NerolidolCAS# 7212-44-4 |
- (+)-Nerolidol
Catalog No.:BCC8219
CAS No.:142-50-7
- cis-Nerolidol
Catalog No.:BCN9148
CAS No.:3790-78-1
- trans-Nerolidol
Catalog No.:BCX1466
CAS No.:40716-66-3
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 7212-44-4 | SDF | Download SDF |
PubChem ID | 5284507 | Appearance | Oil |
Formula | C15H26O | M.Wt | 222.4 |
Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
Synonyms | 40716-66-3;Trans-Nerolidol | ||
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | (6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol | ||
SMILES | CC(=CCCC(=CCCC(C)(C=C)O)C)C | ||
Standard InChIKey | FQTLCLSUCSAZDY-SDNWHVSQSA-N | ||
Standard InChI | InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+ | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Nerolidol, a sesquiterpene used as a food-flavoring agent and currently under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs. Nerolidol shows anti-cancer, sedative, antiulcer, antifungal, and antifeeding effects. Nerolidol can inhibit the growth of Leishmania amazonensis, L. braziliensis, and L. chagasi promastigotes and L. amazonensis amastigotes with in vitro 50% inhibitory concentrations of 85, 74, 75, and 67 uM, respectively. |
Targets | Antifection | ROS |
In vitro | Anti-biofilm, anti-hemolysis, and anti-virulence activities of black pepper, cananga, myrrh oils, and nerolidol against Staphylococcus aureus.[Pubmed: 25027570]Appl Microbiol Biotechnol. 2014 Nov;98(22):9447-57.The long-term usage of antibiotics has resulted in the evolution of multidrug-resistant bacteria. Unlike antibiotics, anti-virulence approaches target bacterial virulence without affecting cell viability, which may be less prone to develop drug resistance. Staphylococcus aureus is a major human pathogen that produces diverse virulence factors, such as α-toxin, which is hemolytic. Also, biofilm formation of S. aureus is one of the mechanisms of its drug resistance.
Antileishmanial activity of the terpene nerolidol.[Pubmed: 15855481 ]Antimicrob Agents Chemother. 2005 May;49(5):1679-87.The activity of Nerolidol, a sesquiterpene used as a food-flavoring agent and currently under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs, was evaluated against Leishmania species.
Nerolidol: An antifeeding sesquiterpene alcohol for gypsy moth larvae fromMelaleuca leucadendron[Reference: WebLink]J.Chem. Ecol., 1980, 6(4):845-51.A systematic procedure is reported for the isolation of a feeding deterrent, (E,S)-Nerolidol (I), fromMelaleuca leucadendron leaves for the gypsy moth larvae. Testing of the related alcohols, farnesol (II) and geraniol (III) showed them to be deterrent, but the simpler isoprene-related compounds, 2-methyl-3-buten-2-ol andt-amyl alcohol were inactive. |
In vivo | Antioxidant effects of nerolidol in mice hippocampus after open field test.[Pubmed: 23765368]Neurochem Res. 2013 Sep;38(9):1861-70.The aim of this study was to evaluate the neuroprotective effects of Nerolidol in mice hippocampus against oxidative stress in neuronal cells compared to ascorbic acid (positive control) as well as evaluated the Nerolidol sedative effects by open field test compared to diazepam (positive control).
Inhibition of azoxymethane-induced neoplasia of the large bowel by 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene (nerolidol).[Pubmed: 1988176]Carcinogenesis. 1991 Jan;12(1):151-2.The inhibitory capacities of four terpenes on azoxymethane (AOM)-induced neoplasia of the large bowel and duodenum was studied in male F344 rats.
|
Animal Research | Antifungal effect of eugenol and nerolidol against Microsporum gypseum in a guinea pig model.[Pubmed: 17202684]Nerolidol, an antiulcer constituent from the essential oil of Baccharis dracunculifolia DC (Asteraceae).[Pubmed: 17913068]Z Naturforsch C. 2007 Jul-Aug;62(7-8):537-42.In this study, the antiulcerogenic effect of essential oil from Baccharis dracunculifolia was evaluated using the model of acute gastric lesions induced by ethanol.
Biol Pharm Bull. 2007 Jan;30(1):184-8.Essential oils have been widely used in anti-infectious application.
