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Tropolone

Synonym(s):

2-Hydroxy-2,4,6-cycloheptatrien-1-one

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About This Item

Empirical Formula (Hill Notation):
C7H6O2
CAS Number:
Molecular Weight:
122.12
Beilstein/REAXYS Number:
1904978
EC Number:
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21

assay

≥98.0% (GC)

Quality Level

form

solid

impurities

≤20 mg/kg heavy metals
≤3880 mg/kg residual solvents (cyclohexane) (GLC-HS)
≤5000 mg/kg residual solvents (pentane, MTBE) (GLC-HS)
≤890 mg/kg residual solvents (toluene) (GLC-HS)

bp

80-84 °C/0.1 mmHg (lit.)

mp

50-52 °C (lit.)

suitability

suitable for manufacturing use

storage temp.

2-8°C

SMILES string

OC1=CC=CC=CC1=O

InChI

1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

InChI key

MDYOLVRUBBJPFM-UHFFFAOYSA-N

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Analysis Note

remarks on GC:
acetic acid ≤5000 mg/kg; dichloroacetic acid: determine

solubility
0.25g in 5 ml ethanol, clear to very faintly turbid

solubility color:
colorless to very dark yellow and colorless to very dark greenish yellow and colorless to very dark brownish yellow and colorless to very dark orange

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Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup


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Tomasz Borowski et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 17(6), 881-890 (2012-05-25)
6-Hydroxymethyl-6-methylcyclohexa-2,4-dienone is a mechanistic probe which when incubated with an extradiol dioxygenase yields a 2-tropolone product. This observation was originally interpreted as evidence supporting a direct heterolytic 1,2-alkenyl migration mechanism for a ring expansion reaction catalyzed by this class of
Eric Sabondjian et al.
Contrast media & molecular imaging, 7(1), 76-84 (2012-02-22)
A challenge with cardiac cell therapy is determining the location of cells relative to infarct tissue. As cells are viable following ¹¹¹In-labeling, and first-pass CT imaging can identify regions of myocardial infarction, we evaluated the feasibility of a SPECT/CT system
Christine Meck et al.
Organic letters, 14(23), 5988-5991 (2012-11-22)
α-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that α-hydroxytropolones
Jack Davison et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(20), 7642-7647 (2012-04-18)
A gene cluster encoding the biosynthesis of the fungal tropolone stipitatic acid was discovered in Talaromyces stipitatus (Penicillium stipitatum) and investigated by targeted gene knockout. A minimum of three genes are required to form the tropolone nucleus: tropA encodes a
Mengcen Wang et al.
Applied and environmental microbiology, 79(6), 1906-1914 (2013-01-15)
To screen biocontrol agents against Burkholderia plantarii, the causative agent of rice seedling blight, we employed catechol, an analog of the virulence factor tropolone, to obtain chemical stress-resistant microorganisms. The fungal isolate PS1-7, identified as a strain of Trichoderma virens

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