ar-turmerone
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| Category | Antibiotics |
| Catalog number | BBF-04569 |
| CAS | 532-65-0 |
| Molecular Weight | 216.32 |
| Molecular Formula | C15H20O |
| Purity | ≥97% |
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Description
(+)-ar-Turmerone, a kind of aromatic compound, is a natural antibiotic used as an anti-tumor and immune-activating agent. It is known as a potent anti-venom against snake bites. It has been reported to promote stem cell proliferation, is a factor in nerve cell regeneration and brain injury, and has anti-inflammatory properties. It is widely used in anti-aging, removing wrinkles, whitening and lightening spots, antibacterial and anti-inflammatory, and anti-sensitivity repair products, and is compatible with lotion cream formulas, gel formulas and water formulas.
Specification
| Synonyms | (S)-ar-Turmerone; (6S)-2-Methyl-6-(4-methylphenyl)-2-hepten-4-one; Turmerone, (S)-ar-; ar-(+)-Turmerone; ar-Tumerone; (S)-2-Methyl-6-(4-methylphenyl)-2-hepten-4-one; (+)-(S)-ar-Turmerone |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (6S)-2-methyl-6-(4-methylphenyl)hept-2-en-4-one |
| Canonical SMILES | CC1=CC=C(C=C1)C(C)CC(=O)C=C(C)C |
| InChI | InChI=1S/C15H20O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-9,13H,10H2,1-4H3/t13-/m0/s1 |
| InChI Key | NAAJVHHFAXWBOK-ZDUSSCGKSA-N |
| Source | Curcuma longa (extracted from plant) |
Properties
| Appearance | Yellowish Oily Matter |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 325.7±21.0°C at 760 mmHg |
| Density | 0.945±0.1 g/cm3 |
| Solubility | Soluble in Hexane, Petrol Ether, Ethanol; Slightly soluble in Chloroform, DMSO, Ethyl Acetate, Methanol |
Reference Reading
1. Aromatic-turmerone ameliorates DSS-induced ulcerative colitis via modulating gut microbiota in mice
Chunlian Li, Weicheng Zhang, Xianyi Wu, Qiuyang Cai, Zekai Tan, Zhengyi Hong, Shiyuan Huang, Yanghe Yuan, Lewen Yao, Lanyue Zhang Inflammopharmacology. 2022 Aug;30(4):1283-1294. doi: 10.1007/s10787-022-01007-w. Epub 2022 Jul 6.
Curcuma longa L. is one of the traditional Chinese herbs in the list of medicinal and food homology. Aromatic-turmerone is the main ingredient in turmeric essential oil. The aim of the present study is to investigate the treatment of Aromatic-turmerone on DSS-included colitis and its regulatory effect on intestinal flora disorder. Male KM mice supplemented with different concentration of aromatic-turmerone and mesalazine are subjected to 2% DSS in drinking water to induce colitis. Colon and cecum contents were collected for colitis lesion evaluation and inflammation-related gene analysis and colon contents for gut microbiota. The results show that treatments with Aromatic-turmerone significantly prevents colon shortening, alleviates the damage of colonic tissue, and reduces colonic inflammatory cytokines TNF-α and COX-2. Furthermore, the 16S rDNA gene sequence data indicate that Aromatic-turmerone improve the abundance of bacterial species, maintain some beneficial bacteria, and reduce harmful bacteria. Aromatic-turmerone downregulates the colonic inflammatory cytokines and modulates the abundance of intestinal flora, which is conductive to ameliorates DSS-induced colitis. Regularly intake of the edible herb may be help to prevent ulcerative colitis-related diseases.
2. Extraction of curcuminoids and ar-turmerone from turmeric (Curcuma longa L.) using hydrophobic deep eutectic solvents (HDESs) and application as HDES-based microemulsions
Kantapich Kongpol, Namfa Sermkaew, Fonthip Makkliang, Sirinan Khongphan, Litavadee Chuaboon, Attapon Sakdamas, Seiichi Sakamoto, Waraporn Putalun, Gorawit Yusakul Food Chem. 2022 Dec 1;396:133728. doi: 10.1016/j.foodchem.2022.133728. Epub 2022 Jul 16.
The extraction of curcuminoids and aromatic (ar)-turmerone from Curcuma longa L. using organic solvents produces chemical waste, and is therefore incompatible with food applications. To address this issue, this study presents the design of hydrophobic deep eutectic solvents (HDESs) and HDES-based microemulsions. Using the response surface methodology (RSM), the optimal extraction conditions were identified as follows: HDES = OA:menthol (1:3.6 M ratio), solid-to-liquid ratio = 10:1 (mg/mL), and extraction duration = 90 min (prediction accuracy ≥ 85 %). Under these conditions, the HDES extraction yields of bisdemethoxycurcumin, demethoxycurcumin, curcumin, and ar-turmerone were 2.49 ± 0.25, 5.61 ± 0.45, 9.40 ± 0.86, and 3.83 ± 0.19 % (w/w, dry basis), respectively, while those obtained using the HDES-based microemulsion were 2.10 ± 0.18, 6.31 ± 0.48, 12.6 ± 1.20, and 2.58 ± 0.19 % (w/w, dry basis), respectively. The HDES and its microemulsions are more effective and environmentally friendly than conventional organic solvents for the extraction of curcuminoids and ar-turmerone, and these solvents are also compatible with food and pharmaceutical formulations.
3. Molecular insights on ar-turmerone as a structural, functional and pharmacophoric analogue of synthetic mosquito repellent DEET by comprehensive computational assessment
Priyashi Rao, Dweipayan Goswami, Rakesh M Rawal Sci Rep. 2022 Sep 16;12(1):15564. doi: 10.1038/s41598-022-19901-2.
Mosquitoes are vectors for a variety of infectious illnesses, and chemical synthetic insecticides have made it possible to control them effectively. Mosquito repellents are a typical means of keeping mosquitos at bay. Because of its main effectiveness of skin permeability, N,N-Diethyl-meta-toluamide (DEET) is one of the most extensively used mosquito repellents but a dangerous synthetic chemical. DEET was identified about a decade ago to inhibit mosquito's Odorant Binding Protein 1 (OBP1), impairing the mosquito's ability to recognise the host body odour. OBP1 has been identified as a possible target for the development of new mosquito repellents since its discovery. Essential oils from different plants, on the other hand, have been used to repel mosquitos since antiquity. One essential oil from the Curcuma longa (Zingiberales: Zingiberaceae) rhizome display mosquito repellent properties, according to the literature. Furthermore, one of the phytochemicals found in abundance in C. longa essential oil, ar-turmerone, exhibits mosquito repellency as comparable to synthetic DEET. Till date studies on in-silico interaction of natural ar-turmerone with OBP1, which we depict in our current work are scarce. Further, there exist no published reports demonstrating the literary evidence on detailed insights of interaction of DEET with OBP1 along with Molecular Dynamics (MD) simulation studies. We further performed detailed molecular investigations using pharmacophore analysis of ar-turmerone and compared it with DEET, where our findings in the current manuscript unveils for the first time that ar-turmerone is a functional, structural and pharmacophoric analogue of DEET.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