In the present study, we elucidated the antifungal activities of eugenol and Nerolidol isolated from Japanese cypress oil in a guinea pig model infected by Microsporum gypseum (M. gypseum).
|
Nerolidol Dilution Calculator
Nerolidol Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 4.4964 mL | 22.482 mL | 44.964 mL | 89.9281 mL | 112.4101 mL |
5 mM | 0.8993 mL | 4.4964 mL | 8.9928 mL | 17.9856 mL | 22.482 mL |
10 mM | 0.4496 mL | 2.2482 mL | 4.4964 mL | 8.9928 mL | 11.241 mL |
50 mM | 0.0899 mL | 0.4496 mL | 0.8993 mL | 1.7986 mL | 2.2482 mL |
100 mM | 0.045 mL | 0.2248 mL | 0.4496 mL | 0.8993 mL | 1.1241 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Prilocaine
Catalog No.:BCC4929
CAS No.:721-50-6
- Mastoparan X
Catalog No.:BCC5833
CAS No.:72093-22-2
- 5(6)-Carboxyfluorescein
Catalog No.:BCC8283
CAS No.:72088-94-9
- 6,2',4'-Trimethoxyflavone
Catalog No.:BCC3897
CAS No.:720675-74-1
- Spinosin
Catalog No.:BCN1644
CAS No.:72063-39-9
- Sepinol
Catalog No.:BCN4277
CAS No.:72061-63-3
- Lochnericine
Catalog No.:BCN4595
CAS No.:72058-36-7
- NHS-LC-Biotin
Catalog No.:BCC3579
CAS No.:72040-63-2
- Henryoside
Catalog No.:BCN4276
CAS No.:72021-23-9
- 2-Geranyl-4-isobutyrylphloroglucinol
Catalog No.:BCN7170
CAS No.:72008-03-8
- Chlorquinaldol
Catalog No.:BCC4648
CAS No.:72-80-0
- Metandienone
Catalog No.:BCC9025
CAS No.:72-63-9
- b-Casomorphin (1-3)
Catalog No.:BCC1007
CAS No.:72122-59-9
- 2-Hydroxyplatyphyllide
Catalog No.:BCN7119
CAS No.:72145-19-8
- Aflatoxin B2
Catalog No.:BCC9213
CAS No.:7220-81-7
- Calcitetrol
Catalog No.:BCC1446
CAS No.:72203-93-1
- Parsonsine
Catalog No.:BCN2111
CAS No.:72213-98-0
- Echitovenidine
Catalog No.:BCN7482
CAS No.:7222-35-7
- 2-Hydroxyeupatolide
Catalog No.:BCN2490
CAS No.:72229-33-5
- 2alpha-Hydroxyeupatolide 8-O-angelate
Catalog No.:BCN7340
CAS No.:72229-39-1
- Laurifoline
Catalog No.:BCN4278
CAS No.:7224-61-5
- Org 24598 lithium salt
Catalog No.:BCC7845
CAS No.:722456-08-8
- AZD1152
Catalog No.:BCC1393
CAS No.:722543-31-9
- Barasertib (AZD1152-HQPA)
Catalog No.:BCC2168
CAS No.:722544-51-6
Antileishmanial activity of the terpene nerolidol.[Pubmed:15855481]
Antimicrob Agents Chemother. 2005 May;49(5):1679-87.
The activity of Nerolidol, a sesquiterpene used as a food-flavoring agent and currently under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs, was evaluated against Leishmania species. Nerolidol inhibited the growth of Leishmania amazonensis, L. braziliensis, and L. chagasi promastigotes and L. amazonensis amastigotes with in vitro 50% inhibitory concentrations of 85, 74, 75, and 67 microM, respectively. The treatment of L. amazonensis-infected macrophages with 100 microM Nerolidol resulted in 95% reduction in infection rates. Inhibition of isoprenoid biosynthesis, as shown by reduced incorporation of [2-(14)C]mevalonic acid (MVA) or [1-(14)C]acetic acid precursors into dolichol, ergosterol, and ubiquinone, was observed in Nerolidol-treated promastigotes. This drug effect can be attributed to the blockage of an early step in the mevalonate pathway, since incorporation of the precursor [1(n)-(3)H]farnesyl pyrophosphate in polyisoprenoids is not inhibited by Nerolidol. L. amazonensis-infected BALB/c mice were treated with intraperitoneal doses of 100 mg/kg/day for 12 days or topically with 5 or 10% ointments for 4 weeks. Significant reduction of lesion sizes in Nerolidol treated mice was observed for both treatment routes. However, long-term follow up indicated that the disease was not cured in this highly susceptible animal model. Nonetheless, the in vitro activity of Nerolidol against these parasites may prove a useful tool for the development of new drugs for the treatment of leishmaniasis. In addition, biosynthesis of dolichols with 11 and 12 isoprene units was identified in Leishmania, as described for other trypanosomatids and Apicomplexa.
