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Nootkatone, (+)-

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-N3002

  • Specification : 97%

  • CAS number : 4674-50-4

  • Formula : C15H22O

  • Molecular Weight : 218.3

  • PUBCHEM ID : 1268142

  • Volume : 100mg

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Catalogue Number

BF-N3002

Analysis Method

HPLC,NMR,MS

Specification

97%

Storage

-20℃

Molecular Weight

218.3

Appearance

Off-white Powder

Botanical Source

Alpinia oxyphylla

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CC(=O)C=C2C1(CC(CC2)C(=C)C)C

Synonyms

(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)-/4βh,5α-eremophila-1(10),11-dien-2-one/Nootkatone/Nootkatone, (+)-

IUPAC Name

(4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one

Density

1.0±0.1 g/cm3

Solubility

Ethanol; Chloroform; Methanol

Flash Point

142.1±18.7 °C

Boiling Point

318.6±42.0 °C at 760 mmHg

Melting Point

35-39ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2914290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:4674-50-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Article Available.


Description :

(+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells. PUMID/DOI:24704449 Biochem Biophys Res Commun. 2014 May 2;447(2):278-84. (+)-Nootkatone is the major component of Cyperus rotundus. (+)-Nootkatone has antiallergic, anti-inflammatory, and antiplatelet activities. The purpose of this study was to investigate the effect of (+)-Nootkatone on tumor necrosis factor α (TNF-α)/interferon γ (IFN-γ)-induced expression of Th2 chemokines in HaCaT cells. We found that (+)-Nootkatone inhibited the TNF-α/IFN-γ-induced expression of TARC/CCL17 and MDC/CCL22 mRNA in HaCaT cells. It also significantly inhibited TNF-α/IFN-γ-induced activation of nuclear factor kappa B (NF-κB), p38 mitogen-activated protein kinase (MAPK), and protein kinase Cζ (PKCζ). Furthermore, we showed that PKCζ and p38 MAPK contributed to the inhibition of TNF-α/IFN-γ-induced TARC/CCL17 and MDC/CCL22 expression by blocking IκBα degradation in HaCaT cells. Taken together, these results suggest that (+)-Nootkatone may suppress TNF-α/IFN-γ-induced TARC/CCL17 and MDC/CCL22 expression in HaCaT cells by inhibiting of PKCζ and p38 MAPK signaling pathways that lead to activation of NF-κB. We propose that (+)-Nootkatone may be a useful therapeutic candidate for inflammatory skin diseases such as AD. Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites. PUMID/DOI:21377882 Bioorg Med Chem. 2011 Apr 1;19(7):2464-9. Six metabolites were obtained as a result of microbial transformation of (+)-Nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9α-hydroxyNootkatone (2), (+)-(4R,5S,7R)-13-hydroxyNootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9α-hydroxyNootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksyNootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxyNootkatone (6) and (+)-(4R,5S,7R)-7,11,12-trihydroxyNootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-Nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated. Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK. PUMID/DOI:20501876 Am J Physiol Endocrinol Metab. 2010 Aug;299(2):E266-75. Nootkatone induced an increase in AMPKalpha1 and -alpha2 activity along with an increase in the AMP/ATP ratio and an increase the phosphorylation of AMPKalpha and the downstream target acetyl-CoA carboxylase (ACC), in C(2)C(12) cells. Nootkatone-induced activation of AMPK was possibly mediated both by LKB1 and Ca(2+)/calmodulin-dependent protein kinase kinase. Nootkatone also upregulated PPARgamma coactivator-1alpha in C(2)C(12) cells and C57BL/6J mouse muscle. In addition, administration of Nootkatone (200 mg/kg body wt) significantly enhanced AMPK activity, accompanied by LKB1, AMPK, and ACC phosphorylation in the liver and muscle of mice. Whole body energy expenditure evaluated by indirect calorimetry was also increased by Nootkatone administration. Long-term intake of diets containing 0.1% to 0.3% (wt/wt) Nootkatone significantly reduced high-fat and high-sucrose diet-induced body weight gain, abdominal fat accumulation, and the development of hyperglycemia, hyperinsulinemia, and hyperleptinemia in C57BL/6J mice. Furthermore, endurance capacity, evaluated as swimming time to exhaustion in BALB/c mice, was 21% longer in mice fed 0.2% Nootkatone than in control mice. These findings indicate that long-term intake of Nootkatone is beneficial toward preventing obesity and improving physical performance and that these effects are due, at least in part, to enhanced energy metabolism through AMPK activation in skeletal muscle and liver.