Borneol

CAS# 507-70-0

Borneol

Catalog No. BCN4964----Order now to get a substantial discount!

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Quality Control of Borneol

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Chemical structure

Borneol

3D structure

Chemical Properties of Borneol

Cas No. 507-70-0 SDF Download SDF
PubChem ID 64685 Appearance Oil
Formula C10H18O M.Wt 154.25
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Synonyms DL-2-Bornanol;6627-72-1
Solubility DMSO : ≥ 100 mg/mL (648.30 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol
SMILES CC1(C2CCC1(C(C2)O)C)C
Standard InChIKey DTGKSKDOIYIVQL-UHFFFAOYSA-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
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 Borneol

The branch of Cinnamomum camphora (L) presl.

Biological Activity of Borneol

Description(+)-Borneol is a bicyclic monoterpene used for analgesia and anaesthesia in traditional Chinese and Japanese medicine, it and its enantiomer (-)-borneol have a highly efficacious positive modulating action at GABA(A) receptors at human recombinant alpha1beta2gamma2L GABA(A) receptors. Borneol specifically inhibits the nicotinic acetylcholine receptor (nAChR)-mediated effects in a noncompetitive way, can depress P-glycoprotein function by a NF-κB signaling mediated mechanism in a blood brain barrier in vitro model. Borneol has neuroprotection through the inhibition of IκBα-NF-κB and translocation signaling pathway, it also has an anti-cerebral ischemia effects. It can suppresse inflammatory responses in LPS-induced acute lung injury through inhibition of the NF-κB and MAPKs signaling pathways.
TargetsP-gp | NF-kB | ROS | NO | NOS | JNK | p65 | IkB | p38MAPK | ERK | TNF-α | GABA Receptor | AChR | IKK
In vitro

Protection by borneol on cortical neurons against oxygen-glucose deprivation/reperfusion: involvement of anti-oxidation and anti-inflammation through nuclear transcription factor κappaB signaling pathway.[Pubmed: 21168474]

Neuroscience. 2011 Mar 10;176:408-19.

Borneol, a terpene and bicyclic organic compound found in several species, can easily penetrate the blood-brain barrier (BBB) and helps the absorption of many agents through BBB in the brain, but there has been no study about its direct action on neurons in the CNS. In the present study, we used an in vitro ischemic model of oxygen-glucose deprivation followed by reperfusion (OGD/R) to investigate the neuroprotective effects of Borneol and the related mechanisms.
METHODS AND RESULTS:
We demonstrated that Borneol reversed OGD/R-induced neuronal injury, nuclear condensation, intracellular reactive oxygen species (ROS) generation, and mitochondrial membrane potential dissipation. The elevation of nitric oxide (NO), the increase of inducible nitric oxide synthase (iNOS) enzymatic activity and the upregulation of iNOS expression were also attenuated by Borneol. The inhibition of caspase-related apoptotic signaling pathway was consistently involved in the neuroprotection afforded by Borneol. Meanwhile, Borneol inhibited proinflammatory factor release and IκBα degradation, and blocked nuclear transcription factor κappaB (NF-κB) p65 nuclear translocation induced by OGD/R. On the other hand, Borneol did not show obvious effect on the inhibition of phospho-IKKα activation. Furthermore, it failed to affect the OGD/R-induced enhanced level of phospho-SAPK/JNK.
CONCLUSIONS:
In conclusion, our study indicated that Borneol protects against cerebral ischemia/reperfusion injury through multifunctional cytoprotective pathways. The mechanisms of this reversal from OGD/R may be involved in the alleviation of intracellular ROS and iNOS/NO pathway, inhibition of inflammatory factor release and depression of caspase-related apoptosis. Among these effects, the inhibition of IκBα-NF-κB and translocation signaling pathway might play a significant role in the neuroprotection of Borneol.

(+)- And (-)-borneol: efficacious positive modulators of GABA action at human recombinant alpha1beta2gamma2L GABA(A) receptors.[Pubmed: 15763546 ]

Biochem Pharmacol. 2005 Apr 1;69(7):1101-11.

