS)-4,8a,9,9-tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol

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Literature & References

Leffingwell:Chirality or Article
2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:5986-55-0
Pubchem (cid):521903
Pubchem (sid):3881601
Publications by PubMed
Prevention of UV radiation-induced cutaneous photoaging in mice by topical administration of patchouli oil.
Expression, purification and activity assay of a patchoulol synthase cDNA variant fused to thioredoxin in Escherichia coli.
Characterization of solid dispersions of Patchouli alcohol with different polymers: effects on the inhibition of reprecipitation and the improvement of dissolution rate.
[Study on constituents of the aerial parts of Pogostemon cablin].
Evaluation of the antibacterial activity of patchouli oil.
Identification of repellent and insecticidal constituents of the essential oil of Artemisia rupestris L. aerial parts against Liposcelis bostrychophila Badonnel.
Immunologic mechanism of Patchouli alcohol anti-H1N1 influenza virus may through regulation of the RLH signal pathway in vitro.
Antifungal effect of Allium tuberosum, Cinnamomum cassia, and Pogostemon cablin essential oils and their components against population of Aspergillus species.
Insecticidal and repellence activity of the essential oil of Pogostemon cablin against urban ants species.
Patchouli alcohol, an essential oil of Pogostemon cablin, exhibits anti-tumorigenic activity in human colorectal cancer cells.
Virtual screening of compounds from the patchouli oil of Pogostemon herba for COX-1 inhibition.
Anti-inflammatory activity of patchouli alcohol in RAW264.7 and HT-29 cells.
[Quantitative model for patchouli alcohol in Pogostemon cablin by near-infrared spectroscopy].
Quantitative and physical evaluation of patchouli essential oils obtained from different sources of Pogostemon cablin.
Technology for efficient and successful delivery of vermicompost colonized bioinoculants in Pogostemon cablin (patchouli) Benth.
Enhancing the copy number of episomal plasmids in Saccharomyces cerevisiae for improved protein production.
Selective separation of patchouli alcohol from the essential oil of Cablin potchouli by inclusion crystalline method.
Acaricidal activity of DHEMH, derived from patchouli oil, against house dust mite, Dermatophagoides farinae.
Oral administration of patchouli alcohol isolated from Pogostemonis Herba augments protection against influenza viral infection in mice.
Chemical constituents, antioxidant and antimocrobial activity of essential oil of Pogostemon paniculatus (Willd.).
Chemical diversity in the essential oil of Indian valerian (Valeriana jatamansi Jones).
Enhanced extraction of patchouli alcohol from Pogostemon cablin by microwave radiation-accelerated ionic liquid pretreatment.
Anti-inflammatory activity of patchouli alcohol isolated from Pogostemonis Herba in animal models.
Inhibitory effect and possible mechanism of action of patchouli alcohol against influenza A (H2N2) virus.
Involvement of nitric oxide (NO) signalling pathway in the antidepressant activity of essential oil of Valeriana wallichii Patchouli alcohol chemotype.
Patchouli alcohol: in vitro direct anti-influenza virus sesquiterpene in Pogostemon cablin Benth.
Anti-inflammatory effect of patchouli alcohol isolated from Pogostemonis Herba in LPS-stimulated RAW264.7 macrophages.
Terpenoid compositions and antioxidant activities of two Indian valerian oils from the Khasi Hills of north-east India.
Antidepressant effect of Valeriana wallichii patchouli alcohol chemotype in mice: Behavioural and biochemical evidence.
Volatile oil composition of Pogostemon heyneanus and comparison of its composition with patchouli oil.
Sedative effects of vapor inhalation of the essential oil of Microtoena patchoulii and its related compounds.
Diversion of flux toward sesquiterpene production in Saccharomyces cerevisiae by fusion of host and heterologous enzymes.
[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].
[Identification method with significant specificity of volatile oil of Pogostemon cablin].
Elucidation of possible mechanism of analgesic action of Valeriana wallichii DC chemotype (patchouli alcohol) in experimental animal models.
Chemical analysis and biological activity of the essential oils of two valerianaceous species from China: Nardostachys chinensis and Valeriana officinalis.
Qualitative analysis of the smoke-stream of different kinds of incense by SPME/GC-MS.
Novel silicon-based patchouli odorants of the trialkyl(1-hydroxy-1-methylethyl)silane type: design, synthesis, and olfactory properties.
[Self-microemulsifying drug delivery system of patchoulic alcohol to improve oral bioavailability in rats].
