Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H26O |
Molecular Weight | 222.3663 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1CC[C@@]2(O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@H]1C3
InChI
InChIKey=GGHMUJBZYLPWFD-CUZKYEQNSA-N
InChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28421121Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28095424 | https://www.ncbi.nlm.nih.gov/pubmed/22977538
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28421121
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28095424 | https://www.ncbi.nlm.nih.gov/pubmed/22977538
Patchouli alcohol is a sesquiterpene with tricyclic structure and has been extracted from the whole plant of traditional Chinese medicine Guang-huo-xiang, which is also called Pogostemon cablin(Blanco) Benth. Patchouli alcohol is the nominal ingredient which standing for the typical aromatic odor and also used as the chemical reference for the quality control of P. cablin in Chinese Pharmacopoeia. Patchouli alcohol has exhibited various pharmacological activities, such as protecting against the neurotoxicity of beta-amyloid peptide fragment 25–35 (Aβ25–35), enhancing cognition in memory impairment mice induced by scopolamine, anti-inflammatory activities in RAW 264.7 cells and rats models, anti-influenza virus activities in vitro and in vivo. However, Patchouli alcohol easily evaporates even at room temperature due to its volatile nature, which can cause the bioactivity decrease in the processing and storage. In addition, the development of Patchouli alcohol as medicine is greatly limited due to its low water solubility and poor bioavailability. Patchoulol is also used in the synthesis of the chemotherapy drug Taxol.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28421121 |
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Target ID: WP1018 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28421121 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28421121
Oral administration of PA (10, 20, and 40mg/Kg) could remarkably relieve xyleneinduced ear edema in mice as well as carrageenan-induced paw edema in rats
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22977538
The RAW264.7 cell line were maintained in RPMI-1640 medium supplemented with 2 mM glutamine, antibiotics (100 U/ml penicillin and 100 U/ml streptomycin) and 10% heat-inactivated FBS at 37˚C in a humidified atmosphere of 95% air and 5% CO2. The cells were seeded onto 96-well culture plates at 5x104 cells/well, unless otherwise specified. After seeding for 24 h, the cells were cultured in serum-free medium and incubated with different concentrations of PA (Patchouli alcohol ) (final concentrations: 0, 10, 20 and 40 µM) for 2 h. LPS at a final concentration of 100 ng/ml was then added for an additional 24 h. In vitro test, the increased productions of TNF-𝛼, IL-1𝛽, IL-6, PGE2, and NO and mRNA expressions of TNF-𝛼, IL-1𝛽, IL-6, iNOS, and Cox-2 in RAW264.7 cells (a mouse macrophages cell line) stimulated by lipopolysaccharide (LPS) which was endotoxin from Germnegative bacteria were reversed after pretreatment with PA (Patchouli alcohol ) at the concentrations of 10 𝜇M, 20 𝜇M, or 40 𝜇M
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5986-55-0
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227-807-2
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7940
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10955174
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PATCHOULOL
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HHH8CPR1M2
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DTXSID9052266
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m8427
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PRIMARY | Merck Index |
SUBSTANCE RECORD