(+)-Borneol is a bicyclic monoterpene used for analgesia and anaesthesia in traditional Chinese and Japanese medicine and is found in the essential oils of medicinal herbs, such as valerian. (+)-Borneol was found to have a highly efficacious positive modulating action at GABA(A) receptors, as did its enantiomer (-)-Borneol.
METHODS AND RESULTS:
The effects of these bicyclic monoterpenes alone and with GABA were evaluated at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes using two-electrode voltage-clamp electrophysiology. (+)-Borneol (EC(50) 248microM) and (-)-Borneol (EC(50) 237microM) enhanced the action of low concentrations of GABA by more than 1000%. These enhancing effects were highly dependent on the relative concentrations of the Borneol enantiomer and GABA, and were insensitive to flumazenil indicating that (+)- and (-)-Borneol were not acting at classical benzodiazepine sites. The maximal responses to GABA were enhanced 19% by (+)-Borneol and reduced 21% by (-)-Borneol. The Borneol analogues isoBorneol, (-)-bornyl acetate and camphor, produced less marked effects. At high concentrations (>1.5mM) (+)- and (-)-Borneol directly activated GABA(A) receptors producing 89% and 84%, respectively, of the maximal GABA response indicative of a weak partial agonist action. Although of lower potency, the highly efficacious positive modulatory actions of (+)- and (-)-Borneol on GABA responses were at least equivalent to that of the anaesthetic etomidate and much greater than that of diazepam or 5alpha-pregnan-3alpha-ol-20-one.
CONCLUSIONS:
The relatively rigid cage structure of these bicyclic monoterpenes and their high efficacy may aid in a greater understanding of molecular aspects of positive modulation of the activation of GABA(A) receptors.

In vivo

Borneol Depresses P-Glycoprotein Function by a NF-κB Signaling Mediated Mechanism in a Blood Brain Barrier in Vitro Model.[Pubmed: 26593909 ]

Int J Mol Sci. 2015 Nov 18;16(11):27576-88.

P-glycoprotein (P-gp) on brain microvascular endothelial cells (BMECs) that form the blood brain barrier (BBB), influences transportation of substances between blood and brain. The objective of this study was to characterize the effects of Borneol on P-gp efflux function on BBB and explore the potential mechanisms.
METHODS AND RESULTS:
We established an in vitro BBB model comprised of rat BMECs and astrocytes to measure the effects of Borneol on the known P-gp substrates transport across BBB, and examined the function and expression of P-gp in BMECs and the signaling pathways regulating P-gp expression. Borneol increased intracellular accumulation of Rhodamine 123, enhanced verapamil and digoxin across the BBB in vitro model, and depressed mdr1a mRNA and P-gp expression. Borneol could activate nuclear factor-κB (NF-κB) and inhibition of NF-κB with MG132 (carbobenzoxy-Leu-Leu-leucinal) and SN50 (an inhibitory peptide) obscuring the P-gp decreases induced by Borneol.
CONCLUSIONS:
These data suggested that Borneol depresses P-gp function in BMECs by a NF-κB signaling medicated mechanism in a BBB in vitro model.

Study on the anti-cerebral ischemia effect of borneol and its mechanism.[Pubmed: 24653571 ]

Afr J Tradit Complement Altern Med. 2013 Nov 2;11(1):161-4.

Borneol is the processed item from resin of Dryobalanops aromatica Gaertn. f. It can enhance the activity of antioxidant enzymes in brain tissue and reduce inflammatory response by improving the energy metabolism of ischemic brain regions, and thereby reduces brain tissue damage. The objective of this paper was to study the anti-cerebral ischemia effect of Borneol and its mechanism.
METHODS AND RESULTS:
The anti-cerebral ischemia effect of Borneol was studied by ligation of bilateral common carotid arteries (CCA), and vagus nerves in mice and the acute cerebral ischemia-reperfusion experiment in rats. Compared with the blank and solvent control groups, the Borneol low-; medium-; and high-dose groups can significantly prolong the gasping time of mice after decapitation, and extend the survival time of mice after ligation of bilateral CCA, and vagus nerves. Compared with the Xueshuantong injection group, the prolongation of survival time of mice after ligation of bilateral CCA, and vagus nerves was more apparent in the high-dose Borneol experimental group; each experimental group can significantly reduce the number of leukocyte infiltration, the number of ICAM-1-positive vessels, as well as the number of TNF-α-positive cells.
CONCLUSIONS:
Borneol has an anti-cerebral ischemia effect.

Protocol of Borneol

Kinase Assay

Inhibition of acetylcholine-mediated effects by borneol.[Pubmed: 12473382]

Biochem Pharmacol. 2003 Jan 1;65(1):83-90.

