(-)-Bornyl acetateCAS# 5655-61-8 |
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Quality Control & MSDS
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Chemical structure
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| Cas No. | 5655-61-8 | SDF | Download SDF |
| PubChem ID | 93009 | Appearance | Colorless liquid |
| Formula | C12H20O2 | M.Wt | 196.28 |
| Type of Compound | Monoterpenoids | Storage | Desiccate at -20°C |
| Synonyms | L-Bornyl acetate;76-49-3 | ||
| Solubility | Soluble in ethanol; insoluble in water | ||
| Chemical Name | [(1S,3R,4S)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate | ||
| SMILES | CC(=O)OC1CC2CCC1(C2(C)C)C | ||
| Standard InChIKey | KGEKLUUHTZCSIP-HOSYDEDBSA-N | ||
| Standard InChI | InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12+/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. |
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| 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. |
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| 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 | Bornyl acetate shows highly active whitening and antioxidant activities, has potential applications in cosmeceutical materials. Bornyl acetate has anti-inflammatory activity, may be developed as a preventive agent for lung inflammatory diseases and osteoarthritis; it also has an antiabortive effect through modulation of immunological balance at maternal-fetal interface. |
| Targets | p38MAPK | NF-kB | JNK | IL Receptor | MMP(e.g.TIMP) | AP-1 | SOD | IFN-γ |
| In vitro | Inhibition of lung inflammatory responses by bornyl acetate is correlated with regulation of myeloperoxidase activity.[Pubmed: 24120240]J Surg Res. 2014 Jan;186(1):436-45.Bornyl acetate is a bicyclic monoterpene present in numerous conifer oils. In this study, we aimed at clarifying the potential anti-inflammatory function and mechanism of Bornyl acetate by using lipopolysaccharide (LPS)-induced acute lung injury murine model and RAW 264.7 cells.
Whitening and antioxidant activities of bornyl acetate and nezukol fractionated from Cryptomeria japonica essential oil.[Pubmed: 23714012 ]Int J Cosmet Sci. 2013 Oct;35(5):484-90.The aim of this study was to investigate the whitening and antioxidant activities of essential oils from Cryptomeria japonica by determining their tyrosinase inhibition, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and superoxide dismutase (SOD)-like activities.
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| Kinase Assay | Bornyl acetate has an anti-inflammatory effect in human chondrocytes via induction of IL-11.[Pubmed: 25545915 ]IUBMB Life. 2014 Dec;66(12):854-9.Both pro-inflammatory cytokines and anti-inflammatory cytokines generated by chondrocytes play essential roles in the process of Rheumatoid arthritis and osteoarthritis (OA). Bornyl acetate is the main volatile constituent in numerous conifer oils and some Chinese traditional herbs, which has displayed an anti-inflammatory effect before. |
| Animal Research | Quercetin and Bornyl Acetate Regulate T-Lymphocyte Subsets and INF-γ/IL-4 Ratio In Utero in Pregnant Mice.[Pubmed: 20981318]Evid Based Complement Alternat Med. 2011;2011:745262.The objective of this study is to investigate the antiabortive effects of Quercetin and Bornvl Acetate and their immunological modulation at maternal-fetal interface. |
(-)-Bornyl acetate Dilution Calculator
(-)-Bornyl acetate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.0948 mL | 25.4738 mL | 50.9476 mL | 101.8953 mL | 127.3691 mL |
| 5 mM | 1.019 mL | 5.0948 mL | 10.1895 mL | 20.3791 mL | 25.4738 mL |
| 10 mM | 0.5095 mL | 2.5474 mL | 5.0948 mL | 10.1895 mL | 12.7369 mL |
| 50 mM | 0.1019 mL | 0.5095 mL | 1.019 mL | 2.0379 mL | 2.5474 mL |
| 100 mM | 0.0509 mL | 0.2547 mL | 0.5095 mL | 1.019 mL | 1.2737 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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Whitening and antioxidant activities of bornyl acetate and nezukol fractionated from Cryptomeria japonica essential oil.[Pubmed:23714012]
Int J Cosmet Sci. 2013 Oct;35(5):484-90.
