borneol

Names

[ CAS No. ]:
507-70-0

[ Name ]:
borneol

[Synonym ]:
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2S,4R)-
exo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
2-Hydroxybornane
Borneol
bornyl alcohol
Baros camphor
methyl isobornyl ether
endo-borneol
(1R,2S,4R)-(+)-Borneol
(+)-Bornyl alcohol
isobornyl alcohol
EINECS 207-353-1
UNII:M89NIB437X
(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
(1R,2S,4R)-rel-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
MFCD00003759
Bhimsaim camphor
d-borneol
2-Hydroxycamphane
Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-
1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol
Dryobalanops camphor
Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
Borneo camphor
(1R,2S,4R)-borneol
(1R-endo)-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol
Camphol
Camphane, 2-hydroxy-
Malayan camphor
EINECS 208-080-0

Biological Activity

[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.

[Related Catalog]:

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

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Cardiovascular Disease

[In Vitro]

DL-Borneol increases intracellular accumulation of Rho123, and enhances P-gp substrates across the BBB in vitro, and also depresses mdr1a mRNA and P-gp expression. Furthermore, DL-Borneol could activate NF-κB and inhibition of NF-κB with MG132 and SN50 obscures the P-gp decreases induced by DL-Borneol. 10 μg/mL and 20 μg/mL DL-Borneol significantly increase phosphorylation of IκB expression at 30 min after treatment transiently. DL-Borneol treatment decreases P-gp expression in BMECs[1].

[In Vivo]

DL-Borneol significantly suppresses the process of epileptogenesis in PTZ-kindled mice. The biochemical alterations induced by PTZ kindling are ameliorated in DL-Borneol-treated animals which is indicated by decreased LPO and increased SOD, GSH, CAT levels. The distinct neuronal damage observed in the kindled group is counteracted by DL-Borneol. Furthermore, it decreases the levels of GFAP which is manifested by reduced immunostaining[2]. The pathological damages of ischemia-reperfusion have a significant impact on the pharmacokinetic traits of DL-Borneol and that there are some components in Xingnaojing inhibiting the absorption of DL-Borneol[3].

[Cell Assay]

Rho123 efflux assay is used to measure the activity of P-gp in BMECs according to previous methods. BMECs grown to confluency in 24-well plates are treated with 5 μg/mL, 10 μg/mL and 20 μg/mL DL-Borneol, DMSO, CsA for 2 h, or with 10 μg/mL and 20 μg/mL DL-Borneol for different times (30 min, 1 h, 2 h, and 4 h). Then BMECs are exposed to 5 μmol/L Rho123 in DMEM for 90 min. After incubation with Rho123, BMECs are washed with ice-cold PBS and solubilized in 1% NaOH. Fluorescence of Rho123 is measured with emission wavelength at 535 nm and excitation wavelength at 485 nm using a fluorescence spectrophotometer[1].

[Animal admin]

Rats: The pharmacokinetic study is performed 24 h after reperfusion in the model groups, i.e., 26 h after operation in the SO group. The XNJ subgroup rats are orally administered with XNJ decoction dissolved in 0.7% CMC-Na aqueous solution (10.00 ml/kg body weight (BW)). The pure DL-Borneol subgroup also receives gavages of DL-Borneol suspension (10.00 ml/kg BW). DL-Borneol and XNJ suspensions are administrated respectively at a dosage of 162.0 mg/kg of DL-Borneol. Then 0.5 ml plasma samples are collected into heparinized tubes by the puncture of the retro-orbital sinus at 5, 10, 20, 30, 45, 60, 90, 120, 180, 240, and 360 min separately following oral administration. After centrifugation at 6000 r/min for 10 min, plasma samples are stored at −20 °C and analyzed within one week[3]. Mice: Repeated administration of a subconvulsive dose of PTZ (35 mg/kg, i.p.) on every alternate day for 4 weeks produces kindling in mice. DL-Borneol (5, 10, and 25 mg/kg, i.p.) and diazepam (1 mg/kg, i.p.) are given as a pretreatment prior to each PTZ injection during the progression of kindling. Oxidative stress parameters such as superoxide dismutase (SOD), reduced glutathione (GSH), catalase (CAT), and lipid peroxidation (LPO) are assessed at the end of the study. Neuronal damage is assessed by hematoxylin and eosin staining technique. GFAP is also evaluated in the hippocampus region of the brain by using immunohistochemistry[2].

[References]

[1]. Fan X, et al. Borneol Depresses P-Glycoprotein Function by a NF-κB Signaling Mediated Mechanism in a Blood Brain Barrier in Vitro Model. Int J Mol Sci. 2015 Nov 18;16(11):27576-88.

[2]. Tambe R, et al. Antiepileptogenic effects of borneol in pentylenetetrazole-induced kindling in mice. Naunyn Schmiedebergs Arch Pharmacol. 2016 May;389(5):467-75.

[3]. Xu P, et al. Comparative pharmacokinetics of borneol in cerebral ischemia-reperfusion and sham-operated rats. J Zhejiang Univ Sci B. 2014 Jan;15(1):84-91.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.011

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

[ Melting Point ]:
206-207ºC

[ Molecular Formula ]:
C₁₀H₁₈O

[ Molecular Weight ]:
154.249

[ Flash Point ]:
65 ºC

[ 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

[ Stability ]:
Stable. Highly flammable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ED7000000

CHEMICAL NAME :: Borneol

CAS REGISTRY NUMBER :: 507-70-0

LAST UPDATED :: 199710

DATA ITEMS CITED :: 8

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 :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1059 mg/kg

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

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

MUTATION DATA

TYPE OF TEST :: DNA repair

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 10 mg/disc

REFERENCE :: OIGZDE Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M3906 No. of Facilities: 599 (estimated) No. of Industries: 11 No. of Occupations: 24 No. of Employees: 6733 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M3906 No. of Facilities: 1731 (estimated) No. of Industries: 12 No. of Occupations: 13 No. of Employees: 10168 (estimated) No. of Female Employees: 1230 (estimated)

Safety Information

[ Hazard Codes ]:
F;Xn

[ Risk Phrases ]:
R11;R22

[ Safety Phrases ]:
16-36/37

[ RIDADR ]:
UN 1312

[ WGK Germany ]:
2

[ RTECS ]:
DT5095000

[ Packaging Group ]:
III

[ Hazard Class ]:
4.1

[ HS Code ]:
2906199090

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%