トロポロン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/09/18 09:20:04」(JST)
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Tropolone[1] |
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IUPAC name
2-Hydroxy-2,4,6-cycloheptatrien-1-one
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Other names
2-Hydroxytropone; Purpurocatechol
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Identifiers |
CAS number |
533-75-5 Y |
PubChem |
10789 |
ChemSpider |
10333 N |
UNII |
7L6DL16P1T N |
EC number |
208-577-2 |
KEGG |
C15474 N |
MeSH |
D014334 |
ChEMBL |
CHEMBL121188 N |
Jmol-3D images |
Image 1 |
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InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9) N
Key: MDYOLVRUBBJPFM-UHFFFAOYSA-N N
InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
Key: MDYOLVRUBBJPFM-UHFFFAOYAW
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Properties |
Molecular formula |
C7H6O2 |
Molar mass |
122.12 g/mol |
Melting point |
50–52 °C |
Boiling point |
80–84 °C (0.1 mmHg) |
Acidity (pKa) |
6.89 (and -0.5 for conjugate acid) |
Hazards |
S-phrases |
S22 S24/25 |
Flash point |
112 °C (234 °F; 385 K) |
Related compounds |
Related compounds |
Hinokitiol (4-isopropyl-tropolone) |
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
N (verify) (what is: Y/N?) |
Infobox references |
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Tropolone is a derivative of tropone with a hydroxyl group in the 2-position.
Two methods for the synthesis of tropolone are by bromination of 1,2-cycloheptanedione with N-bromosuccinimide followed by dehydrohalogenation at elevated temperatures and by acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine.
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It is a grape polyphenol oxidase inhibitor.[2]
[3]
References
- ^ Tropolone at Sigma-Aldrich
- ^ Time-dependent inhibition of grape polyphenol oxidase by tropolone. Edelmira Valero, Manuela Garcia-Moreno, Ramon Varon and Francisco Garcia-Carmona, J. Agric. Food Chem., 1991, 39 (6), pp 1043–1046, doi:10.1021/jf00006a007
- ^ Chedgy, Russell. Secondary metabolites of Western red cedar (Thuja plicata): their biotechnological applications and role in conferring natural durability. LAP Lambert Academic Publishing, 2010, ISBN 3-8383-4661-0, ISBN 978-3-8383-4661-8
English Journal
- Tropolone as a High-Performance Robust Anchoring Group for Dye-Sensitized Solar Cells.
- Higashino T1, Fujimori Y1, Sugiura K1, Tsuji Y1, Ito S2, Imahori H3,4.
- Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2015 Jun 16. doi: 10.1002/anie.201502951. [Epub ahead of print]
- A tropolone group has been employed for the first time as an anchoring group for dye-sensitized solar cells (DSSCs). The DSSC based on a porphyrin, YD2-o-C8T, with a tropolone moiety exhibited a power-conversion efficiency of 7.7 %, which is only slightly lower than that observed for a reference p
- PMID 26080034
- Exploring the size adaptability of the B ring binding zone of the colchicine site of tubulin with para-nitrogen substituted isocombretastatins.
- Jiménez C1, Ellahioui Y2, Álvarez R1, Aramburu L1, Riesco A1, González M1, Vicente A1, Dahdouh A3, Ibn Mansour A3, Jiménez C4, Martín D4, Sarmiento RG4, Medarde M1, Caballero E1, Peláez R5.
- European journal of medicinal chemistry.Eur J Med Chem.2015 Jun 4;100:210-222. doi: 10.1016/j.ejmech.2015.05.047. [Epub ahead of print]
- We have synthesized and assayed dimethylaminophenyl, pyrrolidin-1-ylphenyl and carbazole containing phenstatins and isocombretastatins as analogues of the highly potent indoleisocombretastatins with extended or reduced ring sizes. This is an attempt to explore beyond the structural constraints of th
- PMID 26092446
- Antiproliferative Activity of Hinokitiol, a Tropolone Derivative, Is Mediated via the Inductions of p-JNK and p-PLCγ1 Signaling in PDGF-BB-Stimulated Vascular Smooth Muscle Cells.
- Yang PS1,2,3, Wang MJ4,5, Jayakumar T6, Chou DS7, Ko CY8, Hsu MJ9, Hsieh CY10.
- Molecules (Basel, Switzerland).Molecules.2015 May 7;20(5):8198-212. doi: 10.3390/molecules20058198.
- Abnormal proliferation of vascular smooth muscle cells (VSMCs) is important in the pathogenesis of vascular disorders such as atherosclerosis and restenosis. Hinokitiol, a tropolone derivative found in Chamacyparis taiwanensis, has been found to exhibit anticancer activity in a variety of cancers th
- PMID 25961161
Japanese Journal
- Synthesis of a Trinuclear Tropolone-Palladium(II) Macrocycle and its C60 Inclusion Properties
- Otani Hiroyuki,Sumi Chisaki,Shimizu Hideyuki,Hasegawa Masashi,Iyoda Masahiko
- Chemistry Letters, 2014
- 4,5-Dialkyl-1,2-bis(5-tropolonylethynyl)benzenes (5a and 5b) were synthesized, and dioctyl derivative 5a was converted into the corresponding trinuclear palladium(II) macrocycle 1a by reacting it with …
- NAID 130004677593
- Repression of Tropolone Production and Induction of a Burkholderia plantarii Pseudo-Biofilm by Carot-4-en-9, 10-diol, a Cell-to-Cell Signaling Disrupter Produced by Trichoderma virens
- Wang Mengcen,Hashimoto Makoto,Hashidoko Yasuyuki
- Plos one 8(11), 2013-11-04
- … Background: The tropolone-tolerant Trichoderma virens PS1-7 is a biocontrol agent against Burkholderia plantarii, causative of rice seedling blight. … plantarii leading to repression of tropolone production in a coculture system, bioassay-guided screening for active compounds from a 3-d culture of T. … As a result, carot-4-en-9,10-diol was identified and found to repress tropolone production of B. …
- NAID 120005365919
- ジエンの活性化を基盤とする触媒的 Diels-Alder 反応の開発と生理活性シクロヘキセンオキシド類およびカルバ糖類合成への応用
- 岡村 浩昭,岩川 哲夫,濱田 季之
- 有機合成化学協会誌 70(3), 227-239, 2012-03-01
- … In our continuous effort to develop the base-catalyzed DA, we have found that three different classes of compounds, 3-hydroxy-2-pyrone, 3-hydroxy-2-pyridone, and α-tropolone can be used as dienes suitable for the DA reaction. …
- NAID 10030481617
Related Links
- [Tropolone] [533-75-5] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日,つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては,お手数ですが営業部までお問い合わせください。
- Abstract Tropolone was shown to be bacteriostatic and bactericidal for a wide range of bacterial species. This antibacterial activity was quantitated using standard methods. Tropolone treatment of whole cells resulted in cell lysis ...
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