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Zingiberene

CAS# 495-60-3

Zingiberene

2D Structure

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Zingiberene

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Chemical Properties of Zingiberene

Cas No. 495-60-3 SDF Download SDF
PubChem ID 92776.0 Appearance Powder
Formula C15H24 M.Wt 204.36
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
SMILES CC1=CCC(C=C1)C(C)CCC=C(C)C
Standard InChIKey KKOXKGNSUHTUBV-LSDHHAIUSA-N
Standard InChI InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m0/s1
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.

Source of Zingiberene

Zingiber officinale Rosc.

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Preparing Stock Solutions of Zingiberene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.8933 mL 24.4666 mL 48.9333 mL 97.8665 mL 122.3331 mL
5 mM 0.9787 mL 4.8933 mL 9.7867 mL 19.5733 mL 24.4666 mL
10 mM 0.4893 mL 2.4467 mL 4.8933 mL 9.7867 mL 12.2333 mL
50 mM 0.0979 mL 0.4893 mL 0.9787 mL 1.9573 mL 2.4467 mL
100 mM 0.0489 mL 0.2447 mL 0.4893 mL 0.9787 mL 1.2233 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.

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References on Zingiberene

Efficacy of essential oil from ginger (Zingiber officinale) for anesthesia and transport sedation of pacu (Piaractus mesopotamicus).[Pubmed:38630162]

Fish Physiol Biochem. 2024 Apr 17.

This study evaluated the anesthetic and sedative effects of the essential oil of Zingiber officinale (EOZO) on juvenile pacu (Piaractus mesopotamicus). Experiment 1 evaluated concentrations of 0, 50, 100, 200 and 400 mg L(-1) EOZO for times of induction and recovery from anesthesia. Furthermore, hematological responses and residual components of EOZO in plasma were determined immediately after anesthesia. Experiment 2 evaluated the effect of 0, 10, 20 and 30 mg L(-1) EOZO on water quality, blood variables and residual components of EOZO in plasma and tissues (muscle and liver) immediately after 2 h of transport. Survival was 100%. The three main compounds of EOZO [Zingiberene (32.27%), beta-sesquiphellandrene (18.42%) and beta-bisabolene (13.93%)] were observed in animal plasma and tissues (muscle and liver) after anesthesia and transport, demonstrating a direct linear effect among the evaluated concentrations. The concentration of 200 mg L(-1) EOZO promoted surgical anesthesia of pacu and prevented an increase in monocyte and neutrophil levels, yet did not alter other hematological parameters. The use of 30 mg L(-1) EOZO has a sedative effect on juvenile pacu, thereby reducing oxygen consumption during transport. Furthermore, the use of 30 mg L(-1) EOZO in transport water prevented an increase in hemoglobin and hematocrit, with minimal influences on other blood variables.

Aviation Mutagenesis Alters the Content of Volatile Compounds in Dahongpao (Camellia sinensis) Leaves and Improves Tea Quality.[Pubmed:38540936]

Foods. 2024 Mar 20;13(6):946.

Aviation mutagenesis is a fast and efficient breeding method. In this study, we analyzed the effect of aviation mutagenesis on volatile compounds and odor characteristics in Dahongpao fresh leaves and gross tea for the first time. The results showed that aviation mutagenesis significantly increased the total volatile compounds of Dahongpao fresh leaves and gross tea. Aviation mutagenesis most critically significantly increased the content of beta-myrcene in Dahongpao fresh leaves, prompting its conversion to beta-pinene, cubebol, beta-phellandrene, Zingiberene, (Z,Z)-3,6-nonadienal, and 6-pentyloxan-2-one after processing, which in turn enhanced the fruity, green, spicy, and woody odor characteristics of the gross tea. This study provided a reference for further exploration of aviation mutagenic breeding of Camellia sinensis.

Computational investigation of turmeric phytochemicals targeting PTR1 enzyme of Leishmania species.[Pubmed:38533011]

Heliyon. 2024 Mar 16;10(6):e27907.

