U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of LEVOMENOL

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

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q969F8
Gene ID: 84634.0
Gene Symbol: KISS1R
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
TIMEWISE REPAIR VOLU-FIRM EYE RENEWAL CREAM

Approved Use

Unknown

Launch Date

1.51070402E12
PubMed

PubMed

TitleDatePubMed
Determination of the ploidy level in chamomile (Chamomilla recutita (L.) Rausch.) strains rich in alpha-bisabolol.
2003
[Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis].
2003 Jan-Mar
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
2004 Dec
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
Chemical composition and insecticidal activity of essential oils from Vanillosmopsis pohlii baker against Bemisia argentifolii.
2004 Sep 22
Evaluation of mutagenic and antimutagenic activities of alpha-bisabolol in the Salmonella/microsome assay.
2005 Aug 1
Bisabolane- and santalane-type sesquiterpenoids from Santalum album of Indian origin.
2005 Dec
Daucane sesquiterpenes from Ferula hermonis.
2005 Mar
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.
2006 Apr
The hairless guinea-pig as a model for treatment of acute irritation in humans.
2006 Aug
The hairless guinea-pig as a model for treatment of cumulative irritation in humans.
2006 Feb
Synthesis of beta-bisabolol by ring-closing olefin metathesis reaction.
2006 Jan
Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica.
2006 Jan 11
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
Anti-irritants II: Efficacy against cumulative irritation.
2006 Sep
Anti-irritants I: Dose-response in acute irritation.
2006 Sep
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
Synthetic organic chemistry based on small ring compounds.
2007 Jul
Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus.
2007 Jul
Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.
2007 Oct 17
Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid.
2008 Aug 15
Mechanisms of depigmentation by alpha-bisabolol.
2008 Dec
Chamomile: a spoonful of medicine.
2008 Jan-Feb
Skin protection creams in medical settings: successful or evil?
2008 Jul 25
Contact cheilitis from bisabolol and polyvinylpyrrolidone/hexadecene copolymer in lipstick.
2008 Mar
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
Observational study: Matricaria chamomilla may improve some symptoms of attention-deficit hyperactivity disorder.
2009 Apr
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
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
Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.
2010
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
Gastroprotection of (-)-alpha-bisabolol on acute gastric mucosal lesions in mice: the possible involved pharmacological mechanisms.
2010 Feb
Bisabolol.
2010 Jan-Feb
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
Activity of (-)alpha-bisabolol against Leishmania infantum promastigotes.
2010 Mar
Evaluation of the sesquiterpene (-)-alpha-bisabolol as a novel peripheral nervous blocker.
2010 Mar 12
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
2010 May 15
Patents

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.
Name Type Language
LEVOMENOL
INN   MART.   USP-RS   WHO-DD  
INN  
Official Name English
BISABOLOL
INCI   VANDF  
INCI  
Official Name English
LEVOMENOL [WHO-DD]
Common Name English
5-HEPTEN-2-OL, 6-METHYL-2-(4- METHYL-3-CYCLOHEXEN-1-YL), (-)-
Common Name English
LEVOMENOL [MART.]
Common Name English
.ALPHA.-BISABOLOL (-)-FORM [MI]
Common Name English
(-)-6-METHYL-2-(4-METHYL-3-CYCLOHEXEN-1-YL)-5-HEPTEN-2-OL
Systematic Name English
3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL-3-PENTEN-1-YL)-, (.ALPHA.S,1S)-
Common Name English
FEMA NO. 4666
Code English
BISABOLOL, (-)-.ALPHA.
Common Name English
.ALPHA.-BISABOLOL, (-)-
Common Name English
(-)-.ALPHA.-BISABOLOL (CONSTITUENT OF CHAMOMILE) [DSC]
Common Name English
KAMILLOSAN
Common Name English
BISABOLOL [VANDF]
Common Name English
(.ALPHA.S,1S)-.ALPHA.-BISABOLOL
Common Name English
BISABOLOL [INCI]
Common Name English
LEVOMENOL [INN]
Common Name English
(-)-.ALPHA.-BISABOLOL
Common Name English
ALPHA-(-)-BISABOLOL
Common Name English
LEVOMENOL [USP-RS]
Common Name English
.ALPHA.-BISABOLOL
Common Name English
Code System Code Type Description
MERCK INDEX
M2515
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY Merck Index
INN
3667
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
EVMPD
SUB79626
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
DRUG CENTRAL
4619
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-423-3
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
RXCUI
19461
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
ALTERNATIVE RxNorm
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
CONCEPT Industrial Aid
ChEMBL
CHEMBL2104360
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
FDA UNII
24WE03BX2T
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
MESH
C004497
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
CAS
23089-26-1
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
DRUG BANK
DB13153
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
EPA CompTox
23089-26-1
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
WIKIPEDIA
BISABOLOL
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
PUBCHEM
442343
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
EVMPD
SUB08474MIG
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
USP_CATALOG
1362307
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C80904
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY
RXCUI
1306126
Created by admin on Sat Jun 26 04:14:07 UTC 2021 , Edited by admin on Sat Jun 26 04:14:07 UTC 2021
PRIMARY