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23089-26-1,MFCD03412455
Catalog No.:AA00I4FY

23089-26-1 | 3-Cyclohexene-1-methanol, a,4-dimethyl-a-(4-methyl-3-pentenyl)-,(aS,1S)-

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10mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00I4FY
Chemical Name:
3-Cyclohexene-1-methanol, a,4-dimethyl-a-(4-methyl-3-pentenyl)-,(aS,1S)-
CAS Number:
23089-26-1
Molecular Formula:
C15H26O
Molecular Weight:
222.3663
MDL Number:
MFCD03412455
SMILES:
CC(=CCC[C@@]([C@H]1CCC(=CC1)C)(O)C)C
FEMA Number:
4666
Properties
Computed Properties
 
Complexity:
284  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
4  
XLogP3:
3.8  

Literature

Title: An untargeted metabolomic approach in the chemotaxonomic assessment of two Salvia species as a potential source of α-bisabolol.

Journal: Phytochemistry 20121201

Title: Molecular cloning and characterization of (+)-epi-α-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis.

Journal: Archives of biochemistry and biophysics 20121101

Title: Enhanced topical delivery of small hydrophilic or lipophilic active agents and epidermal growth factor by fractional radiofrequency microporation.

Journal: Pharmaceutical research 20120701

Title: Guaianolides and volatile compounds in chamomile tea.

Journal: Plant foods for human nutrition (Dordrecht, Netherlands) 20120601

Title: In vitro and in vivo antimalarial activity of essential oils and chemical components from three medicinal plants found in northeastern Brazil.

Journal: Planta medica 20120501

Title: Activity of Matricaria chamomilla essential oil against anisakiasis.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20120415

Title: STAT-3 inhibitory bisabolanes from Carthamus glaucus.

Journal: Journal of natural products 20120323

Title: Psychopharmacological profile of Chamomile (Matricaria recutita L.) essential oil in mice.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20120215

Title: Essential oil from aerial parts of of Betonica grandiflora Willd. from Iran.

Journal: Natural product research 20120101

Title: Chemical and allelopathic analyses of essential oils of Prangos pabularia Lindl. from Iran.

Journal: Natural product research 20120101

Title: In-vitro characterization of the pharmacological effects induced by (-)-α-bisabolol in rat smooth muscle preparations.

Journal: Canadian journal of physiology and pharmacology 20120101

Title: α-bisabolol is an effective proapoptotic agent against BCR-ABL(+) cells in synergism with Imatinib and Nilotinib.

Journal: PloS one 20120101

Title: Anti-nociceptive and anti-inflammatory activities of (-)-α-bisabolol in rodents.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20111201

Title: Antitumor effects of α-bisabolol against pancreatic cancer.

Journal: Cancer science 20111201

Title: (-)-α-Bisabolol-induced gastroprotection is associated with reduction in lipid peroxidation, superoxide dismutase activity and neutrophil migration.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20111120

Title: Genome mining reveals two novel bacterial sesquiterpene cyclases: (-)-germacradien-4-ol and (-)-epi-α-bisabolol synthases from Streptomyces citricolor.

Journal: Chembiochem : a European journal of chemical biology 20111017

Title: Inhibitory effects of (-)-α-bisabolol on LPS-induced inflammatory response in RAW264.7 macrophages.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111001

Title: Disulphides in the volatile oil of Ferula behboudiana Rech. f. & Esfand.

Journal: Natural product research 20111001

Title: Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.

Journal: Phytochemistry 20110801

Title: Evaluation of the mutagenicity of sesquiterpenic compounds and their influence on the susceptibility towards antibiotics of two clinically relevant bacterial strains.

Journal: Mutation research 20110714

Title: Effect of topical heparin and levomenol on atopic dermatitis: a randomized four-arm, placebo-controlled, double-blind clinical study.

Journal: Journal of the European Academy of Dermatology and Venereology : JEADV 20110601

Title: Chemical variation of the essential oil of Prangos uloptera DC. at different stages of growth.

Journal: Natural product research 20110401

Title: (-)-α-Bisabolol attenuates visceral nociception and inflammation in mice.

Journal: Fitoterapia 20110301

Title: Antigenotoxicity, cytotoxicity, and apoptosis induction by apigenin, bisabolol, and protocatechuic acid.

Journal: Journal of medicinal food 20110301

Title: Compositae-associated allergic contact dermatitis from bisabolol.

Journal: Dermatitis : contact, atopic, occupational, drug 20110101

Title: Pro-apoptotic activity of α-bisabolol in preclinical models of primary human acute leukemia cells.

Journal: Journal of translational medicine 20110101

Title: Desert farming benefits from microbial potential in arid soils and promotes diversity and plant health.

Journal: PloS one 20110101

Title: The in-vitro evaluation of antibacterial, antifungal and cytotoxic properties of Marrubium vulgare L. essential oil grown in Tunisia.

