(+)-Borneol

Names

[ CAS No. ]:
464-43-7

[ Name ]:
(+)-Borneol

[Synonym ]:
oct-7-ene-2,5-dione
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (2S)-
oct-7-en-2,5-dion
EINECS 207-352-6
(2S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
(+)-BORNEOL
MFCD00066427

Biological Activity

[Description]:

(+)-Borneol (d-Borneol) is a natural bicyclic monoterpene used for analgesia and anesthesia in traditional Chinese medicine; enhances GABA receptor activity with an EC50 of 248 μM.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Inflammation/Immunology

Natural Products >> Terpenoids and Glycosides

[Target]

EC50: 248 μM (GABA receptor)[1]

[In Vitro]

(+)-Borneol is present in the essential oils of numerous medicinal plants, including valerian (Valeriana officinalis), chamomile (Matricaria chamomilla) and lavender (Lavandula officinalis). Extracts of these plants are used traditionally to relieve anxiety, restlessness and insomnia. (+)-Borneol is found to have a highly efficacious positive modulating action at GABAA receptors. (+)-Borneol enhances the action of low concentrations of GABA by more than 1000% (EC50=248 μM)[1].

[In Vivo]

(+)-Borneol has remarkable anti-hyperalgesic effects on neuropathic and inflammatory pain in animal models. Both oral administration (125, 250 or 500 mg/kg) and intrathecal injection (i.t.) (15, 30 and 60 μg) of (+)-Borneol reduce mechanical hypersensitivity dose-dependently in SNL and CFA models. The antihyperalgesic effects of (+)-Borneol are abolished by a selective GABAA receptor (GABAAR) antagonist bicuculline. (+)-Borneol (500 mg/kg, p.o. or 60 μg, i.t.) does not influence motor function[2]. After per oral application, (+)-Borneol is absorbed rapidly into the brain and could be determined 5 min after dosing. The maximal brain concentration (86.52 μg/g) is reached after 1 h post-dosing. (+)-Borneol could affect the contents of AA neurotransmitters in mice brain and the change in excitatory ratio leads to borneol's double side effects on the central nervous system[3].

[Animal admin]

Mice: Inflammatory pain is induced by injection of Complete Freund's adjuvant (CFA, 1 mg/mL). Ten min later mice are treated with (+)-Borneol (125, 250, 500 mg/kg) or vehicle. Mechanical hypersensitivity is then measured[2].

[References]

[1]. Granger RE, et al. (+)- And (-)-borneol: efficacious positive modulators of GABA action at human recombinantalpha1beta2gamma2L GABA(A) receptors. Biochem Pharmacol. 2005 Apr 1;69(7):1101-11.

[2]. Jiang J, et al. (+)-Borneol alleviates mechanical hyperalgesia in models of chronic inflammatory and neuropathic pain in mice. Eur J Pharmacol. 2015 Jun 15;757:53-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
212.0±0.0 °C at 760 mmHg

[ Melting Point ]:
206-209ºC(lit.)

[ Molecular Formula ]:
C₁₀H₁₈O

[ Molecular Weight ]:
154.249

[ Flash Point ]:
80.7±10.9 °C

[ Exact Mass ]:
154.135757

[ PSA ]:
20.23000

[ LogP ]:
2.71

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.502

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ED7060000

CHEMICAL NAME :: Borneol, (1R,2S,4R)- (+)-

CAS REGISTRY NUMBER :: 464-43-7

BEILSTEIN REFERENCE NO. :: 2038056

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H18-O

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,204,1989

Safety Information

[ Symbol ]:

GHS02

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H228

[ Precautionary Statements ]:
P210

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
F: Flammable;

[ Risk Phrases ]:
R11

[ Safety Phrases ]:
16-33-36-7/9

[ RIDADR ]:
UN 1312

[ WGK Germany ]:
3

[ RTECS ]:
ED7060000

[ Packaging Group ]:
III

[ Hazard Class ]:
4.1

[ HS Code ]:
2906199090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2906199090

[ Summary ]:
2906199090. cyclanic, cyclenic or cyclotherpenic alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl).

J. Phys. Chem. A 116(16) , 4097-107, (2012)

Relative kinetic techniques have been used to measure the rate coefficients for the reactions of oxygenated terpenes (menthol, borneol, fenchol, camphor, and fenchone) and cyclohexanol with hydroxyl r...

Treatment with cardiotonic pills(®) after ischemia-reperfusion ameliorates myocardial fibrosis in rats.

Microcirculation 20(1) , 17-29, (2013)

The present study was designed to evaluate whether CP was beneficial in alleviating myocardial fibrosis following I/R injury.Sprague-Dawley rats were subjected to 30 minutes occlusion of the LADCA, fo...

Borneol alleviates oxidative stress via upregulation of Nrf2 and Bcl-2 in SH-SY5Y cells.

Pharm. Biol. 51(1) , 30-5, (2013)

The β-amyloid (Aβ) peptide aggregation with accompanying oxidative stress plays the major role in the pathogenesis of Alzheimer's disease (AD). Some natural compounds, including borneol, shed promisin...