Antifungal effect of eugenol and nerolidol against Microsporum gypseum in a guinea pig model.[Pubmed:17202684]
Biol Pharm Bull. 2007 Jan;30(1):184-8.
Essential oils have been widely used in anti-infectious application. In the present study, we elucidated the antifungal activities of eugenol and Nerolidol isolated from Japanese cypress oil in a guinea pig model infected by Microsporum gypseum (M. gypseum). A minimal inhibitory concentration (MIC), skin lesion scoring, hair culture and histopathologic examination of skin tissues were performed to evaluate the antifungal effect of these oils. The MICs of eugenol, Nerolidol and econazole (positive control) were 0.01-0.03% and 0.5-2% and 4-16 microg/ml, respectively. Based on these MICs, eugenol and Nerolidol were adjusted to 10% concentration with a base of Vaseline petroleum jelly and were applied topically to the skin lesion infected with M. gypseum daily for 3 weeks. Both eugenol and Nerolidol were clinically effective at improving the lesion during the first week of application, as determined by skin lesion scoring. Nerolidol improved the skin lesions infected by M. gypseum, but eugenol did not, as determined in the hair culture test. Histopathologic examination revealed that the eugenol- and Nerolidol-treated groups had a lower degree of hyperkeratosis and inflammatory cell infiltration than the positive control. Taken together, these results suggest that eugenol and Nerolidol could apply supplementary antifungal agents.
Nerolidol, an antiulcer constituent from the essential oil of Baccharis dracunculifolia DC (Asteraceae).[Pubmed:17913068]
Z Naturforsch C. 2007 Jul-Aug;62(7-8):537-42.
In this study, the antiulcerogenic effect of essential oil from Baccharis dracunculifolia was evaluated using the model of acute gastric lesions induced by ethanol. The ulcerative lesion index (ULI) was significantly reduced by oral administration of the essential oil of B. dracunculifolia at doses of 50, 250 and 500 mg/kg which reduced the lesions by 42.79, 45.70 and 61.61%, respectively. The analysis of the chemical composition of the essential oil from B. dracunculifolia by GC showed that this was composed mainly of mono- and sesquiterpenes and the majority compound was Nerolidol. Therefore, antiulcerogenic activity of Nerolidol (50, 250 and 500 mg/kg) was investigated using ethanol-, indomethacin- and stress-induced ulcer models in rat. In the stress-induced ulcer model, a significant reduction of the ULI in animals treated with Nerolidol (50, 250 and 500 mg/kg) and cimetidine (100 mg/kg) was observed, compared to the control group (p < 0.05). The percentage of inhibition of ulcer was 41.22, 51.31, 56.57 and 53.50% in groups treated with 50, 250, 500 mg/kg of Nerolidol and 100 mg/kg of cimetidine (positive control), respectively. Regarding ethanol- and indomethacin-induced ulcer models, it was observed that the treatment with Nerolidol (250 and 500 mg/ kg) significantly reduced the ULI in comparison with the control group (p < 0.05). The dose of 50 mg/kg reduced the parameters analyzed but this was not statistically significant. In the ethanol-induced model percentage of inhibition of ulcer was 34.20, 52.63, 87.63 and 50.87% in groups treated with 50, 250, 500 mg/kg of Nerolidol and 30 mg/kg of omeprazol (positive control), respectively. In indomethacin-ulcer the percentage of inhibition of ulcer was 34.69, 40.80, 51.02 and 46.93% in groups treated with 50, 250, 500 mg/kg of Nerolidol and 100 mg/ kg of cimetidine (positive control), respectively. The results of this study show that Nerolidol displays antiulcer activity, as it significantly inhibited the formation of ulcers induced in different animal models. However, further pharmacological and toxicological investigations, to delineate the mechanism(s) of action and the toxic effects, are required to allow the use of Nerolidol for the treatment of gastric ulcer.