Journal: Lipids in health and disease 20110101

Title: Chamomile (Matricaria chamomilla L.): An overview.

Journal: Pharmacognosy reviews 20110101

Title: Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery.

Journal: BMC complementary and alternative medicine 20110101

Title: Is propolis safe as an alternative medicine?

Journal: Journal of pharmacy & bioallied sciences 20110101

Title: Enhancement of the antibiotic activity of erythromycin by volatile compounds of Lippia alba (Mill.) N.E. Brown against Staphylococcus aureus.

Journal: Pharmacognosy magazine 20110101

Title: Whitening effect of alpha-bisabolol in Asian women subjects.

Journal: International journal of cosmetic science 20100801

Title: alpha-Bisabolol induces dose- and time-dependent apoptosis in HepG2 cells via a Fas- and mitochondrial-related pathway, involves p53 and NFkappaB.

Journal: Biochemical pharmacology 20100715

Title: Antitumor activity of (-)-alpha-bisabolol-based thiosemicarbazones against human tumor cell lines.

Journal: European journal of medicinal chemistry 20100701

Title: Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.

Journal: International journal of food microbiology 20100515

Title: Differentiating and apoptotic dose-dependent effects in (-)-alpha-bisabolol-treated human endothelial cells.

Journal: Journal of natural products 20100423

Title: Composition and biological activity of the essential oil from leaves of Plinia cerrocampanensis, a new source of alpha-bisabolol.

Journal: Bioresource technology 20100401

Title: Volatile compounds of flowers and leaves of Sideritis italica (Miller) Greuter et Burdet (Lamiaceae), a plant used as mountain tea.

Journal: Natural product research 20100401

Title: Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.

Journal: Journal of the American Chemical Society 20100331

Title: Evaluation of the sesquiterpene (-)-alpha-bisabolol as a novel peripheral nervous blocker.

Journal: Neuroscience letters 20100312

Title: Activity of (-)alpha-bisabolol against Leishmania infantum promastigotes.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20100301

Title: Effect of German chamomile oil application on alleviating atopic dermatitis-like immune alterations in mice.

Journal: Journal of veterinary science 20100301

Title: Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions.

Journal: Natural product communications 20100301

Title: Gastroprotection of (-)-alpha-bisabolol on acute gastric mucosal lesions in mice: the possible involved pharmacological mechanisms.

Journal: Fundamental & clinical pharmacology 20100201

Title: Essential oil from the underground parts of Laserpitium zernyi: potential source of alpha-bisabolol and its antimicrobial activity.

Journal: Natural product communications 20100201

Title: Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.

Journal: Natural product research 20100101

Title: Bisabolol.

Journal: Dermatitis : contact, atopic, occupational, drug 20100101

Title: Reactions to Aquaphor: is bisabolol the culprit?

Journal: Pediatric dermatology 20100101

Title: Concise synthesis of an antifeedant sesquiterpene against Locusta migratoria.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: In vivo effect of alpha-bisabolol, a nontoxic sesquiterpene alcohol, on the induction of spontaneous mammary tumors in HER-2/neu transgenic mice.

Journal: Oncology research 20100101

Title: Hypotensive activity of terpenes found in essential oils.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101

Title: Antigenotoxic effect of Chamomilla recutita (L.) Rauschert essential oil in mouse spermatogonial cells, and determination of its antioxidant capacity in vitro.

Journal: International journal of molecular sciences 20100101

Title: 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.

Journal: Research in pharmaceutical sciences 20100101

Title: Bisabolol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide, and KATP+ channels.

Journal: Journal of medicinal food 20091201

Title: Validation of a high-performance liquid chromatography method for the determination of (-)-alpha-bisabolol from particulate systems.

Journal: Biomedical chromatography : BMC 20090901

Title: Involvement of mitochondrial permeability transition pore opening in alpha-bisabolol induced apoptosis.

Journal: The FEBS journal 20090801

Title: Plant antimicrobial agents and their effects on plant and human pathogens.

Journal: International journal of molecular sciences 20090801

Title: Observational study: Matricaria chamomilla may improve some symptoms of attention-deficit hyperactivity disorder.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20090401

Title: Gastroprotective mechanism of Vanillosmopsis arborea bark essential oil.

Journal: Fitoterapia 20090101

Title: Antioxidant activity of bisabolol: inhibitory effects on chemiluminescence of human neutrophil bursts and cell-free systems.

Journal: Pharmacology 20090101

Title: Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis.

Journal: Annals of clinical microbiology and antimicrobials 20090101

Title: Mechanisms of depigmentation by alpha-bisabolol.

Journal: Journal of dermatological science 20081201

Title: Fragrance material review on alpha-bisabolol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081101

Title: Insight into the apoptosis-inducing action of alpha-bisabolol towards malignant tumor cells: involvement of lipid rafts and Bid.

