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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

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storage temp.

2-8°C

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.)

mp

50-52 °C (lit.)

suitability

suitable for manufacturing use

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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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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
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
Mohammad R Seyedsayamdost et al.
Journal of the American Chemical Society, 133(45), 18343-18349 (2011-09-21)
Marine bacteria and microalgae engage in dynamic symbioses mediated by small molecules. A recent study of Phaeobacter gallaeciensis, a member of the large roseobacter clade of α-proteobacteria, and Emiliania huxleyi, a prominent member of the microphytoplankton found in large algal
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
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