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| Other Sizes |
| Targets |
Human Endogenous Metabolite
(-)-Bornyl acetate targets fungal cells, exhibiting antifungal activity. The compound's antifungal mechanism likely involves disruption of the fungal cell membrane, leading to increased permeability and cell death. (-)-Bornyl acetate may also inhibit the growth of fungi by interfering with key metabolic pathways. As a terpenoid, the compound may interact with membrane lipids and proteins, affecting membrane fluidity and function. The compound's antifungal activity is less potent than that of its (+)-enantiomer, consistent with its classification as a less active isomer. (-)-Bornyl acetate may also have other biological activities, including antimicrobial and insecticidal properties. |
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| ln Vitro |
In comparison to seedlings exposed to ()-bornyl acetate, the wavy roots of the former have a considerable lengthening[1]. When separately administered to barley seedlings, (-)-Bornyl acetate (L-bornyl acetate) decreased powdery mildew infection in comparison to ether-free controls[2].
In vitro, (-)-bornyl acetate has demonstrated antifungal activity against various fungal species. The compound's activity is typically assessed using agar diffusion or broth microdilution methods to determine the minimum inhibitory concentration (MIC) against fungi such as Candida, Aspergillus, and dermatophytes. (-)-Bornyl acetate is also used in fragrance and flavor research, where its sensory properties are characterized. The compound's in vitro activities are concentration-dependent, with higher concentrations achieving greater antifungal effects. (-)-Bornyl acetate may also exhibit antimicrobial activity against bacteria and other microorganisms. |
| ln Vivo |
In vivo, (-)-bornyl acetate is used in cosmetic and cleaning products for its antifungal and antimicrobial properties. The compound's safety and efficacy in these applications have been evaluated in various studies. (-)-Bornyl acetate is also used in traditional medicine and aromatherapy for its potential health benefits, although clinical evidence is limited. The compound's in vivo effects on fungal infections have not been extensively characterized, but its antifungal activity suggests potential for topical applications. Further studies are needed to fully evaluate the efficacy of (-)-bornyl acetate in vivo.
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| Enzyme Assay |
In vitro antifungal assays for (-)-bornyl acetate are performed using standard broth microdilution or agar dilution methods to determine the minimum inhibitory concentration (MIC) against fungal strains. Fungi are cultured in appropriate media (e.g., Sabouraud dextrose broth) and treated with serial dilutions of (-)-bornyl acetate (typically 0.1-100 μg/mL). The MIC is determined as the lowest concentration that inhibits visible growth after 48-72 hours of incubation. The minimum fungicidal concentration (MFC) is determined by subculturing from wells showing no visible growth onto agar plates. Zone of inhibition assays are performed by placing compound-impregnated discs on agar plates seeded with fungi. The compound's activity is compared to positive controls (known antifungal agents).
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| Cell Assay |
In vitro cell-based assays for (-)-bornyl acetate are performed using fungal cultures to assess antifungal activity. Fungi are grown in liquid media and treated with (-)-bornyl acetate at various concentrations. Growth inhibition is monitored by measuring optical density over time or by assessing colony-forming units (CFUs). The compound's effects on fungal cell membrane integrity can be assessed using fluorescent dyes such as propidium iodide. In mammalian cell lines, the compound's cytotoxicity is assessed to determine the selectivity index. The compound's effects on cell viability are assessed using MTT or LDH release assays.