Journal: Archives of biochemistry and biophysics 20080815

Title: Treatment of mild to moderate seborrhoeic dermatitis with MAS064D (Sebclair), a novel topical medical device: results of a pilot, randomized, double-blind, controlled trial.

Journal: Journal of the European Academy of Dermatology and Venereology : JEADV 20080301

Title: Contact cheilitis from bisabolol and polyvinylpyrrolidone/hexadecene copolymer in lipstick.

Journal: Contact dermatitis 20080301

Title: Chamomile: a spoonful of medicine.

Journal: Holistic nursing practice 20080101

Title: Skin protection creams in medical settings: successful or evil?

Journal: Journal of occupational medicine and toxicology (London, England) 20080101

Title: Alpha-bisabolol: unexpected plant-derived weapon in the struggle against tumour survival?

Journal: The Italian journal of biochemistry 20071201

Title: Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.

Journal: Journal of agricultural and food chemistry 20071017

Title: Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus.

Journal: Antonie van Leeuwenhoek 20070701

Title: Synthetic organic chemistry based on small ring compounds.

Journal: Chemical & pharmaceutical bulletin 20070701

Title: Novel eye cream containing a mixture of human growth factors and cytokines for periorbital skin rejuvenation.

Journal: Journal of drugs in dermatology : JDD 20070701

Title: Anti-irritants I: Dose-response in acute irritation.

Journal: Contact dermatitis 20060901

Title: Anti-irritants II: Efficacy against cumulative irritation.

Journal: Contact dermatitis 20060901

Title: The hairless guinea-pig as a model for treatment of acute irritation in humans.

Journal: Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI) 20060801

Title: Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.

Journal: Journal of dermatological science 20060401

Title: The hairless guinea-pig as a model for treatment of cumulative irritation in humans.

Journal: Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI) 20060201

Title: Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica.

Journal: Journal of agricultural and food chemistry 20060111

Title: Synthesis of beta-bisabolol by ring-closing olefin metathesis reaction.

Journal: Natural product research 20060101

Title: 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.).

Journal: Phytochemical analysis : PCA 20060101

Title: Bisabolane- and santalane-type sesquiterpenoids from Santalum album of Indian origin.

Journal: Journal of natural products 20051201

Title: Evaluation of mutagenic and antimutagenic activities of alpha-bisabolol in the Salmonella/microsome assay.

Journal: Mutation research 20050801

Title: Daucane sesquiterpenes from Ferula hermonis.

Journal: Journal of natural products 20050301

Title: Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20041205

Title: Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.

Journal: Journal of the American College of Nutrition 20041201

Title: Chemical composition and insecticidal activity of essential oils from Vanillosmopsis pohlii baker against Bemisia argentifolii.

Journal: Journal of agricultural and food chemistry 20040922

Title: alpha-Bisabolol, a nontoxic natural compound, strongly induces apoptosis in glioma cells.

Journal: Biochemical and biophysical research communications 20040312

Title: New terpenoids in cultivated and wild chamomile (in vivo and in vitro).

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040205

Title: Chemical composition of the essential oils of Clausena lansium from Hainan Island, China.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101

Title: The ability of Bipolaris sorokiniana to modify geraniol and (-)-alpha-bisabolol as exogenous substrates.

Journal: Applied microbiology and biotechnology 20030601

Title: Phase solubility studies of pure (-)-alpha-bisabolol and camomile essential oil with beta-cyclodextrin.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20030301

Title: Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-alpha-bisabolol and (-)-8-epi-alpha-bisabolol.

Journal: Angewandte Chemie (International ed. in English) 20030224

Title: Determination of the ploidy level in chamomile (Chamomilla recutita (L.) Rausch.) strains rich in alpha-bisabolol.

Journal: Journal of applied genetics 20030101

Title: [Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis].

Journal: Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20030101

Title: Inhibitory effect of chamomile essential oil on the sister chromatid exchanges induced by daunorubicin and methyl methanesulfonate in mouse bone marrow.

Journal: Toxicology letters 20020905

Title: (+)-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.

Journal: Journal of natural products 20011001

Title: Volatile secondary metabolite pattern of callus cultures of Chamomilla recutita.

Journal: Natural product letters 20010101

Title: Fernandes MYD, et al. (-)-α-bisabolol prevents neuronal damage and memory deficits through reduction of proinflammatory markers induced by permanent focal cerebral ischemia in mice. Eur J Pharmacol. 2019 Jan 5;842:270-280.

Title: Melo LT, et al. (-)-α-Bisabolol reduces nociception and trigeminal central sensitisation in acute orofacial neuropathic pain induced by infraorbital nerve injury. Life Sci. 2019 Jun 15;227:122-128.

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SDS
Tags:23089-26-1 Molecular Formula|23089-26-1 MDL|23089-26-1 SMILES|23089-26-1 3-Cyclohexene-1-methanol, a,4-dimethyl-a-(4-methyl-3-pentenyl)-,(aS,1S)-