Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H26O |
| Molecular Weight | 222.3669 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=CCC[C@@](C)([C@]1([H])CC=C(C)CC1)O)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 | 222.3669 |
| 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) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
|||
| Preventing | TIMEWISE REPAIR VOLU-FIRM EYE RENEWAL CREAM Approved UseUnknown Launch Date1.51070402E12 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis]. | 2003 Jan-Mar |
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| Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures. | 2004 Dec |
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| Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods. | 2004 Dec 5 |
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| New terpenoids in cultivated and wild chamomile (in vivo and in vitro). | 2004 Feb 5 |
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| alpha-Bisabolol, a nontoxic natural compound, strongly induces apoptosis in glioma cells. | 2004 Mar 12 |
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| Chemical composition of the essential oils of Clausena lansium from Hainan Island, China. | 2004 Mar-Apr |
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| Chemical composition and insecticidal activity of essential oils from Vanillosmopsis pohlii baker against Bemisia argentifolii. | 2004 Sep 22 |
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| Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine. | 2006 Apr |
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| The hairless guinea-pig as a model for treatment of acute irritation in humans. | 2006 Aug |
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| Synthesis of beta-bisabolol by ring-closing olefin metathesis reaction. | 2006 Jan |
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| Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica. | 2006 Jan 11 |
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| Headspace-solid-phase microextraction fast GC in combination with principal component analysis as a tool to classify different chemotypes of chamomile flower-heads (Matricaria recutita l.). | 2006 Jul-Aug |
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| Anti-irritants II: Efficacy against cumulative irritation. | 2006 Sep |
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| Anti-irritants I: Dose-response in acute irritation. | 2006 Sep |
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| Novel eye cream containing a mixture of human growth factors and cytokines for periorbital skin rejuvenation. | 2007 Jul |
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| Synthetic organic chemistry based on small ring compounds. | 2007 Jul |
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| Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. | 2007 Jul |
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| Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils. | 2007 Oct 17 |
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| Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid. | 2008 Aug 15 |
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| Chamomile: a spoonful of medicine. | 2008 Jan-Feb |
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| Skin protection creams in medical settings: successful or evil? | 2008 Jul 25 |
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| Contact cheilitis from bisabolol and polyvinylpyrrolidone/hexadecene copolymer in lipstick. | 2008 Mar |
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| 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 |
|
| Antioxidant activity of bisabolol: inhibitory effects on chemiluminescence of human neutrophil bursts and cell-free systems. | 2009 |
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| Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis. | 2009 Apr 29 |
|
| Involvement of mitochondrial permeability transition pore opening in alpha-bisabolol induced apoptosis. | 2009 Aug |
|
| Bisabolol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide, and KATP+ channels. | 2009 Dec |
|
| Gastroprotective mechanism of Vanillosmopsis arborea bark essential oil. | 2009 Jan |
|
| Plant antimicrobial agents and their effects on plant and human pathogens. | 2009 Jul 31 |
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| Validation of a high-performance liquid chromatography method for the determination of (-)-alpha-bisabolol from particulate systems. | 2009 Sep |
|
| In vivo effect of alpha-bisabolol, a nontoxic sesquiterpene alcohol, on the induction of spontaneous mammary tumors in HER-2/neu transgenic mice. | 2010 |
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| Concise synthesis of an antifeedant sesquiterpene against Locusta migratoria. | 2010 |
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| Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries. | 2010 |
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| Volatile compounds of flowers and leaves of Sideritis italica (Miller) Greuter et Burdet (Lamiaceae), a plant used as mountain tea. | 2010 Apr |
|
| Composition and biological activity of the essential oil from leaves of Plinia cerrocampanensis, a new source of alpha-bisabolol. | 2010 Apr |
|
| Differentiating and apoptotic dose-dependent effects in (-)-alpha-bisabolol-treated human endothelial cells. | 2010 Apr 23 |
|
| Whitening effect of alpha-bisabolol in Asian women subjects. | 2010 Aug |
|
| Essential oil from the underground parts of Laserpitium zernyi: potential source of alpha-bisabolol and its antimicrobial activity. | 2010 Feb |
|
| Evaluation of the effects of galbanic acid from Ferula szowitsiana and conferol from F. badrakema, as modulators of multi-drug resistance in clinical isolates of Escherichia coli and Staphylococcus aureus. | 2010 Jan |
|
| Reactions to Aquaphor: is bisabolol the culprit? | 2010 Jan-Feb |
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| Bisabolol. | 2010 Jan-Feb |
|
| Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines. | 2010 Jul |
|
| alpha-Bisabolol induces dose- and time-dependent apoptosis in HepG2 cells via a Fas- and mitochondrial-related pathway, involves p53 and NFkappaB. | 2010 Jul 15 |
|
| Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions. | 2010 Mar |
|
| Effect of German chamomile oil application on alleviating atopic dermatitis-like immune alterations in mice. | 2010 Mar |
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| Evaluation of the sesquiterpene (-)-alpha-bisabolol as a novel peripheral nervous blocker. | 2010 Mar 12 |
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| Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate. | 2010 Mar 31 |
|
| Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. | 2010 May 15 |
|
| Antigenotoxic effect of Chamomilla recutita (L.) Rauschert essential oil in mouse spermatogonial cells, and determination of its antioxidant capacity in vitro. | 2010 Sep 30 |
|
| Hypotensive activity of terpenes found in essential oils. | 2010 Sep-Oct |
Sample Use Guides
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
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
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admin
on
Edited
Sat Jun 26 04:14:07 UTC 2021
by
admin
on
Sat Jun 26 04:14:07 UTC 2021
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| Record UNII |
24WE03BX2T
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| Record Status |
Validated (UNII)
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M2515
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PRIMARY | Merck Index | ||
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3667
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SUB79626
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245-423-3
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19461
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C45678
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CONCEPT | Industrial Aid | ||
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CHEMBL2104360
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24WE03BX2T
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C004497
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23089-26-1
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23089-26-1
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BISABOLOL
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1362307
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C80904
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1306126
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Matricaria recutita flower head.
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ACTIVE MOIETY |
