Isoborneol

CAS# 124-76-5

Isoborneol

2D Structure

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3D structure

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Isoborneol

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Chemical Properties of Isoborneol

Cas No. 124-76-5 SDF Download SDF
PubChem ID 6321405 Appearance Powder
Formula C10H18O M.Wt 154.3
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
SMILES CC1(C2CCC1(C(C2)O)C)C
Standard InChIKey DTGKSKDOIYIVQL-MRTMQBJTSA-N
Standard InChI InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/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 Isoborneol

The leaves of Blumea balsamifera.

Biological Activity of Isoborneol

DescriptionIsoborneol shows neuroprotective, antioxidant, and repellent effects, it shows dual viricidal activity against herpes simplex virus 1 (HSV-1).
TargetsHSV | Bcl-2/Bax | Caspase | PKC | JNK | ROS
In vitro

Antiviral properties of isoborneol, a potent inhibitor of herpes simplex virus type 1.[Pubmed: 10517310]

Antiviral Res. 1999 Sep;43(2):79-92.

Isoborneol, a monoterpene and a component of several plant essential oils, showed dual viricidal activity against herpes simplex virus 1 (HSV-1).
METHODS AND RESULTS:
First, it inactivated HSV-1 by almost 4 log10 values within 30 min of exposure, and second, Isoborneol at a concentration of 0.06% completely inhibited viral replication, without affecting viral adsorption. Isoborneol did not exhibit significant cytotoxicity at concentrations ranging between 0.016% and 0.08% when tested against human and monkey cell lines. Isoborneol specifically inhibited glycosylation of viral polypeptides based on the following data: (1) the mature fully glycosylated forms of two viral glycoproteins gB and gD were not detected when the virus was replicated in the presence of Isoborneol, (2) no major changes were observed in the glycosylation pattern of cellular polypeptides between untreated and Isoborneol treated Vero cells, (3) Isoborneol did not affect the glycosylation of gB produced from a copy of the gB gene resident in the cellular genome, and (4) other monoterpenes such as 1,8-cineole and borneol, a stereoisomer of Isoborneol, did not inhibit HSV-1 glycosylation.

Repellent effects of isoborneol on subterranean termites (Isoptera: Rhinotermitidae) in soils of different composition[Pubmed: 14503600]

J Econ Entomol. 2003 Aug;96(4):1267-74.


METHODS AND RESULTS:
The repellence of the plant-derived bicyclic monoterpenoid Isoborneol on subterranean termites was assessed in short-term laboratory bioassays. Depending on concentration, application of Isoborneol to different soil types was efficient in creating repellent soil barriers, which were not penetrated by workers of Reticulitermes santonensis De Feytaud or R. flavipes Kollar within 2 wk after adding the substance to the substrate. Isoborneol-treated barriers did not affect termite survival. The bioavailability of the active ingredient decreased with increasing clay content of the soil.
CONCLUSIONS:
Evaporation of Isoborneol from treated soil increased with increasing particle size of the substrate and could be reduced by covering the soil surface.

Protocol of Isoborneol

Cell Research

Protective effect of (+/-) isoborneol against 6-OHDA-induced apoptosis in SH-SY5Y cells.[Pubmed: 17975304 ]

Cell Physiol Biochem. 2007;20(6):1019-32.

Oxidative stress caused by dopamine (DA) may play an important role in the pathogenesis of Parkinson's disease (PD). (+/-) Isoborneol is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and is a known antioxidant.
METHODS AND RESULTS:
In this study, we investigated the neuroprotective effect of Isoborneol against 6-hydroxydopamine (6-OHDA)-induced cell death in human neuroblastoma SH-SY5Y cells. Pretreatment of SH-SY5Y cells with Isoborneol significantly reduced 6-OHDA-induced generation of reactive oxygen species (ROS) and 6-OHDA-induced increases in intracellular calcium. Furthermore, apoptosis induced by 6-OHDA was reversed by Isoborneol treatment. Isoborneol protected against 6-OHDA-induced increases in caspase-3 activity and cytochrome C translocation into the cytosol from mitochondria. Isoborneol prevented 6-OHDA from decreasing the Bax/Bcl-2 ratio. We also observed that Isoborneol decreased the activation of c-Jun N-terminal kinase and induced activation of protein kinase C (PKC) which had been suppressed by 6-OHDA.
CONCLUSIONS:
Our results indicate that the protective function of Isoborneol is dependent upon its antioxidant potential and strongly suggest that Isoborneol may be an effective treatment for neurodegenerative diseases associated with oxidative stress.

Structure Identification
Asian Journal of Chemistry, 2014, 26(4):997-1001.

