ar-turmerone
2-hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (6S)-
Identification
| Name | ar-turmerone |
| IUPAC | (6S)-2-methyl-6-(4-methylphenyl)hept-2-en-4-one |
| CAS Number | 532-65-0 |
| FDA UNII | 1944T899NO |
| Molecular Formula | C15 H20 O |
| Molecular Weight | 216.32360000 |
| MDL Number | MFCD09031381 |
| Nikkaji Number | J14.030I |
Regulatory
Physical Properties
| Assay | 90.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 325.00 to 326.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000226 mmHg @ 25.00 °C. (est) |
| Flash Point | 251.00 °F. TCC ( 121.67 °C. ) |
| logP (o/w) | 3.749 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for ar-turmerone usage levels up to | not for fragrance use. |
| Recommendation for ar-turmerone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2-
hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (6S)-
2-
hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (S)-
(S)-2-
methyl-6-(4-methyl phenyl)-2-hepten-4-one
(6S)-2-
methyl-6-(4-methylphenyl)hept-2-en-4-one
(+)-ar-
turmerone
(S)-ar-
turmerone
PubMed:
Insights from zebrafish and mouse models on the activity and safety of ar-turmerone as a potential drug candidate for the treatment of epilepsy.
PubMed:
GC-MS combined with chemometric techniques for the quality control and original discrimination of Curcumae longae rhizome: analysis of essential oils.
PubMed:
Antidermatophytic Properties of Ar-Turmerone, Turmeric Oil, and Curcuma longa Preparations.
PubMed:
An evaluation of antioxidant, anti-inflammatory, and antinociceptive activities of essential oil from Curcuma longa. L.
PubMed:
Biotransformation of turmerones by Aspergillus niger.
PubMed:
Optimisation of microencapsulation of turmeric extract for masking flavour.
PubMed:
Toxicity of Turmeric Extracts to the Termite Reticulitermes flavipes (Blattodea: Rhinotermitidae).
PubMed:
Larvicidal and Biting Deterrent Activity of Essential Oils of Curcuma longa, Ar-turmerone, and Curcuminoids Against Aedes aegypti and Anopheles quadrimaculatus (Culicidae: Diptera).
PubMed:
Natural products: Perspectives in the pharmacological treatment of gastrointestinal anisakiasis.
PubMed:
Aroma of Turmeric: Dependence on the Combination of Groups of Several Odor Constituents.
PubMed:
Cytotoxic active constituents of essential oils of Curcuma longa and Curcuma zanthorrhiza.
PubMed:
Cobalt-bisoxazoline-catalyzed asymmetric Kumada cross-coupling of racemic α-bromo esters with aryl Grignard reagents.
PubMed:
Essential oil content of the rhizome of Curcuma purpurascens Bl. (Temu Tis) and its antiproliferative effect on selected human carcinoma cell lines.
PubMed:
Liposomal formulation of turmerone-rich hexane fractions from Curcuma longa enhances their antileishmanial activity.
PubMed:
Suppression of Inflammatory cytokine production by ar-Turmerone isolated from Curcuma phaeocaulis.
PubMed:
Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour.
PubMed:
Aromatic-turmerone induces neural stem cell proliferation in vitro and in vivo.
PubMed:
The inhibitory effects of Curcuma longa L. essential oil and curcumin on Aspergillus flavus link growth and morphology.
PubMed:
Antidermatophytic Properties of Ar-Turmerone, Turmeric Oil, and Curcuma longa Preparations.
PubMed:
Simultaneous screening of four epidermal growth factor receptor antagonists from Curcuma longa via cell membrane chromatography online coupled with HPLC-MS.
PubMed:
Correlation between Chemical Composition of Curcuma domestica and Curcuma xanthorrhiza and Their Antioxidant Effect on Human Low-Density Lipoprotein Oxidation.
PubMed:
Curcumin combined with turmerones, essential oil components of turmeric, abolishes inflammation-associated mouse colon carcinogenesis.
PubMed:
Immune activation and antitumor response of ar-turmerone on P388D1 lymphoblast cell implanted tumors.