We previously reported that the aqueous extract from a medicinal plant Dryobalanops aromatica specifically inhibits the nicotinic acetylcholine receptor (nAChR) (Oh et al. Pharmacol Res 2000;42(6):559-64). Here, the effect of Borneol, the main constituent of D. aromatica, on nAChR activity was investigated in bovine adrenal chromaffin cells.
METHODS AND RESULTS:
Borneol inhibited a nAChR agonist 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP)-induced calcium increase with a half maximal inhibitory concentration (IC(50)) of 56+/-9 microM. In contrast, Borneol did not affect the calcium increases induced by high K+, veratridine, and bradykinin. The sodium increase induced by DMPP was also inhibited by Borneol with similar potency (49+/-12 microM), suggesting that the activity of nAChRs is inhibited by Borneol. Borneol inhibited DMPP-induced secretion of [3H]norepinephrine with an IC(50) of 70+/-12 microM. Carbon-fiber amperometry also confirmed the inhibition of DMPP-induced exocytosis by Borneol in single chromaffin cells. [3H]nicotine binding, however, was not affected by Borneol. The inhibitory effect by Borneol is more potent than the effect by lidocaine, a commonly used local anesthetic.
CONCLUSIONS:
The data suggest that Borneol specifically inhibits the nAChR-mediated effects in a noncompetitive way.

Animal Research

Modulation of LPS-stimulated pulmonary inflammation by Borneol in murine acute lung injury model.[Pubmed: 24566873]

Inflammation. 2014 Aug;37(4):1148-57.

The object of our study is to investigate the protective effects of Borneol on lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice.
METHODS AND RESULTS:
To determine the effects of Borneol on the histopathological changes in mice with ALI, inflammatory cell count in bronchoalveolar lavage fluid (BALF) and lung wet/dry weight ratio were measured in LPS-challenged mice, and lung histopathologic changes observed via paraffin section were assessed. Next, cytokine production induced by LPS in BALF and RAW 264.7 cells was measured by enzyme-linked imunosorbent assay (ELISA). To further study the mechanism of Borneol-protective effects on ALI, nuclear factor-kappaB (NF-κB) and mitogen-activated protein kinases (MAPKs) pathways were investigated. In the present study, Borneol obviously alleviated pulmonary inflammation by reducing inflammatory infiltration, histopathological changes, descended cytokine production, and pulmonary edema initiated by LPS. Furthermore, Borneol significantly suppressed phosphorylation of NF-κB/P65, IκBa, p38, JNK, and ERK.
CONCLUSIONS:
Taken together, our results suggest that Borneol suppressed inflammatory responses in LPS-induced acute lung injury through inhibition of the NF-κB and MAPKs signaling pathways. Borneol may be a promising potential preventive agent for acute lung injury treatment.

Borneol Dilution Calculator

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Borneol Molarity Calculator

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Preparing Stock Solutions of Borneol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.483 mL 32.4149 mL 64.8298 mL 129.6596 mL 162.0746 mL
5 mM 1.2966 mL 6.483 mL 12.966 mL 25.9319 mL 32.4149 mL
10 mM 0.6483 mL 3.2415 mL 6.483 mL 12.966 mL 16.2075 mL
50 mM 0.1297 mL 0.6483 mL 1.2966 mL 2.5932 mL 3.2415 mL
100 mM 0.0648 mL 0.3241 mL 0.6483 mL 1.2966 mL 1.6207 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 Borneol

(+)- And (-)-borneol: efficacious positive modulators of GABA action at human recombinant alpha1beta2gamma2L GABA(A) receptors.[Pubmed:15763546]

Biochem Pharmacol. 2005 Apr 1;69(7):1101-11.