In this study, we used in silico techniques to identify available parasite treatments, representing a promising therapeutic avenue. Building upon our computational initiatives aimed at discovering natural inhibitors for various target enzymes from parasites causing neglected tropical diseases (NTDs), we present novel findings on three turmeric-derived phytochemicals as inhibitors of Leishmania pteridine reductase I (PTR1) through in silico methodologies. PTR1, a crucial enzyme in the unique folate metabolism of trypanosomatid parasites, holds established therapeutic significance. Employing MOE software, a molecular docking analysis assesses the efficacy of turmeric phytochemicals against Leishmania PTR1. Validation of the docking protocol is confirmed with an RMSD value of 2. Post-docking, compounds displaying notable interactions with critical residues and binding affinities ranging between -6 and -8 kcal/mol are selected for interaction pattern exploration. Testing twelve turmeric phytochemicals, including curcumin, Zingiberene, curcumol, curcumenol, eugenol, bisdemethoxycurcumin, tetrahydrocurcumin, tryethylcurcumin, turmerones, turmerin, demethoxycurcumin, and turmeronols, revealed binding affinities ranging from -5.5 to -8 kcal/mol. Notably, curcumin, demethoxycurcumin, and bisdemethoxycurcumin exhibit binding affinities within -6.5 to -8 kcal/mol and establish substantial interactions with catalytic residues. These phytochemicals hold promise as lead structures for rational drug design targeting Leishmania spp. PTR in future applications. This work underscores the potential of these identified phytochemicals in the development of more effective inhibitors, demonstrating their relevance in addressing neglected tropical diseases caused by parasites.

Quantifying terpenes in tomato leaf extracts from different species using gas chromatography-mass spectrometry (GC-MS).[Pubmed:38453049]

Anal Biochem. 2024 Jun;689:115503.

Terpenes play a vital role in plant defense; tomato plants produce a diverse range of terpenes within specialized glandular trichomes, influencing interactions with herbivores, predators, and pollinators. This study employed two distinct methods, namely leaf dip and maceration, to extract trichomes from tomato leaves. Terpene quantification was carried out using Gas Chromatography-Mass Spectrometry (GC-MS). The leaf dip method proved effective in selectively targeting trichome content, revealing unique extraction patterns compared to maceration. The GC-MS method demonstrated high linearity, accuracy, sensitivity, and low limits of detection and quantification. Application of the method to different tomato species (Solanum pennellii, Solanum pimpinellifolium, Solanum galapagense, Solanum habrochaites, and Solanum lycopersicum) identified significant variation in terpene content among these species, highlighting the potential of specific accessions for breeding programs. Notably, the terpene alpha-Zingiberene, known for its repellency against whiteflies, was found in high quantities (211.90-9155.13 mug g(-1)) in Solanum habrochaites accession PI209978. These findings provide valuable insights into terpenoid diversity for plant defense mechanisms, guiding future research on developing pest-resistant tomato cultivars. Additionally, the study underscores the broader applications of terpenes in agriculture.

Extraction of High Value Products from Zingiber officinale Roscoe (Ginger) and Utilization of Residual Biomass.[Pubmed:38398623]

Molecules. 2024 Feb 16;29(4):871.

Zingiber officinale Roscoe (ginger) is a plant from the Zingiberaceae family, and its extracts have been found to contain several compounds with beneficial bioactivities. Nowadays, the use of environmentally friendly and sustainable extraction methods has attracted considerable interest. The main objective of this study was to evaluate subcritical propane (scPropane), supercritical CO(2) (scCO(2)), and supercritical CO(2) with ethanol (scCO(2) + EtOH) as co-solvent methods for the extraction of high value products from ginger. In addition, the reuse/recycling of the secondary biomass in a second extraction as a part of the circular economy was evaluated. Both the primary and the secondary biomass led to high yield percentages, ranging from 1.23% to 6.42%. The highest yield was observed in the scCO(2) + EtOH, with biomass prior used to scCO(2) extraction. All extracts presented with high similarities as far as their total phenolic contents, antioxidant capacity, and chemical composition. The most abundant compounds, identified by the two different gas chromatography-mass spectrometry (GC-MS) systems present, were a-Zingiberene, beta- sesquiphellandrene, a-farnesene, beta-bisabolene, zingerone, gingerol, a-curcumene, and gamma-muurolene. Interestingly, the reuse/recycling of the secondary biomass was found to be promising, as the extracts showed high antioxidant capacity and consisted of significant amounts of compounds with beneficial properties.

Optimum drying conditions for ginger (Zingiber officinale Roscoe) based on time, energy consumption and physicochemical quality.[Pubmed:38144724]

Food Chem X. 2023 Nov 10;20:100987.

