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93555

Sigma-Aldrich

Tropolone

purum, ≥98.0% (GC)

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
Beilstein/REAXYS Number:
1904978
EC Number:
208-577-2
MDL number:
MFCD00004158
UNSPSC Code:
12352100
PubChem Substance ID:
329770251
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥98.0% (GC)

form

crystals

bp

80-84 °C/0.1 mmHg (lit.)

mp

50-52 °C (lit.)
50-52 °C

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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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_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBN1113V
BCBP5471V
BCBJ1085V
BCBH6541V
BCBH4628V

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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
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
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
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