Determination of (-)-Borneol, Camphor and Isoborneol in Blumea balsamifera (L.) DC. Leaves by Simultaneous Ultrasonic and Microwave Assisted Extraction and Gas Chromatography[Reference: WebLink]


METHODS AND RESULTS:
In present work, simultaneous ultrasonic and microwave assisted extraction followed by GC-FID was developed for quantitative analysis of the bioactive components of (-)-borneol, camphor and Isoborneol in Blumea balsamifera leaves. After systematical investigation, the optimal experimental parameters microwave power (100 W) and extraction time (30 s) were investigated. The optimized method provided satisfactory linearity, precision, stability and recovery. The proposed method was applied for determination of three target compounds in leaves samples from 14 different times of harvest period. The variations of three target compounds were monitored and the result demonstrates (-)-borneol content of leaves was higher level from mid-October to next January.
CONCLUSIONS:
It has been shown that the proposed ultrasonic and microwave assisted extraction-GC-FID is a simple, rapid and reliable method for quantitative analysis of (-)-borneol, camphor and Isoborneol in B. balsamifera leaves and a potential tool for quality assessment of B. balsamifera leaves.

Isoborneol Dilution Calculator

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Isoborneol Molarity Calculator

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Preparing Stock Solutions of Isoborneol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4809 mL 32.4044 mL 64.8088 mL 129.6176 mL 162.022 mL
5 mM 1.2962 mL 6.4809 mL 12.9618 mL 25.9235 mL 32.4044 mL
10 mM 0.6481 mL 3.2404 mL 6.4809 mL 12.9618 mL 16.2022 mL
50 mM 0.1296 mL 0.6481 mL 1.2962 mL 2.5924 mL 3.2404 mL
100 mM 0.0648 mL 0.324 mL 0.6481 mL 1.2962 mL 1.6202 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 Isoborneol

Repellent effects of isoborneol on subterranean termites (Isoptera: Rhinotermitidae) in soils of different composition.[Pubmed:14503600]

J Econ Entomol. 2003 Aug;96(4):1267-74.

The repellence of the plant-derived bicyclic monoterpenoid Isoborneol on subterranean termites was assessed in short-term laboratory bioassays. Depending on concentration, application of Isoborneol to different soil types was efficient in creating repellent soil barriers, which were not penetrated by workers of Reticulitermes santonensis De Feytaud or R. flavipes Kollar within 2 wk after adding the substance to the substrate. Isoborneol-treated barriers did not affect termite survival. The bioavailability of the active ingredient decreased with increasing clay content of the soil. Evaporation of Isoborneol from treated soil increased with increasing particle size of the substrate and could be reduced by covering the soil surface.

Protective effect of (+/-) isoborneol against 6-OHDA-induced apoptosis in SH-SY5Y cells.[Pubmed:17975304]

Cell Physiol Biochem. 2007;20(6):1019-32.

Oxidative stress caused by dopamine (DA) may play an important role in the pathogenesis of Parkinson's disease (PD). (+/-) Isoborneol is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and is a known antioxidant. In this study, we investigated the neuroprotective effect of Isoborneol against 6-hydroxydopamine (6-OHDA)-induced cell death in human neuroblastoma SH-SY5Y cells. Pretreatment of SH-SY5Y cells with Isoborneol significantly reduced 6-OHDA-induced generation of reactive oxygen species (ROS) and 6-OHDA-induced increases in intracellular calcium. Furthermore, apoptosis induced by 6-OHDA was reversed by Isoborneol treatment. Isoborneol protected against 6-OHDA-induced increases in caspase-3 activity and cytochrome C translocation into the cytosol from mitochondria. Isoborneol prevented 6-OHDA from decreasing the Bax/Bcl-2 ratio. We also observed that Isoborneol decreased the activation of c-Jun N-terminal kinase and induced activation of protein kinase C (PKC) which had been suppressed by 6-OHDA. Our results indicate that the protective function of Isoborneol is dependent upon its antioxidant potential and strongly suggest that Isoborneol may be an effective treatment for neurodegenerative diseases associated with oxidative stress.

Antiviral properties of isoborneol, a potent inhibitor of herpes simplex virus type 1.[Pubmed:10517310]

Antiviral Res. 1999 Sep;43(2):79-92.

Isoborneol, a monoterpene and a component of several plant essential oils, showed dual viricidal activity against herpes simplex virus 1 (HSV-1). First, it inactivated HSV-1 by almost 4 log10 values within 30 min of exposure, and second, Isoborneol at a concentration of 0.06% completely inhibited viral replication, without affecting viral adsorption. Isoborneol did not exhibit significant cytotoxicity at concentrations ranging between 0.016% and 0.08% when tested against human and monkey cell lines. Isoborneol specifically inhibited glycosylation of viral polypeptides based on the following data: (1) the mature fully glycosylated forms of two viral glycoproteins gB and gD were not detected when the virus was replicated in the presence of Isoborneol, (2) no major changes were observed in the glycosylation pattern of cellular polypeptides between untreated and Isoborneol treated Vero cells, (3) Isoborneol did not affect the glycosylation of gB produced from a copy of the gB gene resident in the cellular genome, and (4) other monoterpenes such as 1,8-cineole and borneol, a stereoisomer of Isoborneol, did not inhibit HSV-1 glycosylation.

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