Bornyl acetate
(Synonyms: (-)-乙酸龙脑酯; L-(-)-Bornyl acetate) 目录号 : GC33501
An acetate form of borneol
Cas No.:76-49-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(±)-Bornyl acetate is a racemic mixture of the acetate form of the monoterpene alcohol borneol that has been found in P. silvestris.1,2 (±)-Bornyl acetate induces an electroantennogram (EAG) response in isolated P. americana (American cockroach) antennae from both male and female cockroaches that is similar to the response induced by sex pheromones.3 It also induces hydrogen peroxide production and apoptosis in M. polymorpha plant cells.4
1.Bardyshev, I.I., and Pertsovskii, A.L.Chemical composition of oxygen-containing gum turpentine fractions from Pinus silvestrisDokl. Akad. Nauk BSSR13(7)617-620(1969) 2.Oritani, T., and Yamashita, K.Microbial resolution of (±)-borneolstAgr. BioI. Chem.38(10)1961-1964(1974) 3.Washio, H., and Nishino, C.Electroantennogram responses to the sex pheromone and other odours in the American cockroachJ. Insect Physiol.22(5)735-741(1976) 4.Izumi, S., Nishio, Y., Takashima, O., et al.Monoterpenoids, potent inducers of apoptosis in the cells of Marchantia polymorphaChem. Lett.26(8)837-838(1997)
| Cas No. | 76-49-3 | SDF | |
| 别名 | (-)-乙酸龙脑酯; L-(-)-Bornyl acetate | ||
| Canonical SMILES | CC1(C)[C@@]2(C)[C@H](OC(C)=O)C[C@]1([H])CC2 | ||
| 分子式 | C12H20O2 | 分子量 | 196.29 |
| 溶解度 | DMSO : ≥ 83.33 mg/mL (424.52 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.0945 mL | 25.4725 mL | 50.945 mL |
| 5 mM | 1.0189 mL | 5.0945 mL | 10.189 mL |
| 10 mM | 0.5095 mL | 2.5473 mL | 5.0945 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Bornyl acetate suppresses ox-LDL-induced attachment of THP-1 monocytes to endothelial cells
Biomed Pharmacother 2018 Jul;103:234-239.PMID:29655164DOI:10.1016/j.biopha.2018.03.152.
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 IκBα/NF-κB signaling pathway. Lastly, our results indicate that Bornyl acetate mitigated expression of the pro-inflammatory cytokines TNF-α and IL-1β. Our results suggest the therapeutic potential of Bornyl acetate in patients with atherosclerosis.
Bornyl acetate: A promising agent in phytomedicine for inflammation and immune modulation
Phytomedicine 2023 Mar 22;114:154781.PMID:37028250DOI:10.1016/j.phymed.2023.154781.
Background: Bornyl acetate (BA), as a bicyclic monoterpene, is an active volatile component widely found in plants across the globe. BA can be used as essence and food flavor agent and is widely used in perfumes and food additives. It remains a key component in several proprietary Chinese medicines. Purpose: This review summarized the pharmacological activity and research prospects of BA, making it the first of its kind to do so. Our aim is to provide a valuable resource for those pursuing research on BA. Methods: Databases including PubMed, Web of Science, and CNKI were used based on search formula "(Bornyl acetate) NOT (review)" from 1967 to 2022. For the relevant knowledge of TCM, we quoted Chinese literature. Articles related to agriculture, industry, and economics were excluded. Results: BA showed rich pharmacological activities: It inhibits the NF-κB signal pathway via affecting the phosphorylation of IKB and the production of IKKs, inhibits the MAPK signal pathway via inhibiting the phosphorylation of ERK, JNK, and p38, down-regulates pro-inflammatory cytokines such as TNF-α, IL-1β, IL-6, up-regulates IL-11, reduces NO production, regulates immune response via up-regulating CD86+, decreases catecholamine secretion, and reduces tau protein phosphorylation. In addition to the pharmacological activities of BA, its toxicity and pharmacokinetics were also discussed in this paper. Conclusion: BA has promising pharmacological properties, especially anti-inflammatory and immunomodulatory effects. It also has sedative properties and potential for use in aromatherapy. Compared to traditional NSAIDs, it has a more favorable safety profile while maintaining efficacy. BA has potential for developing novel drugs for treating various conditions.
Bornyl acetate has an anti-inflammatory effect in human chondrocytes via induction of IL-11
IUBMB Life 2014 Dec;66(12):854-9.PMID:25545915DOI:10.1002/iub.1338.
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-1β-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-1β 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.
Genome-Wide Identification of BAHD Superfamily and Functional Characterization of Bornyl Acetyltransferases Involved in the Bornyl acetate Biosynthesis in Wurfbainia villosa
Front Plant Sci 2022 Mar 28;13:860152.PMID:35432416DOI:10.3389/fpls.2022.860152.
Bornyl acetate (BA) is known as a natural aromatic monoterpene ester with a wide range of pharmacological and biological activities. Borneol acetyltransferase (BAT), catalyzing borneol and acetyl-CoA to synthesize BA, is alcohol acetyltransferase, which belongs to the BAHD super acyltransferase family, however, BAT, responsible for the biosynthesis of BA, has not yet been characterized. The seeds of Wurfbainia villosa (homotypic synonym: Amomum villosum) are rich in BA. Here we identified 64 members of the BAHD gene family from the genome of W. villosa using both PF02458 (transferase) and PF07247 (AATase) as Hidden Markov Model (HMM) to screen the BAHD genes. A total of sixty-four WvBAHDs are distributed on 14 chromosomes and nine unanchored contigs, clustering into six clades; three WvBAHDs with PF07247 have formed a separated and novel clade: clade VI. Twelve candidate genes belonging to clade I-a, I-b, and VI were selected to clone and characterize in vitro, among which eight genes have been identified to encode BATs acetylating at least one type of borneol to synthesize BA. All eight WvBATs can utilize (-)-borneol as substrates, but only five WvBATs can catalyze (+)-borneol, which is the endogenous borneol substrate in the seeds of W. villosa; WvBAT3 and WvBAT4 present the better catalytic efficiency on (+)-borneol than the others. The temporal and spatial expression patterns of WvBATs indicate that WvBAT3 and WvBAT4 are seed-specific expression genes, and their expression levels are correlated with the accumulation of BA, suggesting WvBAT3 and WvBAT4 might be the two key BATs for BA synthesis in the seeds of W. villosa. This is the first report on BAT responsible for the last biosynthetic step of BA, which will contribute to further studies on BA biosynthesis and metabolism engineering of BA in other plants or heterologous hosts.
Inhibition of lung inflammatory responses by Bornyl acetate is correlated with regulation of myeloperoxidase activity
J Surg Res 2014 Jan;186(1):436-45.PMID:24120240DOI:10.1016/j.jss.2013.09.003.
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 κB 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.