The effect of ultrasonic pre-treatment on moisture removal characteristics of ginger in a convective dryer was investigated. The slabs were dried by practicing sonication durations of 0, 15 and 30 min at different levels of the air temperature and velocity. Following increasing the sonication duration and air temperature, required time and energy to dehydrate the samples were decreased. The pre-treatment played important role in improving rehydration capability and surface color retention in the dried gingers. Content of the main volatile component (alpha-Zingiberene) was not influenced by the sonication. Mean values for the phenolic contents and antioxidant activity at sonication duration of 0, 15 and 30 min were determined to be 18.93, 18.15 and 17.49 GAE/g dry matter and 83.57, 78.33 and 74.58 %, respectively. The desired values for the temperature, velocity and sonication duration were revealed to be about 66 degrees C, 3 m/s and 20 min, respectively.

Chromatographic analysis of the chemical composition and anticancer activities of Curcuma longa extract cultivated in Palestine.[Pubmed:38027225]

Open Life Sci. 2023 Nov 23;18(1):20220767.

Curcuma longa (turmeric) is a plant that has been extensively utilized in traditional medicine for centuries. Turmeric has a long history of use in both food and traditional medicine for the treatment of ailments such as diarrhea, cancer, flatulence, and dyspepsia. In Palestine, this plant was cultivated for the first time. The objective of this study was to characterize the extract of C. longa and assess its antimutagenic activity against a variety of cancer cells. Gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC) methods were employed to identify the constituents of turmeric. The cytotoxic effects of C. longa were evaluated on cancer and normal cell lines using the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium assay. The results revealed the presence of 10 components in turmeric extract as identified by GC-MS. The major constituents comprising 78% of the total constituents were alpha-Zingiberene (27.51%), tumeron (19.44%), beta-sesquiphellandrene (19.40%), and aromatic-tumeron (11.63%). HPLC analysis successfully separated the main constituent, curcumin (1.78%), along with two other curcumin derivatives. The cytotoxicity results demonstrated potent anticancer activity of the C. longa extract against HeLa and LX2 cell lines, with IC(50) values of 46.84 +/- 2.12 and 29.77 +/- 1 microg/mL, respectively. Furthermore, the plant extract at a concentration of 250 microg/mL exhibited over 95% inhibition against all tested cancer cell lines. These findings highlight the promising potential of turmeric as a natural source with powerful anticancer activities. Moreover, the extract may possess other biological activities such as antioxidant and antimicrobial properties, which could be explored in future studies.

Starch extraction from avocado by-product and its use for encapsulation of ginger essential oil by electrospinning.[Pubmed:37879583]

Int J Biol Macromol. 2024 Jan;254(Pt 1):127617.

Starches from alternative sources, such as avocado seed, have potential for application in the encapsulation of essential oils. This study aimed to extract starch from avocado seeds and its use as wall material to encapsulate ginger essential oil (GEO), at different concentrations. The fibers were produced by electrospinning and evaluated by morphology, size, infrared spectra, thermogravimetric properties, contact angle, loading capacity, and antibacterial activity. The major compounds in GEO were alpha-Zingiberene, beta-sesquiphellandrene, alpha-farnesene, and alpha-curcumene. The starch-GEO fibers presented a higher diameter ( approximately 553 nm) than those without GEO (345 nm). Encapsulation of GEO in starch fibers increased their thermal degradation temperatures from 165.8 degrees C (free GEO) to 257.6 degrees C (40 % GEO fibers). The starch-GEO fibers presented characteristic bands of their constituents by infrared spectra. Loading capacity ranged from 44 to 54 %. The fibers showed hydrophilic character, with a contact angle of <90 degrees . Free GEO and the fibers with 50 % of GEO displayed antibacterial activity against Escherichia coli, proving the bioactivity of the starch-GEO fibers and its possible applicability for food packaging. Avocado seed starch showed to be a great wall material for GEO encapsulation.

A comparative study on essential oils from the leaves and stems of Vietnamese Mikania micrantha Kunth.[Pubmed:37635675]

Nat Prod Res. 2023 Aug 28:1-7.

Mikania micrantha Kunth is widely known as potential herbal medicine, although it is an invasive alien species in Southeast Asia. In this study, the essential oils from leaves and stems of M. micrantha were extracted by hydrodistillation method, and the chemical profiles of essential oils were then analysed by gas chromatography (GC) and gas chromatography coupled with mass spectrometry (GC/MS). It was found that there were similarities and differences in chemical compositions and their percentage between the essential oils obtained from these two parts. The dominant components of leaves essential oil are beta-Cubebene, Germacrene D, and alpha-Zingiberene, accounting for 11.34%, 10.96%, and 10.76%, respectively. Additionally, the major components of stems essential oils are D-Limonene (16.99%), beta-Pinene (7.91%), and alpha-Zingiberene (7.26%). The research sheds fresh light on the chemical makeup of M. micrantha essential oils, emphasising their potential for the future.