OBJECTIVES: The aim of this study was to investigate the whitening and antioxidant activities of essential oils from Cryptomeria japonica by determining their tyrosinase inhibition, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and superoxide dismutase (SOD)-like activities. METHODS: Essential oils of C. japonica leaves were extracted with distilled water, and after condensation of volatile constituents, the condensates were extracted with ethyl acetate. Crude essential oils of C. japonica were divided into six fractions by thin layer chromatography and open column chromatography, and their chemical analysis was performed by GC/MS. Major compounds of fractions were composed of kaurene, bornyl acetate, nezukol, (-)-4-terpineol, delta-cadinene, alpha-terpineol, gamma-eudesmol, alpha-eudesmol and elemol. RESULTS: For tyrosinase inhibitory activity using two substrates, l-tyrosine and 3,4-dihydroxyphenylalanine (l-DOPA), kaurene, bornyl acetate and nezukol were highly effective. In antioxidant activity, (-)-4-terpinenol and delta-cadinene showed high DPPH radical scavenging activity, and bornyl acetate and nezukol indicated extremely high SOD-like activity. CONCLUSION: Therefore, bornyl acetate and nezukol fractionated from C. japonica essential oil, which showed highly active whitening and antioxidant activities, have potential applications in cosmeceutical materials.
Bornyl acetate suppresses ox-LDL-induced attachment of THP-1 monocytes to endothelial cells.[Pubmed:29655164]
Biomed Pharmacother. 2018 Jul;103:234-239.
Leukocyte recruitment to the surface of the endothelium plays a pivotal role in the development of cardiovascular diseases. Bornyl acetate is the main volatile constituent present in numerous conifer oils, which has displayed its anti-oxidant and anti-inflammatory properties in different types of tissues and cells. However, little information regarding the effects of bornyl acetate on vascular endothelial inflammation has been reported before. In the current study, we aimed to investigate the pharmacological roles of bornyl acetate against ox-LDL-induced leukocyte adhesion to the endothelium. Our findings indicate that bornyl acetate ameliorated ox-LDL-induced reduction in cell viability of HUVECs. Additionally, bornyl acetate inhibited the attachment of THP-1 monocytes to HUVECs induced by treatment with ox-LDL through ameliorating the expression of ICAM-1, VCAM-1, and E-selectin. Mechanistically, we found that bornyl acetate could suppress activation of the IkappaBalpha/NF-kappaB signaling pathway. Lastly, our results indicate that bornyl acetate mitigated expression of the pro-inflammatory cytokines TNF-alpha and IL-1beta. Our results suggest the therapeutic potential of bornyl acetate in patients with atherosclerosis.
Bornyl acetate has an anti-inflammatory effect in human chondrocytes via induction of IL-11.[Pubmed:25545915]
IUBMB Life. 2014 Dec;66(12):854-9.
Both pro-inflammatory cytokines and anti-inflammatory cytokines generated by chondrocytes play essential roles in the process of Rheumatoid arthritis and osteoarthritis (OA). Bornyl acetate is the main volatile constituent in numerous conifer oils and some Chinese traditional herbs, which has displayed an anti-inflammatory effect before. In this study, we found that bornyl acetate elevates the expression of IL-11 at both the mRNA and protein levels. Interestingly, our results indicated that IL-1beta-mediated up-regulation of IL-6, IL-8, MMP-1, and MMP-13 was significantly compromised by IL-11 co-treatment on mRNA levels and protein levels. The antagonistic effects of bornyl acetate on IL-1beta induced targets MMP-1 and MMP-13 were diminished by IL-11 knockdown. Mechanistically, our results indicated that bornyl acetate significantly elevates the expression of AP-1 component c-fos, which may influence gross AP-1 activity and initial the transcription of IL-11. Indeed, expression of IL-11 was reversed upon c-fos knockdown. Our results suggest the therapeutic potentials of bornyl acetate in patients with OA.
Thymus mastichina L. essential oils from Murcia (Spain): Composition and antioxidant, antienzymatic and antimicrobial bioactivities.[Pubmed:29304179]
PLoS One. 2018 Jan 5;13(1):e0190790.
