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
CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1
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 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | TIMEWISE REPAIR VOLU-FIRM EYE RENEWAL CREAM Approved UseUnknown Launch Date2017 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
5 % single, topical Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Contact dematitis... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Contact dematitis | 5 % single, topical Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hypotensive activity of terpenes found in essential oils. | 2010-12-09 |
|
| Antigenotoxic effect of Chamomilla recutita (L.) Rauschert essential oil in mouse spermatogonial cells, and determination of its antioxidant capacity in vitro. | 2010-09-30 |
|
| Whitening effect of alpha-bisabolol in Asian women subjects. | 2010-08 |
|
| alpha-Bisabolol induces dose- and time-dependent apoptosis in HepG2 cells via a Fas- and mitochondrial-related pathway, involves p53 and NFkappaB. | 2010-07-15 |
|
| Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines. | 2010-07 |
|
| Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. | 2010-05-15 |
|
| Differentiating and apoptotic dose-dependent effects in (-)-alpha-bisabolol-treated human endothelial cells. | 2010-04-23 |
|
| Volatile compounds of flowers and leaves of Sideritis italica (Miller) Greuter et Burdet (Lamiaceae), a plant used as mountain tea. | 2010-04 |
|
| Composition and biological activity of the essential oil from leaves of Plinia cerrocampanensis, a new source of alpha-bisabolol. | 2010-04 |
|
| Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate. | 2010-03-31 |
|
| Evaluation of the sesquiterpene (-)-alpha-bisabolol as a novel peripheral nervous blocker. | 2010-03-12 |
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| Reactions to Aquaphor: is bisabolol the culprit? | 2010-03-05 |
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| Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions. | 2010-03 |
|
| Effect of German chamomile oil application on alleviating atopic dermatitis-like immune alterations in mice. | 2010-03 |
|
| Activity of (-)alpha-bisabolol against Leishmania infantum promastigotes. | 2010-03 |
|
| Bisabolol. | 2010-02-09 |
|
| Essential oil from the underground parts of Laserpitium zernyi: potential source of alpha-bisabolol and its antimicrobial activity. | 2010-02 |
|
| Gastroprotection of (-)-alpha-bisabolol on acute gastric mucosal lesions in mice: the possible involved pharmacological mechanisms. | 2010-02 |
|
| 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. | 2010-01 |
|
| In vivo effect of alpha-bisabolol, a nontoxic sesquiterpene alcohol, on the induction of spontaneous mammary tumors in HER-2/neu transgenic mice. | 2010 |
|
| 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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| Bisabolol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide, and KATP+ channels. | 2009-12 |
|
| Validation of a high-performance liquid chromatography method for the determination of (-)-alpha-bisabolol from particulate systems. | 2009-09 |
|
| Involvement of mitochondrial permeability transition pore opening in alpha-bisabolol induced apoptosis. | 2009-08 |
|
| Plant antimicrobial agents and their effects on plant and human pathogens. | 2009-07-31 |
|
| Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis. | 2009-04-29 |
|
| Observational study: Matricaria chamomilla may improve some symptoms of attention-deficit hyperactivity disorder. | 2009-04 |
|
| Gastroprotective mechanism of Vanillosmopsis arborea bark essential oil. | 2009-01 |
|
| Antioxidant activity of bisabolol: inhibitory effects on chemiluminescence of human neutrophil bursts and cell-free systems. | 2009 |
|
| Mechanisms of depigmentation by alpha-bisabolol. | 2008-12 |
|
| Fragrance material review on alpha-bisabolol. | 2008-11 |
|
| Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid. | 2008-08-15 |
|
| Skin protection creams in medical settings: successful or evil? | 2008-07-25 |
|
| Contact cheilitis from bisabolol and polyvinylpyrrolidone/hexadecene copolymer in lipstick. | 2008-03 |
|
| Treatment of mild to moderate seborrhoeic dermatitis with MAS064D (Sebclair), a novel topical medical device: results of a pilot, randomized, double-blind, controlled trial. | 2008-03 |
|
| Chamomile: a spoonful of medicine. | 2008-01-04 |
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| Alpha-bisabolol: unexpected plant-derived weapon in the struggle against tumour survival? | 2007-12 |
|
| Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils. | 2007-10-17 |
|
| Novel eye cream containing a mixture of human growth factors and cytokines for periorbital skin rejuvenation. | 2007-07 |
|
| Synthetic organic chemistry based on small ring compounds. | 2007-07 |
|
| Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. | 2007-07 |
|
| Anti-irritants II: Efficacy against cumulative irritation. | 2006-09 |
|
| Anti-irritants I: Dose-response in acute irritation. | 2006-09 |
|
| 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.). | 2006-08-17 |
|
| The hairless guinea-pig as a model for treatment of acute irritation in humans. | 2006-08 |
|
| Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine. | 2006-04 |
|
| The hairless guinea-pig as a model for treatment of cumulative irritation in humans. | 2006-02 |
|
| Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica. | 2006-01-11 |
|
| Bisabolane- and santalane-type sesquiterpenoids from Santalum album of Indian origin. | 2005-12 |
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
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Edited
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| Record UNII |
24WE03BX2T
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| Record Status |
Validated (UNII)
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m2515
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Matricaria recutita flower head.
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ACTIVE MOIETY |