ar-turmerone
ar-turmerone Basic information
- Product Name:
- ar-turmerone
- Synonyms:
-
- (S)-ar-Turmerone
- TURMERONE, AR-(SH)
- 2-Methyl-6-p-tolylhept-2-en-4-one
- (S)-(+)-Turmerone
- (S)-2-Methyl-6-(4-methylphenyl)-2-hepten-4-one
- [S,(+)]-2-Methyl-6-p-tolyl-2-hepten-4-one
- (6S)-2-methyl-6-(4-methylphenyl)hept-2-en-4-one
- TURMERONE, AR-(SG)
- CAS:
- 532-65-0
- MF:
- C15H20O
- MW:
- 216.32
- Mol File:
- 532-65-0.mol
ar-turmerone Chemical Properties
- Boiling point:
- 326℃
- alpha
- D20 +82.21° (Rupe, Gassman); D22 +59.9° (c = 4.5 in hexane) (Sato)
- Density
- 0.945
- Flash point:
- 122℃
- storage temp.
- 2-8°C
- solubility
- Ethanol: Miscible
- form
- Liquid
- color
- Colorless to light yellow
- 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
- InChIKey
- NAAJVHHFAXWBOK-ZDUSSCGKSA-N
- SMILES
- C/C(/C)=C\C(=O)C[C@@H](C1=CC=C(C)C=C1)C
- LogP
- 3.749 (est)
Safety Information
- Hazard Codes
- Xi,N
- Risk Statements
- 36-43-51/53
- Safety Statements
- 36/37-61
- RIDADR
- UN 3082 9 / PGIII
- WGK Germany
- 3
- HS Code
- 29329990
ar-turmerone Usage And Synthesis
Uses
(+)-ar-Turmerone-d3 is the isotope labelled analog of (+)-ar-Turmerone. (+)-ar-Turmerone is an anti-tumor and immune activating agent, which maintains a cytotoxic effect in cancer cells. Antimicrobial agent.
Definition
ChEBI: A sesquiterpenoid that is 2-methylhept-2-en-4-one substituted by a 4-methylphenyl group at position 6. It has been isolated from Peltophorum dasyrachis.
Synthesis Reference(s)
The Journal of Organic Chemistry, 38, p. 2909, 1973 DOI: 10.1021/jo00956a039
Synthetic Communications, 11, p. 579, 1981 DOI: 10.1080/00397918108063627
Tetrahedron Letters, 20, p. 1519, 1979 DOI: 10.1016/S0040-4039(01)86195-5
in vivo
ar-Turmerone (100 mg/kg; p.o.; daily for 14 days) protects hippocampal and cortical neurons by downregulating the neuroinflammatory response, thereby alleviating spatial memory impairment in mice[5].
| Animal Model: | Repeated intraperitoneal injections of Lipopolysaccharides (LPS) (HY-D1056) in C57BL/6 mice. [5] |
| Dosage: | 100 mg/kg |
| Administration: | Oral gavage (p.o.); daily for 14 days |
| Result: | Mitigated the impairment of spatial learning and reference memory in mice. Reversed the effect of LPS induced TNF-α and IL-1βin hippocampal and cortex. The number of normal neurons and morphological characteristics were partially restored. Increased neuronal survival in both the hippocampus and cortex. |
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