Anticholinesterases activity of Murraya koenigii (L.) Spreng. and Murraya paniculata (L.) Jacq. essential oils with GC/MS analysis and molecular docking.[Pubmed:37516925]

Nat Prod Res. 2023 Jul 30:1-5.

GC/MS analysis of Murraya koenigii (L.) Spreng. and Murraya paniculata (L.) Jacq. leaves revealed the identification of 73 components, with an evident greater contribution of monoterpenes hydrocarbons to their total volatiles. alpha-Pinene (37.5%) and beta-caryophyllene (27.4%) were the most abundant compounds in M. koenigii leaves and beta-phellandrene (40.7%) in M. paniculata leaves, using headspace. beta-Phellandrene (33.7%) was the major constituent by M. koenigii leaves where germacrene D (23.8%), and delta-elemene (22.0%) were predominant in M. paniculata leaves, using steam distillation. M. koenigii leaves oil showed quite remarkable cholinesterase inhibitory activity, where oil of M. paniculata leaves showed strong inhibitory activity against AChE (IC(50)=13.2 +/- 0.9 microg/mL) and BChE (IC(50)=5.1 +/- 0.3 microg/mL). Germacrene D, alpha-Zingiberene, and delta-elemene showed higher affinity to BChE than AChE as revealed from docking scores (S = -5.65 to -6.03 Kcal/mol) for BChE and (S = -5.56 to -6.25 Kcal/mol) for AChE.

Chemical Variability of Essential Oils from Corsican Hops and Highlighting Their Influence on Hops' Aroma.[Pubmed:37444357]

Foods. 2023 Jul 6;12(13):2613.

Essential oils from wild Corsican hops have never been described before. Following selective harvesting and extraction of plant material, chemical analysis was performed by GC-FID and GC-MS. Subsequent quantitative analysis demonstrated significant inter-stations variability due to pedoclimatic conditions. These singularities produce organoleptic differences, especially within Italian hops, which are the current benchmark for the Mediterranean hops' population. Corsican wild hops are no exception. Accordingly, three olfactive bouquets were identified by a panel of selected and trained sensory analysts: woody herbaceous ginger notes, herbaceous citrus notes, and common notes. These bouquets appeared to be correlated to pedoclimatic parameters mentioned earlier such as altitude and proximity to the sea. A very rare and appreciated bouquet was associated with high levels of Zingiberene in hops growing at moderate altitude and relatively far from the coastline. This study shows the importance of growing sites and pedoclimatic conditions to produce hops with the desired organoleptic notes during the beer making process and provides detailed identification of essential oils from Corsican wild hops.

Casearia Essential Oil: An Updated Review on the Chemistry and Pharmacological Activities.[Pubmed:37410861]

Chem Biodivers. 2023 Sep;20(9):e202300492.

Casearia species are found in the America, Africa, Asia, and Australia and present pharmacological activities, besides their traditional uses. Here, we reviewed the chemical composition, content, pharmacological activities, and toxicity of the essential oils (EOs) from Casearia species. The EO physical parameters and leaf botanical characteristics were also described. The bioactivities of the EOs from the leaves and their components include cytotoxicity, anti-inflammatory, antiulcer, antimicrobial, antidiabetic, antioxidant, antifungal, and antiviral activities. The main components associated with these activities are the alpha-Zingiberene, (E)-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, alpha-humulene, beta-acoradiene, and delta-cadinene. Data on the toxicity of these EOs are scarce in the literature. Casearia sylvestris Sw. is the most studied species, presenting more significant pharmacological potential. The chemical variability of EOs components was also investigated for this species. Caseria EOs have relevant pharmacological potential and must be further investigated and exploited.

Antioxidant Activity in Extracts from Zingiberaceae Family: Cardamom, Turmeric, and Ginger.[Pubmed:37241765]

Molecules. 2023 May 11;28(10):4024.