Anti-biofilm, anti-hemolysis, and anti-virulence activities of black pepper, cananga, myrrh oils, and nerolidol against Staphylococcus aureus.[Pubmed:25027570]
Appl Microbiol Biotechnol. 2014 Nov;98(22):9447-57.
The long-term usage of antibiotics has resulted in the evolution of multidrug-resistant bacteria. Unlike antibiotics, anti-virulence approaches target bacterial virulence without affecting cell viability, which may be less prone to develop drug resistance. Staphylococcus aureus is a major human pathogen that produces diverse virulence factors, such as alpha-toxin, which is hemolytic. Also, biofilm formation of S. aureus is one of the mechanisms of its drug resistance. In this study, anti-biofilm screening of 83 essential oils showed that black pepper, cananga, and myrrh oils and their common constituent cis-Nerolidol at 0.01 % markedly inhibited S. aureus biofilm formation. Furthermore, the three essential oils and cis-Nerolidol at below 0.005 % almost abolished the hemolytic activity of S. aureus. Transcriptional analyses showed that black pepper oil down-regulated the expressions of the alpha-toxin gene (hla), the nuclease genes, and the regulatory genes. In addition, black pepper, cananga, and myrrh oils and cis-Nerolidol attenuated S. aureus virulence in the nematode Caenorhabditis elegans. This study is one of the most extensive on anti-virulence screening using diverse essential oils and provides comprehensive data on the subject. This finding implies other beneficial effects of essential oils and suggests that black pepper, cananga, and myrrh oils have potential use as anti-virulence strategies against persistent S. aureus infections.
Inhibition of azoxymethane-induced neoplasia of the large bowel by 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene (nerolidol).[Pubmed:1988176]
Carcinogenesis. 1991 Jan;12(1):151-2.
The inhibitory capacities of four terpenes on azoxymethane (AOM)-induced neoplasia of the large bowel and duodenum was studied in male F344 rats. A complete course of AOM administrations was given and 3 days later the rats were fed a semipurified diet containing 5 mg/g of the test compounds, i.e. 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene (Nerolidol), beta-citronellol, (+/-)-linalool and (1R,2S,5R)-(-)-menthol or a corresponding control diet. The experiment was terminated 22 weeks after the last dose of AOM. Under these conditions, Nerolidol showed an inhibitory effect on carcinogenesis of the large bowel. The number of rats bearing large bowel neoplasms (adenomas) was reduced from 82% in the controls to 33% in rats fed Nerolidol and the number of tumors/rat from 1.5 in the controls to 0.7 in the Nerolidol group. A reduction in adenocarcinomas of the duodenum was found but the data are not statistically significant. The effects of Nerolidol are of interest in terms of the identification of a new inhibitor of carcinogenesis of the large bowel. The chemical structure of Nerolidol suggests the possibility that the compound might have an impact on protein prenylation or some other aspect of the mevalonate pathway, but this remains to be established.
Antioxidant effects of nerolidol in mice hippocampus after open field test.[Pubmed:23765368]
Neurochem Res. 2013 Sep;38(9):1861-70.
The aim of this study was to evaluate the neuroprotective effects of Nerolidol in mice hippocampus against oxidative stress in neuronal cells compared to ascorbic acid (positive control) as well as evaluated the Nerolidol sedative effects by open field test compared to diazepam (positive control). Thirty minutes prior to behavioral observation on open field test, mice were intraperitoneally treated with vehicle, Nerolidol (25, 50 and 75 mg/kg), diazepam (1 mg/kg) or ascorbic acid (250 mg/kg). To clarify the action mechanism of of Nerolidol on oxidative stress in animals subjected to the open field test, Western blot analysis of Mn-superoxide dismutase and catalase in mice hippocampus were performed. In Nerolidol group, there was a significant decrease in lipid peroxidation and nitrite levels when compared to negative control (vehicle). However, a significant increase was observed in superoxide dismutase and catalase activities in this group when compared to the other groups. Vehicle, diazepam, ascorbic acid and Nerolidol groups did not affected Mn-superoxide dismutase, catalase mRNA or protein levels. Our findings strongly support the hypothesis that oxidative stress occurs in hippocampus. Nerolidol showed sedative effects in animals subjected to the open field test. Oxidative process plays a crucial role on neuronal pathological consequence, and implies that antioxidant effects could be achieved using this sesquiterpene.