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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
Structure of LEVOMENOL

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

HIDE SMILES / InChI

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

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

2017
PubMed

PubMed

TitleDatePubMed
Volatile secondary metabolite pattern of callus cultures of Chamomilla recutita.
2001
[Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis].
2003 Jan-Mar
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
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.
2006 Apr
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
Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid.
2008 Aug 15
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
Bisabolol.
2010 Jan-Feb
Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines.
2010 Jul
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:39 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:39 GMT 2023
Record UNII
24WE03BX2T
Record Status Validated (UNII)
Record Version
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Name Type Language
LEVOMENOL
INN   MART.   USP-RS   WHO-DD  
INN  
Official Name English
BISABOLOL
INCI   VANDF  
INCI  
Official Name English
5-HEPTEN-2-OL, 6-METHYL-2-(4- METHYL-3-CYCLOHEXEN-1-YL), (-)-
Common Name English
Levomenol [WHO-DD]
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 Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY Merck Index
INN
3667
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
DAILYMED
24WE03BX2T
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
EVMPD
SUB79626
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
DRUG CENTRAL
4619
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-423-3
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
RXCUI
19461
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
ALTERNATIVE RxNorm
RS_ITEM_NUM
1362307
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
CONCEPT Industrial Aid
SMS_ID
100000082277
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104360
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
FDA UNII
24WE03BX2T
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
JECFA MONOGRAPH
2009
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
MESH
C004497
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
CAS
23089-26-1
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
DRUG BANK
DB13153
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID4042094
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
WIKIPEDIA
BISABOLOL
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
PUBCHEM
442343
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
EVMPD
SUB08474MIG
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
NCI_THESAURUS
C80904
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
RXCUI
1306126
Created by admin on Fri Dec 15 16:11:39 GMT 2023 , Edited by admin on Fri Dec 15 16:11:39 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Matricaria recutita flower head.
PARENT -> CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY