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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Chemical composition of the essential oils of Clausena lansium from Hainan Island, China. | 2004 Mar-Apr |
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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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Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis. | 2009 Apr 29 |
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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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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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Gastroprotection of (-)-alpha-bisabolol on acute gastric mucosal lesions in mice: the possible involved pharmacological mechanisms. | 2010 Feb |
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Activity of (-)alpha-bisabolol against Leishmania infantum promastigotes. | 2010 Mar |
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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BISABOLOL
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ACTIVE MOIETY