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| Animal Protocol |
In vivo animal studies with (-)-bornyl acetate are limited, as the compound is primarily used in cosmetic and cleaning products rather than as a therapeutic agent. However, the compound's antifungal activity has been studied in animal models of fungal infection, where it is applied topically to infected skin or mucous membranes. The compound's efficacy in reducing fungal load and improving clinical signs is assessed. The compound's safety and tolerability are also evaluated. The compound's in vivo effects on fungal infections depend on the concentration, formulation, and application site.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
This study used radiolabeled components to determine the dermal absorption of camphene, isoborneol acetate, limonene, menthol, and α-pinene from a pinimenthol bath in animals. Pharmacokinetic measurements showed that all test components reached peak plasma concentrations 10 minutes after the onset of dermal absorption. No preferential absorption was observed for any component. Ten minutes after dermal absorption, plasma concentrations of all components were positively correlated with skin contact area. Metabolism/Metabolites Isoborneol acetate is rapidly hydrolyzed (within hours) in the first step of its biochemical pathway to produce isoborneol. This alcohol will bind to glucuronic acid and be excreted in the urine (expected within hours to days). Pharmacokinetic properties of (-)-bornyl acetate are not well-characterized, as the compound is primarily used in topical and fragrance applications rather than as a systemic therapeutic agent. As a lipophilic terpenoid, (-)-bornyl acetate is expected to be absorbed through the skin and mucous membranes. The compound is metabolized in the liver and excreted via the kidneys and bile. The compound's half-life and clearance would need to be determined for specific applications. For research use, (-)-bornyl acetate is stored at -20°C and protected from light. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Identification and Uses: Isoborneol acetate is used in soaps, detergents, creams, lotions, and perfumes. Human Studies: Maximum dose tests were conducted on 25 volunteers. No sensitization was observed when the substance was tested at a 10% concentration. Animal Studies: Mild irritation was observed when undiluted isoborneol acetate was applied to intact or abraded rabbit skin and left closed for 24 hours. Rats were administered isoborneol acetate daily at doses of 0, 15, 90, or 270 mg/kg body weight for 13 weeks. Male rats showed nephrotoxicity at doses of 90 mg/kg and 270 mg/kg/day, and hepatotoxicity at a dose of 270 mg/kg. In single-generation breeding studies in rats, isoborneol acetate did not exhibit developmental toxicity. Throughout the administration period, both male and female parental rats in the 100 and/or 300 mg/kg/day dose groups showed an increased incidence of excessive salivation, while female rats in the gestational 300 mg/kg/day dose group had a lower incidence of small amounts of urine staining their abdominal fur. Non-human toxicity values Rabbit dermal LD50 >20 g/kg Rats oral LD50 >10 g/kg Mice oral LD50 3100 mg/kg Rats oral LD50 9050 mg/kg (-)-Bornyl acetate is generally recognized as safe (GRAS) for use in food, cosmetics, and fragrances. The compound is well-tolerated at the concentrations used in consumer products. However, as with all essential oil components, (-)-bornyl acetate may cause skin irritation or allergic reactions in sensitive individuals. Ingestion of large amounts may cause gastrointestinal irritation. As a research chemical, standard safety precautions should be followed when handling (-)-bornyl acetate. The compound is for research use only and not for human therapeutic applications. |
| References |
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| Additional Infomation |
It has been reported that artemisia, turmeric, and other organisms with relevant data contain borneol acetate.
Mechanism of Action One possible explanation for the nephrotoxicity observed in males rather than females is the accumulation of α-2u-globulin, a protein that appears to contribute to the formation of renal tubular tumors in the kidneys of male rats. (-)-Bornyl acetate is a naturally occurring terpenoid found in various essential oils, including hyssop oil, pine oil, and rosemary oil. The compound is used in the fragrance and flavor industry for its pleasant, pine-like odor. (-)-Bornyl acetate is also used as a starting material for the synthesis of camphor and other terpenoid compounds. The compound's antifungal and antimicrobial properties make it useful in cosmetic and cleaning products for disinfection purposes. (-)-Bornyl acetate's role in the synthesis of (-)-englerin A, an anti-cancer agent, highlights its potential in pharmaceutical research. The compound is available from chemical suppliers for research purposes. |
| Molecular Formula |
C12H20O2
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|---|---|
| Molecular Weight |
196.29
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| Exact Mass |
196.146
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| CAS # |
5655-61-8
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| Related CAS # |
Bornyl acetate;76-49-3;(+)-Bornyl acetate;20347-65-3
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| PubChem CID |
6448
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
223.5±0.0 °C at 760 mmHg
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| Melting Point |
29ºC
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| Flash Point |
84.4±0.0 °C
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| Vapour Pressure |
0.1±0.4 mmHg at 25°C
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| Index of Refraction |
1.480
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| LogP |
3.6
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
270
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=O)O[C+]12(C)C(C)(C)CCC(C2)C1
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| InChi Key |
KGEKLUUHTZCSIP-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
(1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl) acetate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 100 mg/mL (509.45 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (12.74 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0945 mL | 25.4725 mL | 50.9450 mL | |
| 5 mM | 1.0189 mL | 5.0945 mL | 10.1890 mL | |
| 10 mM | 0.5095 mL | 2.5473 mL | 5.0945 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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