(-)-Borneol

Names

[ CAS No. ]:
464-45-9

[ Name ]:
(-)-Borneol

[Synonym ]:
L-BORNEOL
l-2-Bornanol
Borneol
endo-(1S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
endo-2-hydroxycamphane
2-Camphanol
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)-
L(-)-Borneol
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S,2R,4S)-
(1S,2R,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
[(1s)-endo]-(-)-borneol
2-Bornanol, endo-
EINECS 207-353-1
(1S-endo)-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol
(-)-Borneol
(−)-Borneol
Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1S,2R,4S)-
FEMA 2157
(1S)-endo-(-)-Borneol
BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, (1S-ENDO)-
2-bornanol
Bornan-2-ol
MFCD00003759
(？)-Borneol
endo-2-Bornanol
Linderol
endo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, endo-
endo-2-camphanol
ngaicamphor
bornel

Biological Activity

[Description]:

(-)-Borneol has a highly efficacious positive modulating action at GABA receptor with an EC50 of 237 μM.

[Related Catalog]:

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

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Neurological Disease

Natural Products >> Terpenoids and Glycosides

[Target]

EC50: 237 μM (GABA receptor)[1]

[In Vitro]

(-)-Borneol is an enantiomer of (+)-Borneol. (+)-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. At high concentrations (>1.5 mM), (-)-Borneol directly activates GABAA receptors producing 84% of the maximal GABA response indicative of a weak partial agonist action. (-)-Borneol produces dose-dependent positive modulation of the Cl- conductance generated by extremely low dose GABA at α1β2γ2L GABAA receptors[1].

[References]

[1]. IGranger 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.

[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 ]:
206-209 °C

[ Molecular Formula ]:
C₁₀H₁₈O

[ Molecular Weight ]:
154.249

[ Flash Point ]:
65.6±0.0 °C

[ Exact Mass ]:
154.135757

[ PSA ]:
20.23000

[ LogP ]:
2.71

[ Vapour density ]:
5.31 (vs air)

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

[ Index of Refraction ]:
1.502

[ Water Solubility ]:
INSOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DT5095000

CHEMICAL NAME :: Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)-

CAS REGISTRY NUMBER :: 464-45-9

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H18-O

MOLECULAR WEIGHT :: 154.28

WISWESSER LINE NOTATION :: L55 ATJ A1 A1 B1 CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,655,1978 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5800 mg/kg

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

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,655,1978

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H228-H317

[ Precautionary Statements ]:
P210-P280

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;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 ]:
S16-S36/37

[ RIDADR ]:
UN 1312 4.1/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
DT5095000

[ Packaging Group ]:
III

[ Hazard Class ]:
4.1

[ HS Code ]:
29061900

Synthetic Route

Click to get detail synthetic route

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...

Related Compounds

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