The compositions of essential oils (EOs) from Spanish marjoram (Thymus mastichina L.) grown in several bioclimatic zones of Murcia (SE Spain) were studied to determine their absolute and relative concentrations using gas chromatography-mass spectrometry. 1,8-Cineole and linalool were the main components, followed by alpha-pinene, beta-pinene and alpha-terpineol. (-)-Linalool, (+)-alpha-terpineol and (+)-alpha-pinene were the most abundant enantiomers. When the antioxidant capacities of T. mastichina EOs and their compounds were measured by five methods, EOs and linalool, linalyl acetate, alpha-terpinene and gamma-terpinene, among others, showed antioxidant activities. All four T. mastichina EOs inhibited both lipoxygenase and acetylcholinesterase activities, and they might be useful for further research into inflammatory and Alzheimer diseases. Bornyl acetate and limonene showed the highest lipoxygenase inhibition and 1,8-cineole was the best acetylcholinesterase inhibitor. Moreover, these EOs inhibited the growth of Escherichia coli, Staphylococcus aureus and Candida albicans due to the contribution of their individual compounds. The results underline the potential use of these EOs in manufactured products, such as foodstuff, cosmetics and pharmaceuticals.
Quercetin and Bornyl Acetate Regulate T-Lymphocyte Subsets and INF-gamma/IL-4 Ratio In Utero in Pregnant Mice.[Pubmed:20981318]
Evid Based Complement Alternat Med. 2011;2011:745262.
The objective of this study is to investigate the antiabortive effects of Quercetin and Bornvl Acetate and their immunological modulation at maternal-fetal interface. Lipopolysaccharide (LPS) was injected via tail vein to induce abortion in mice which received Quercetin and Bornvl Acetate at days 4-7 of gestation. Uterine CD4+/CD8+ T lymphocytes and IFN-gamma/IL-4 of each group (n = 10) were detected by immunohistochemistry and enzyme-linked immunosorbent assay, respectively. The ratio of CD4+/CD8+ increased significantly (P < .01) in the uterus of LPS-induced abortion mice. In the Quercetin and Bornvl Acetate pretreated mice followed by LPS administration, the ratio of CD4+/CD8+ dropped to 0.562 +/- 0.021, lower than that of LPS-abortion group (P < .01). The mean value of IFN-gamma/IL-4 in LPS-treated mice was 0.310 +/- 0.066, higher than that of Quercetin and Bornyl Acetate group. The results indicate that Quercetin and Bornyl Acetate have an antiabortive effect through modulation of immunological balance at maternal-fetal interface.
Inhibition of lung inflammatory responses by bornyl acetate is correlated with regulation of myeloperoxidase activity.[Pubmed:24120240]
J Surg Res. 2014 Jan;186(1):436-45.
BACKGROUND: Bornyl acetate is a bicyclic monoterpene present in numerous conifer oils. In this study, we aimed at clarifying the potential anti-inflammatory function and mechanism of bornyl acetate by using lipopolysaccharide (LPS)-induced acute lung injury murine model and RAW 264.7 cells. MATERIALS AND METHODS: RAW 264.7 cells were pretreated with bornyl acetate 1 h before LPS stimulation and cell-free super supernatants were collected to measure cytokine concentrations. To induce acute lung injury, BALB/c mice were injected intranasally with LPS and treated with bornyl acetate 1 h before LPS stimulation. Seven hours after administration, the bronchoalveolar lavage fluid (BALF) was collected for measuring the cell count and cytokine production. We collected lungs for assaying wet-to-dry weight ratio, myeloperoxidase activity, and histologic changes. The extent of phosphorylation of mitogen-activated protein kinases and nuclear factor kappaB was detected by Western blot. RESULTS: Our results showed that bornyl acetate downregulated the levels of proinflammatory cytokines in vitro and in vivo; reduced the number of total cells, neutrophils, and macrophages in BALF; attenuated the histologic alterations in the lung; decreased the wet-to-dry weight ratio in BALF; and suppressed NF-kappa-B inhibitor alpha, extracellular regulated protein kinases, c-JunN-terminal kinase, p38 mitogen-activated protein kinase activation. CONCLUSIONS: These findings suggested that bornyl acetate may be developed as a preventive agent for lung inflammatory diseases.
