Nootkatone

Names

[ Name ]:
Nootkatone

[Synonym ]:
(4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
EINECS 225-124-4
MFCD00036591
4βh,5α-eremophila-1(10),11-dien-2-one
Nootkatone
Nootkatone, (+)-

Biological Activity

[Description]:

Nootkatone, a neuroprotective agent from Alpiniae Oxyphyllae Fructus, has antioxidant and anti-inflammatory effects[1]. Nootkatone improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vivo]

Nootkatone (10 mg/kg) group shows good performance in behavior experiments including Y-maze test and Morris water maze test. The results of histopathological examination and immunohistochemical analysis showed that LPS induced degeneration of neurons and activation of microglia particularly in hippocampus and Nootkatone (10 mg/kg) reversed these changes. Enzyme linked immunosorbent assay and western blot analysis also demonstrated that the model group had increased expression of IL-1β, IL-6, TNF-α, NLRP3 and NF-κB p65, especially in hippocampus relative to sham-operated group, and Nootkatone (10 mg/kg) decreased the high expression of these inflammatory cytokines[1].

[References]

[1]. Wang Y, et al. Nootkatone, a neuroprotective agent from Alpiniae Oxyphyllae Fructus, improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease. Int Immunopharmacol. 2018 Sep;62:77-85.

[2]. Wang Y, et al. Nootkatone, a neuroprotective agent from Alpiniae Oxyphyllae Fructus, improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease. Int Immunopharmacol. 2018 Sep;62:77-85.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
318.6±42.0 °C at 760 mmHg

[ Melting Point ]:
35-39ºC

[ Molecular Formula ]:
C₁₅H₂₂O

[ Molecular Weight ]:
218.335

[ Flash Point ]:
142.1±18.7 °C

[ Exact Mass ]:
218.167068

[ PSA ]:
17.07000

[ LogP ]:
3.84

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.503

[ Storage condition ]:
2-8°C

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

[ Water Solubility ]:
Slightly soluble in ethanol and chloroform. Partly soluble in water.

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase.

Appl. Microbiol. Biotechnol. 95(1) , 123-33, (2012)

Many terpenes and terpenoid compounds are known as bioactive substances with desirable fragrance and medicinal activities. Modification of such compounds to yield new derivatives with desired properti...

A-Z of nutritional supplements: dietary supplements, sports nutrition foods and ergogenic aids for health and performance--Part 27.

Br. J. Sports Med. 45(15) , 1246-8, (2011)

Anti-diarrheal constituents of Alpinia oxyphylla.

Fitoterapia 89 , 149-56, (2013)

Isolation, screening and in vivo assays have been used for evaluating anti-diarrhea bioactive of Alpinia oxyphylla. Preliminary experimental results showed that 95% ethanol extract and 90% ethanol elu...