(+)-Borneol is a bicyclic monoterpene used for analgesia and anaesthesia in traditional Chinese and Japanese medicine and is found in the essential oils of medicinal herbs, such as valerian. (+)-Borneol was found to have a highly efficacious positive modulating action at GABA(A) receptors, as did its enantiomer (-)-Borneol. The effects of these bicyclic monoterpenes alone and with GABA were evaluated at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes using two-electrode voltage-clamp electrophysiology. (+)-Borneol (EC(50) 248microM) and (-)-Borneol (EC(50) 237microM) enhanced the action of low concentrations of GABA by more than 1000%. These enhancing effects were highly dependent on the relative concentrations of the Borneol enantiomer and GABA, and were insensitive to flumazenil indicating that (+)- and (-)-Borneol were not acting at classical benzodiazepine sites. The maximal responses to GABA were enhanced 19% by (+)-Borneol and reduced 21% by (-)-Borneol. The Borneol analogues isoBorneol, (-)-bornyl acetate and camphor, produced less marked effects. At high concentrations (>1.5mM) (+)- and (-)-Borneol directly activated GABA(A) receptors producing 89% and 84%, respectively, of the maximal GABA response indicative of a weak partial agonist action. Although of lower potency, the highly efficacious positive modulatory actions of (+)- and (-)-Borneol on GABA responses were at least equivalent to that of the anaesthetic etomidate and much greater than that of diazepam or 5alpha-pregnan-3alpha-ol-20-one. The relatively rigid cage structure of these bicyclic monoterpenes and their high efficacy may aid in a greater understanding of molecular aspects of positive modulation of the activation of GABA(A) receptors.

Protection by borneol on cortical neurons against oxygen-glucose deprivation/reperfusion: involvement of anti-oxidation and anti-inflammation through nuclear transcription factor kappaappaB signaling pathway.[Pubmed:21168474]

Neuroscience. 2011 Mar 10;176:408-19.

Borneol, a terpene and bicyclic organic compound found in several species, can easily penetrate the blood-brain barrier (BBB) and helps the absorption of many agents through BBB in the brain, but there has been no study about its direct action on neurons in the CNS. In the present study, we used an in vitro ischemic model of oxygen-glucose deprivation followed by reperfusion (OGD/R) to investigate the neuroprotective effects of Borneol and the related mechanisms. We demonstrated that Borneol reversed OGD/R-induced neuronal injury, nuclear condensation, intracellular reactive oxygen species (ROS) generation, and mitochondrial membrane potential dissipation. The elevation of nitric oxide (NO), the increase of inducible nitric oxide synthase (iNOS) enzymatic activity and the upregulation of iNOS expression were also attenuated by Borneol. The inhibition of caspase-related apoptotic signaling pathway was consistently involved in the neuroprotection afforded by Borneol. Meanwhile, Borneol inhibited proinflammatory factor release and IkappaBalpha degradation, and blocked nuclear transcription factor kappaappaB (NF-kappaB) p65 nuclear translocation induced by OGD/R. On the other hand, Borneol did not show obvious effect on the inhibition of phospho-IKKalpha activation. Furthermore, it failed to affect the OGD/R-induced enhanced level of phospho-SAPK/JNK. In conclusion, our study indicated that Borneol protects against cerebral ischemia/reperfusion injury through multifunctional cytoprotective pathways. The mechanisms of this reversal from OGD/R may be involved in the alleviation of intracellular ROS and iNOS/NO pathway, inhibition of inflammatory factor release and depression of caspase-related apoptosis. Among these effects, the inhibition of IkappaBalpha-NF-kappaB and translocation signaling pathway might play a significant role in the neuroprotection of Borneol.

Study on the anti-cerebral ischemia effect of borneol and its mechanism.[Pubmed:24653571]

Afr J Tradit Complement Altern Med. 2013 Nov 2;11(1):161-4. eCollection 2014.

BACKGROUND: Borneol is the processed item from resin of Dryobalanops aromatica Gaertn. f. It can enhance the activity of antioxidant enzymes in brain tissue and reduce inflammatory response by improving the energy metabolism of ischemic brain regions, and thereby reduces brain tissue damage. The objective of this paper was to study the anti-cerebral ischemia effect of Borneol and its mechanism. MATERIALS AND METHODS: The anti-cerebral ischemia effect of Borneol was studied by ligation of bilateral common carotid arteries (CCA), and vagus nerves in mice and the acute cerebral ischemia-reperfusion experiment in rats. RESULTS: Compared with the blank and solvent control groups, the Borneol low-; medium-; and high-dose groups can significantly prolong the gasping time of mice after decapitation, and extend the survival time of mice after ligation of bilateral CCA, and vagus nerves. CONCLUSION: Compared with the Xueshuantong injection group, the prolongation of survival time of mice after ligation of bilateral CCA, and vagus nerves was more apparent in the high-dose Borneol experimental group; each experimental group can significantly reduce the number of leukocyte infiltration, the number of ICAM-1-positive vessels, as well as the number of TNF-alpha-positive cells. CONCLUSION: Borneol has an anti-cerebral ischemia effect.