[Studies on characteristics of volatile oil and micro-identification between Herba Pogostemonis and Herba Agastachis rugosae].
Doubly deuterium-labeled patchouli alcohol from cyclization of singly labeled [2-(2)H(1)]farnesyl diphosphate catalyzed by recombinant patchoulol synthase.
Kanokonyl acetate-rich Indian valerian from northwestern Himalaya.
Chemical composition, oviposition deterrent and larvicidal activities against Aedes aegypti of essential oils from Piper marginatum Jacq. (Piperaceae).
Convenient TLC-based Identification Test for the Crude Drug "Pogostemoni Herba".
Insecticidal activity of Valeriana jatamansi (Valerianaceae) against mosquitoes.
Fragrance material review on patchouli alcohol.
Woody pretzels: spirocycles from vetiver to patchouli and Georgywood.
Comparative study on volatile components of Nardostachys rhizome.
Production of plant sesquiterpenes in Saccharomyces cerevisiae: effect of ERG9 repression on sesquiterpene biosynthesis.
Antioxidant activities and volatile constituents of various essential oils.
Solubility of the sesquiterpene alcohol patchoulol in supercritical carbon dioxide.
Compositional diversity of terpenoids in the Himalayan Valeriana genera.
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
Engineering the essence of plants.
Redirection of cytosolic or plastidic isoprenoid precursors elevates terpene production in plants.
The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases.
GC-MS fingerprint of Pogostemon cablin in China.
Determination of patchoulic alcohol in Herba Pogostemonis by GC-MS-MS.
[Re-study on characteristic fingerprint of volatile oil from Herba Pogostemonis by GC].
[Investigation on the influential factors of the volatile oil and main constituent content in Pogostemon cablin].
[Study on purification technology of patchouly oil with molecular distillation].
[Pharmacokinetics of patchouli alcohol and patchouli alcohol in patchouli oil after iv administrated to rats].
New sesquiterpene hydroperoxides with trypanocidal activity from Pogostemon cablin.
The effect of essential oils on methicillin-resistant Staphylococcus aureus using a dressing model.
Toxicity and repellency of patchouli oil and patchouli alcohol against Formosan subterranean termites Coptotermes formosanus Shiraki (Isoptera: Rhinotermitidae).
[Constituents analysis on volatile oil of Pogostemon cablin from different collection time cultivated in Hainan].
[GC-MS analysis of volatile oil of Herba Pogostemonis collected from Leizhou county].
[GC-MS analysis of volatile oil of herba Pogostemonis collected from Gaoyao county].
[Study on the chemical constituents of the volatile oil from Lysimachia trientaloides Hemsl].
Anti-emetic principles of Pogostemon cablin (Blanco) Benth.
Biotransformation of the fungistatic sesquiterpenoid patchoulol by botrytis cinerea
[Chemical constituents of Pogostemon cablin (Blanco) Benth].
Purification and characterization of the sesquiterpene cyclase patchoulol synthase from Pogostemon cablin.
The screening of Chinese crude drugs for Ca2+ antagonist activity: identification of active principles from the aerial part of Pogostemon cablin and the fruits of Prunus mume.
Biosynthesis of the sesquiterpene patchoulol from farnesyl pyrophosphate in leaf extracts of Pogostemon cablin (patchouli): mechanistic considerations.
Regio-selective 10-hydroxylation of patchoulol, a sesquiterpene, by pithomyces species.
[Patchouli alcohol and beta patchoulene from Nardostachys chinensis].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C09705
HMDB (The Human Metabolome Database):Search
FooDB:FDB007819
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Melting Point 55 to 58°C @ 760 mm Hg
Boiling Point 287 to 288°C @ 760 mm Hg
Vapor Pressure 0.000278 mmHg @ 25 °C
Flash Point TCC Value 101.67 °C TCC
logP (o/w) 4.484 est
Solubility
alcohol Yes
water, 42.87 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Woody
patchouli, earthy, camphoreous, powdery
Odor strength low
General comment At 100.00 %. patchouli earthy camphor powdery

Occurrences

Potential Uses

Applications
Odor purposes Amber, Balsam, Floral, Herbal, Moss, Patchouli, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
maximum skin levels for fine fragrances:
0.0200 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2004)
Recommendation for patchouli alcohol usage levels up to:
40.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.1100 %
Dermal Systemic Exposure in Cosmetic Products:
0.0028 mg/kg/day (IFRA, 2004)
Recommendation for patchouli alcohol flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):5986-55-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :521903
National Institute of Allergy and Infectious Diseases:Data
2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
Chemidplus:0005986550