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Merck
CN

15702

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:
533-75-5
Molecular Weight:
122.12
EC Number:
208-577-2
UNSPSC Code:
12352200
NACRES:
NA.21
Beilstein/REAXYS Number:
1904978
MDL number:
MFCD00004158
Assay:
≥98.0% (GC)
Form:
solid

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Quality Level

400

InChI

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

InChI key

MDYOLVRUBBJPFM-UHFFFAOYSA-N

SMILES string

OC1=CC=CC=CC1=O

assay

≥98.0% (GC)

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.)

suitability

suitable for manufacturing use

storage temp.

2-8°C

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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

signalword

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

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC1973
BCCC1972
BCCC1971
BCCC1895
BCCB5729

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Jessica L Fullagar et al.
Chemical communications (Cambridge, England), 49(31), 3197-3199 (2013-03-14)
Tropolone emerged from the screening of a chelator fragment library (CFL) as an inhibitor of the Zn(2+)-dependent virulence factor, Pseudomonas aeruginosa elastase (LasB). Based on this initial hit, a series of substituted tropolone-based LasB inhibitors was prepared, and a compound
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
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
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
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