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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
Structure of PATCHOULI ALCOHOL

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

HIDE SMILES / InChI

Molecular Formula C15H26O
Molecular Weight 222.3663
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Sources: Annalen der Chemie, Justus Liebigs (1949), 564, 141-51.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases.
2006 Oct 15
Patents

Patents

Sample Use Guides

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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:55:28 UTC 2023
Edited
by admin
on Fri Dec 15 17:55:28 UTC 2023
Record UNII
HHH8CPR1M2
Record Status Validated (UNII)
Record Version
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Name Type Language
PATCHOULI ALCOHOL
MI  
Common Name English
(-)-PATCHOULOL
Common Name English
PATCHOULI ALCOHOL [MI]
Common Name English
1,6-METHANONAPHTHALEN-1.BETA.(2H)-OL, 3,4,4A.BETA.,5,6.BETA.,7,8,8A-OCTAHYDRO-4.ALPHA.,8A.BETA.,9,9-TETRAMETHYL-
Common Name English
1,6-METHANONAPHTHALEN-1(2H)-OL, OCTAHYDRO-4,8A,9,9-TETRAMETHYL-, (1R,4S,4AS,6R,8AS)-
Common Name English
(-)-PATCHOULI ALCOHOL
Common Name English
1,6-METHANONAPHTHALEN-1(2H)-OL, OCTAHYDRO-4,8A,9,9-TETRAMETHYL-, (1R-(1.ALPHA.,4.BETA.,4A.ALPHA.,6.BETA.,8A.ALPHA.))-
Common Name English
PATCHOULI CAMPHOR
Common Name English
PATCHOULOL
Common Name English
Code System Code Type Description
CAS
5986-55-0
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-807-2
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
CHEBI
7940
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
PUBCHEM
10955174
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
WIKIPEDIA
PATCHOULOL
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
FDA UNII
HHH8CPR1M2
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID9052266
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY
MERCK INDEX
m8427
Created by admin on Fri Dec 15 17:55:28 UTC 2023 , Edited by admin on Fri Dec 15 17:55:28 UTC 2023
PRIMARY Merck Index