An increase in life expectancy leads to a greater impact of chronic non-communicable diseases. This is even more remarkable in elder populations, to whom these become main determinants of health status, affecting mental and physical health, quality of life, and autonomy. Disease appearance is closely related to the levels of cellular oxidation, pointing out the importance of including foods in one's diet that can prevent oxidative stress. Previous studies and clinical data suggest that some plant-based products can slow and reduce the cellular degradation associated with aging and age-related diseases. Many plants from one family present several applications that range from the food to the pharmaceutical industry due to their characteristic flavor and scents. The Zingiberaceae family, which includes cardamom, turmeric, and ginger, has bioactive compounds with antioxidant activities. They also have anti-inflammatory, antimicrobial, anticancer, and antiemetic activities and properties that help prevent cardiovascular and neurodegenerative diseases. These products are abundant sources of chemical substances, such as alkaloids, carbohydrates, proteins, phenolic acids, flavonoids, and diarylheptanoids. The main bioactive compounds found in this family (cardamom, turmeric, and ginger) are 1,8-cineole, alpha-terpinyl acetate, beta-turmerone, and alpha-Zingiberene. The present review gathers evidence surrounding the effects of dietary intake of extracts of the Zingiberaceae family and their underlying mechanisms of action. These extracts could be an adjuvant treatment for oxidative-stress-related pathologies. However, the bioavailability of these compounds needs to be optimized, and further research is needed to determine appropriate concentrations and their antioxidant effects in the body.

Antibacterial, bacteriolytic, and antibiofilm activities of the essential oil of temu giring (Curcuma heyneana Val.) against foodborne pathogens.[Pubmed:37218156]

Food Sci Technol Int. 2023 May 22:10820132231178060.

Foodborne pathogens may cause foodborne illness, which is among the major health problems worldwide. Since the therapeutic options for the treatment of the disease are becoming limited as a result of antibacterial resistance, there is an increasing interest to search for new alternatives of antibacterial. Bioactive essential oils from Curcuma sp become potential sources of novel antibacterial substances. The antibacterial activity of Curcuma heyneana essential oil (CHEO) was evaluated against Escherichia coli, Salmonella typhi, Shigella sonnei, and Bacillus cereus. The principal constituents of CHEO are ar-turmerone, beta-turmerone, alpha-Zingiberene, alpha-terpinolene, 1,8-cineole, and camphor. CHEO exhibited the strongest antibacterial activity against E. coli with a MIC of 3.9 microg/mL, which is comparable to that of tetracycline. The combination of CHEO (0.97 microg/mL) and tetracycline (0.48 microg/mL) produced a synergistic effect with a FICI of 0.37. Time-kill assay confirmed that CHEO enhanced the activity of tetracycline. The mixture disrupted membrane permeability of E. coli and induced cell death. CHEO at MIC of 3.9 and 6.8 microg/mL significantly reduced the formation of biofilm in E. coli. The findings suggest that CHEO has the potential to be an alternative source of antibacterial agents against foodborne pathogens, particularly E. coli.

Essential Oil of Zingiber cassumunar Roxb. and Zingiber officinale Rosc.: A Comparative Study on Chemical Constituents, Antibacterial Activity, Biofilm Formation, and Inhibition of Pseudomonas aeruginosa Quorum Sensing System.[Pubmed:37202876]

Chem Biodivers. 2023 Jun;20(6):e202201205.

Pseudomonas aeruginosa can regulate its pathogenicity via quorum sensing (QS) system. Zingiber cassumunar and Z. officinale have been used for the treatment of infectious diseases. The study aimed to evaluate and compare the chemical constituents, antibacterial, and QS inhibitor of Z. cassumunar essential oils (ZCEO) and Z. officinale essential oils (ZOEO). The chemical constituent was analysed using GC/MS. Broth microdilution and spectrophotometry analysis were used to evaluate their antibacterial and QS inhibitor activities. The main constituent of ZOEO with percent composition above 6 % (alpha-curcumene, alpha-Zingiberene, beta-sesquiphellandrene, and beta-bisabolene, alpha-citral, and alpha-farnesene) were exist in a very minimal percentage less than 0.7 % in Z. cassumunar. All major components of ZCEO with percentages higher than 5 % (terpinen-4-ol, sabinene, gamma-terpinene) were present in low proportion (<1.18 %) in Z. officinale. ZCEO demonstrated moderate antibacterial activity against P. aeruginosa. The combination of ZCEO and tetracycline showed a synergistic effect (FICI of 0.5). ZCEO exhibited strong activity in inhibiting biofilm formation. ZCEO at 1/2 MIC (62.5 mug/mL) was able to reduce pyoverdine, pyocyanin, and proteolytic activity. This is the first report on the activity of ZCEO in the inhibition of P. aeruginosa QS system and it may be used to control the pathogenicity of P. aeruginosa.

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