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Tropolon

Tropolon[1]
Skeletna formula tropolon
Skeletna formula tropolon
Space-filling model of tropolone
Space-filling model of tropolone
Imena
IUPAC ime
2-hidroksi-2,4,6-cikloheptatrien-1-on
Druga imena
2-hidroksitropon; Purpurokatehol
Identifikatorji
3D model (JSmol)
ChEMBL
ChemSpider
EC število
  • 208-577-2
KEGG
MeSH D014334
UNII
  • InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
    Key: MDYOLVRUBBJPFM-UHFFFAOYSA-N
  • InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
    Key: MDYOLVRUBBJPFM-UHFFFAOYAW
  • C1=CC=C(C(=O)C=C1)O
Lastnosti
C7H6O2
Molska masa 122,12 g/mol
Tališče 50–52 °C
Vrelišče 80–84 °C (0,1 mmHg)
Kislost (pKa) 6.89 ( -0.5 za konjugirane kisline)
Nevarnosti
S-stavki (zastarelo) S22 Predloga:S24/25
Plamenišče 112 °C (234 °F; 385 K)
Sorodne snovi
Sorodne snovi Hinokitiol (4-izopropil-tropolon)
Če ni navedeno drugače, podatki veljajo za material v standardnem stanju pri 25 °C, 100 kPa).
Sklici infopolja

Tropolon je hidroksiderivat tropona. Obstajajo trije tropoloni, odvisno od mesta vezave hidroksilne skupine.

Sinteza tropolona poteka na dva načina: 1. z bromiranjem 1,2-cikloheptandiona (uporabimo N-Bromosukcinimid in kasnejšo dehidrohalogenacijo pri zvišani temperaturi; 2. z akiloinsko kondenzacijo etilestra pimelične kisline in akiloina ter kasnejšo oksidacijo z bromom.

Sinteza tropolona
Sinteza tropolona

α-tropolon je inhibitor grozdne polifenol oksidaze.[2][3]

Sklici

  1. Tropolone at Sigma-Aldrich
  2. 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
  3. Chedgy Russell (2010). Secondary metabolites of Western red cedar (Thuja plicata): their biotechnological applications and role in conferring natural durability. LAP Lambert Academic Publishing. ISBN 978-3-8383-4661-8.

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