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
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 |
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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 |
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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 |
PubMed
Title | Date | PubMed |
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Volatile secondary metabolite pattern of callus cultures of Chamomilla recutita. | 2001 |
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(+)-epi-Alpha-bisabolol [correction of bisbolol] is the wound-healing principle of Peperomia galioides: investigation of the in vivo wound-healing activity of related terpenoids. | 2001 Oct |
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Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-alpha-bisabolol and (-)-8-epi-alpha-bisabolol. | 2003 Feb 24 |
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The ability of Bipolaris sorokiniana to modify geraniol and (-)-alpha-bisabolol as exogenous substrates. | 2003 Jun |
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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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Chemical composition of the essential oils of Clausena lansium from Hainan Island, China. | 2004 Mar-Apr |
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Evaluation of mutagenic and antimutagenic activities of alpha-bisabolol in the Salmonella/microsome assay. | 2005 Aug 1 |
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Bisabolane- and santalane-type sesquiterpenoids from Santalum album of Indian origin. | 2005 Dec |
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Daucane sesquiterpenes from Ferula hermonis. | 2005 Mar |
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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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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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Anti-irritants II: Efficacy against cumulative irritation. | 2006 Sep |
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Alpha-bisabolol: unexpected plant-derived weapon in the struggle against tumour survival? | 2007 Dec |
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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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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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Mechanisms of depigmentation by alpha-bisabolol. | 2008 Dec |
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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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Fragrance material review on alpha-bisabolol. | 2008 Nov |
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Observational study: Matricaria chamomilla may improve some symptoms of attention-deficit hyperactivity disorder. | 2009 Apr |
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Bisabolol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide, and KATP+ channels. | 2009 Dec |
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Gastroprotective mechanism of Vanillosmopsis arborea bark essential oil. | 2009 Jan |
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Plant antimicrobial agents and their effects on plant and human pathogens. | 2009 Jul 31 |
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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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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 |
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Differentiating and apoptotic dose-dependent effects in (-)-alpha-bisabolol-treated human endothelial cells. | 2010 Apr 23 |
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Whitening effect of alpha-bisabolol in Asian women subjects. | 2010 Aug |
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Essential oil from the underground parts of Laserpitium zernyi: potential source of alpha-bisabolol and its antimicrobial activity. | 2010 Feb |
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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 |
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Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines. | 2010 Jul |
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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 |
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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 |
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Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. | 2010 May 15 |
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Antigenotoxic effect of Chamomilla recutita (L.) Rauschert essential oil in mouse spermatogonial cells, and determination of its antioxidant capacity in vitro. | 2010 Sep 30 |
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.
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m2515
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C45678
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BISABOLOL
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ACTIVE MOIETY