PubMed:
Maturation and upregulation of functions of murine dendritic cells (DCs) under the influence of purified aromatic-turmerone (AR).
PubMed:
Supercritical carbon dioxide extraction of aromatic turmerone from Curcuma longa Linn. induces apoptosis through reactive oxygen species-triggered intrinsic and extrinsic pathways in human hepatocellular carcinoma HepG2 cells.
PubMed:
Aromatic-turmerone's anti-inflammatory effects in microglial cells are mediated by protein kinase A and heme oxygenase-1 signaling.
PubMed:
Aromatic-turmerone attenuates invasion and expression of MMP-9 and COX-2 through inhibition of NF-κB activation in TPA-induced breast cancer cells.
PubMed:
Anti-inflammatory effects of aromatic-turmerone through blocking of NF-κB, JNK, and p38 MAPK signaling pathways in amyloid β-stimulated microglia.
PubMed:
Turmeric (Curcuma longa L.) volatile oil inhibits key enzymes linked to type 2 diabetes.
PubMed:
An evaluation of antioxidant, anti-inflammatory, and antinociceptive activities of essential oil from Curcuma longa. L.
PubMed:
Aromatic-turmerone inhibits α-MSH and IBMX-induced melanogenesis by inactivating CREB and MITF signaling pathways.
PubMed:
Biotransformation of turmerones by Aspergillus niger.
PubMed:
Anti-platelet effects of Curcuma oil in experimental models of myocardial ischemia-reperfusion and thrombosis.
PubMed:
Evaluation of in vitro anti-proliferative and immunomodulatory activities of compounds isolated from Curcuma longa.
PubMed:
Acetylcholinesterase inhibitory activity of volatile oil from Peltophorum dasyrachis Kurz ex Bakar (yellow batai) and Bisabolane-type sesquiterpenoids.
PubMed:
Activation of apoptotic protein in U937 cells by a component of turmeric oil.
PubMed:
Standardization and stability studies of neuroprotective lipid soluble fraction obtained from Curcuma longa.
PubMed:
Quantitative determination of eight components in rhizome (Jianghuang) and tuberous root (Yujin) of Curcuma longa using pressurized liquid extraction and gas chromatography-mass spectrometry.
PubMed:
Antiplatelet property of Curcuma longa L. rhizome-derived ar-turmerone.
PubMed:
Hypoglycemic effects of turmeric (Curcuma longa L. rhizomes) on genetically diabetic KK-Ay mice.
PubMed:
Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice.
PubMed:
Induction of apoptosis by ar-turmerone on various cell lines.
PubMed:
Stereospecific Pd(0)-catalyzed arylation of an allylic hydroxy phosphonate derivative: formal synthesis of (S)-(+)-ar-turmerone.
PubMed:
Extraction of essential oil and pigments from Curcuma longa [L] by steam distillation and extraction with volatile solvents.
PubMed:
Comparison of yield, composition, and antioxidant activity of turmeric (Curcuma longa L.) extracts obtained using various techniques.
PubMed:
Inhibitory effects of natural sesquiterpenoids isolated from the rhizomes of Curcuma zedoaria on prostaglandin E2 and nitric oxide production.
PubMed:
Suppressive effect of natural sesquiterpenoids on inducible cyclooxygenase (COX-2) and nitric oxide synthase (iNOS) activity in mouse macrophage cells.
PubMed:
Selective induction of apoptosis by ar-turmerone isolated from turmeric (Curcuma longa L) in two human leukemia cell lines, but not in human stomach cancer cell line.
PubMed:
Sesquiterpenoids from the rhizome of Curcuma zedoaria.
PubMed:
Essential oil composition and antimicrobial activity of three Zingiberaceae from S.Tomé e PrÃncipe.
PubMed:
Supercritical carbon dioxide extraction of turmeric (Curcuma longa).
PubMed:
Antibacterial activity of turmeric oil: a byproduct from curcumin manufacture.
PubMed:
Novel bioactivities of Curcuma longa constituents.