Borneol Depresses P-Glycoprotein Function by a NF-kappaB Signaling Mediated Mechanism in a Blood Brain Barrier in Vitro Model.[Pubmed:26593909]

Int J Mol Sci. 2015 Nov 18;16(11):27576-88.

P-glycoprotein (P-gp) on brain microvascular endothelial cells (BMECs) that form the blood brain barrier (BBB), influences transportation of substances between blood and brain. The objective of this study was to characterize the effects of Borneol on P-gp efflux function on BBB and explore the potential mechanisms. We established an in vitro BBB model comprised of rat BMECs and astrocytes to measure the effects of Borneol on the known P-gp substrates transport across BBB, and examined the function and expression of P-gp in BMECs and the signaling pathways regulating P-gp expression. Borneol increased intracellular accumulation of Rhodamine 123, enhanced verapamil and digoxin across the BBB in vitro model, and depressed mdr1a mRNA and P-gp expression. Borneol could activate nuclear factor-kappaB (NF-kappaB) and inhibition of NF-kappaB with MG132 (carbobenzoxy-Leu-Leu-leucinal) and SN50 (an inhibitory peptide) obscuring the P-gp decreases induced by Borneol. These data suggested that Borneol depresses P-gp function in BMECs by a NF-kappaB signaling medicated mechanism in a BBB in vitro model.

Modulation of LPS-stimulated pulmonary inflammation by Borneol in murine acute lung injury model.[Pubmed:24566873]

Inflammation. 2014 Aug;37(4):1148-57.

The object of our study is to investigate the protective effects of Borneol on lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice. To determine the effects of Borneol on the histopathological changes in mice with ALI, inflammatory cell count in bronchoalveolar lavage fluid (BALF) and lung wet/dry weight ratio were measured in LPS-challenged mice, and lung histopathologic changes observed via paraffin section were assessed. Next, cytokine production induced by LPS in BALF and RAW 264.7 cells was measured by enzyme-linked imunosorbent assay (ELISA). To further study the mechanism of Borneol-protective effects on ALI, nuclear factor-kappaB (NF-kappaB) and mitogen-activated protein kinases (MAPKs) pathways were investigated. In the present study, Borneol obviously alleviated pulmonary inflammation by reducing inflammatory infiltration, histopathological changes, descended cytokine production, and pulmonary edema initiated by LPS. Furthermore, Borneol significantly suppressed phosphorylation of NF-kappaB/P65, IkappaBa, p38, JNK, and ERK. Taken together, our results suggest that Borneol suppressed inflammatory responses in LPS-induced acute lung injury through inhibition of the NF-kappaB and MAPKs signaling pathways. Borneol may be a promising potential preventive agent for acute lung injury treatment.

Inhibition of acetylcholine-mediated effects by borneol.[Pubmed:12473382]

Biochem Pharmacol. 2003 Jan 1;65(1):83-90.

We previously reported that the aqueous extract from a medicinal plant Dryobalanops aromatica specifically inhibits the nicotinic acetylcholine receptor (nAChR) (Oh et al. Pharmacol Res 2000;42(6):559-64). Here, the effect of Borneol, the main constituent of D. aromatica, on nAChR activity was investigated in bovine adrenal chromaffin cells. Borneol inhibited a nAChR agonist 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP)-induced calcium increase with a half maximal inhibitory concentration (IC(50)) of 56+/-9 microM. In contrast, Borneol did not affect the calcium increases induced by high K+, veratridine, and bradykinin. The sodium increase induced by DMPP was also inhibited by Borneol with similar potency (49+/-12 microM), suggesting that the activity of nAChRs is inhibited by Borneol. Borneol inhibited DMPP-induced secretion of [3H]norepinephrine with an IC(50) of 70+/-12 microM. Carbon-fiber amperometry also confirmed the inhibition of DMPP-induced exocytosis by Borneol in single chromaffin cells. [3H]nicotine binding, however, was not affected by Borneol. The inhibitory effect by Borneol is more potent than the effect by lidocaine, a commonly used local anesthetic. The data suggest that Borneol specifically inhibits the nAChR-mediated effects in a noncompetitive way.

Description

DL-Borneol is a racemic mixture of D-Borneol and L-Borneol. DL-Borneol is widely used for the treatment of cardiovascular and cerebrovascular diseases in China.

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