Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H26O |
Molecular Weight | 222.3663 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C
InChI
InChIKey=RGZSQWQPBWRIAQ-CABCVRRESA-N
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
Molecular Formula | C15H26O |
Molecular Weight | 222.3663 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Levomenol, or more formally α-(−)-bisabolol or (-)-alpha-bisabolol was identified as a major constituent of Salvia runcinata essential oil, a plant indigenous to South Africa. This compound exhibits pharmacological properties such as analgesic, antibiotic and anticancer activities. Mutagenicity and genotoxicity of bisabolol have also been investigated. Due to the low toxicity associated with bisabolol the Food and Drug Administration (FDA) has granted this constituent with Generally Regarded as Safe (GRAS) status, which has promoted its use as an active ingredient in several commercial products. Recently provided experiments have shown the anti-amyloidogenic potential and anti-apoptotic property of the α-bisabolol against Aβ25-35 induced neurotoxicity in PC12 cells. This compound prevented the oligomers formation as well as disaggregates the matured fibrils. It is known, that of the multiple etiological factors of Alzheimer's disease (AD), the accumulation of senile plaques (SPs) particularly as Aβ oligomers correlates with the relentlessness cognitive impairment in AD patients and play a vital role in AD pathology. As a conclusion obtained properties of α-bisabolol allowed suggesting, that this compound could be used as an excellent therapeutic drug to combat AD. Besides, anti-cancer activity of α-bisabolol was also studied. α-Bisabolol inhibited invasiveness and motility in pancreatic cancer through kisspeptin 1 receptor (KISS1R) activation. Further investigations are necessary to clarify the precise mechanisms of α-bisabolol activity for clinical application as a novel treatment for pancreatic cancer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q969F8 Gene ID: 84634.0 Gene Symbol: KISS1R Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26851012 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Preventing | TIMEWISE REPAIR VOLU-FIRM EYE RENEWAL CREAM Approved UseUnknown Launch Date2017 |
PubMed
Title | Date | PubMed |
---|---|---|
Volatile secondary metabolite pattern of callus cultures of Chamomilla recutita. | 2001 |
|
[Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis]. | 2003 Jan-Mar |
|
Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods. | 2004 Dec 5 |
|
New terpenoids in cultivated and wild chamomile (in vivo and in vitro). | 2004 Feb 5 |
|
alpha-Bisabolol, a nontoxic natural compound, strongly induces apoptosis in glioma cells. | 2004 Mar 12 |
|
Chemical composition of the essential oils of Clausena lansium from Hainan Island, China. | 2004 Mar-Apr |
|
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine. | 2006 Apr |
|
Alpha-bisabolol: unexpected plant-derived weapon in the struggle against tumour survival? | 2007 Dec |
|
Novel eye cream containing a mixture of human growth factors and cytokines for periorbital skin rejuvenation. | 2007 Jul |
|
Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid. | 2008 Aug 15 |
|
Treatment of mild to moderate seborrhoeic dermatitis with MAS064D (Sebclair), a novel topical medical device: results of a pilot, randomized, double-blind, controlled trial. | 2008 Mar |
|
Fragrance material review on alpha-bisabolol. | 2008 Nov |
|
Antioxidant activity of bisabolol: inhibitory effects on chemiluminescence of human neutrophil bursts and cell-free systems. | 2009 |
|
Bisabolol. | 2010 Jan-Feb |
|
Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29243833
antinociceptive and anti-inflammatory effects in rats: at different times before the formalin insult, animals were orally administered with vehicles or increasing doses of diclofenac (10, 18, 30, and 56 mg/kg at 30 min before), bisabolol (30, 56, 100, and 180 mg/kg at 60 min before), or the diclofenac – bisabolol combinations (12.4, 24.7, 49.5, and 98.9 mg/kg).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29150331
It was investigated the anti-amyloidogenic potential and anti-apoptotic property of the α-bisabolol against Aβ25-35 induced neurotoxicity in PC12 cells. Treatment with α-bisabolol (5 μg/ml) after 24 h incubation with Aβ25-35 reduced the aggregation propensity of Aβ (p < 0.05), as observed by the reduced fluorescence intensity of thioflavin T (ThT). The results of antiaggregation and disaggregation assay showed an increase in fluorescence intensity in Aβ treated group, whereas the co-treatment of α-bisabolol (5 μg/ml) with Aβ25-35 showed an extensive decrease in the fluorescence intensity, which suggests that α-bisabolol prevents the oligomers formation as well as disaggregates the matured fibrils.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:11:39 GMT 2023
by
admin
on
Fri Dec 15 16:11:39 GMT 2023
|
Record UNII |
24WE03BX2T
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
m2515
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | Merck Index | ||
|
3667
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
24WE03BX2T
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
SUB79626
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
4619
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
245-423-3
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
19461
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
ALTERNATIVE | RxNorm | ||
|
1362307
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
C45678
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
CONCEPT | Industrial Aid | ||
|
100000082277
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
CHEMBL2104360
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
24WE03BX2T
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
2009
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
C004497
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
23089-26-1
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
DB13153
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
DTXSID4042094
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
BISABOLOL
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
442343
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
SUB08474MIG
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
C80904
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY | |||
|
1306126
Created by
admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Matricaria recutita flower head.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |