What molecule am I?
2-Deoxy-2-fluoro-D-glucose1, a fluorinated derivative of glucose, in 1969 by Josef Pac谩k*, Zden臎k To膷ik, and Miloslav 膶ern媒 at Charles University (Prague) in a four-step sequence beginning with 1,6-anhydro-4-O-benzyl-2-O-(p-迟辞濒测濒蝉耻濒蹿辞苍测濒)-尾-D-glucopyranose2, which they had prepared the previous year. In 1993, Stephen G. Withers and co-workers at the University of British Columbia (Vancouver) by treating a peracetate derivative of 2-deoxy-D-glucose with acetyl hypofluorite3.
But the real story here is the radioactive form of 2-deoxy-2-fluoro-D-glucose, 2-deoxy-2-(fluoro-18F)-D-glucose. The 18fluorine isotope is a positron emitter that has become useful in medical imaging via positron emission tomography (PET) as a marker for glucose in the body.
2-Deoxy-2-(fluoro-18F)-D-glucose was synthesized in 1978 by Tatsuo Ido, Alfred P. Wolf, and co-workers at the Brookhaven National Laboratory (Upton, NY). They used a method different from that of Pac谩k et al: 3,4,6-Tri-O-acetyl-D-glucal4 was , followed by hydrolysis to give the desired labeled compound and the equivalent mannose derivative. For good measure, the authors also prepared a 14C-labeled version of 2-deoxy-2-fluoro-D-glucose.
The application of 2-deoxy-2-(fluoro-18F)-D-glucose for glucose tracing with PET is especially useful in tumor imaging. The technique, in combination with computed tomography (CT) scanning, is also used for evaluating glucose metabolism in the heart and brain. These, along with other applications, are described in the more than 45,000 citations for the molecule in Chemical Abstract Service鈥檚 .
1. CAS Reg. No. 29702-43-0.
2. CAS Reg. No. 20183-65-7.
3. CAS Reg. No. 78948-09-1.
4. CAS Reg. No. 2873-29-2.
2-Deoxy-2-fluoro-D-glucose hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Skin corrosion/irritation, category 2 | H315鈥擟auses skin irritation |  |
| Serious eye damage/eye irritation, category 2A | H319鈥擟auses serious eye irritation | |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
*Hazard information unavailable for 2-deoxy-2-(fluoro-18F)-D-glucose does not account for hazards associated with radioactivity.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.听.
Molecule from the Journals: Hazard Alert
N-Bromosuccinimide1 (NBS) is a valuable reagent in organic chemistry. It is primarily used in electrophilic and radical bromination reactions. Its use was established in an extensive 1942 article titled 鈥溾� by Karl Ziegler and co-workers at the University of Halle鈥揝aale (Germany; now Martin Luther University Halle鈥揥ittenberg). Ziegler and Italian chemical engineer Giulio Natta won the 1963 Nobel Prize in Chemistry for their pioneering work in polymers.
Since its introduction, NBS has been used widely and safely. But last month, Elsa M. Gon莽alves and colleagues at Hovione FarmaCiencia (Lisbon) reported that when a 22% solution of NBS in N,N-dimethylformamide2 (DMF) was heated to 80 掳C, it to give off a gas consisting of decomposition products of both compounds. After an extensive investigation of the decomposition reaction, the authors concluded that the maximum safe working temperature for solutions of NBS in DMF under industrial conditions is 32 掳C.
1. CAS Reg. No. 128-08-5.
2. CAS Reg. No. 68-12-2.
Molecule from the Journals: Hazard Alert
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2-Deoxy-2-(fluoro-18F)-D-glucose fast facts
| CAS Reg. No. | 63503-12-8 |
| SciFinder nomenclature | D-Glucose, 2-deoxy-2-(fluoro-18F)- |
| Empirical formula | C6H1118FO5 |
| Molar mass | 181.15 g/mol |
| Appearance | White crystals or powder |
| Melting point | 174鈥�176 掳Ca |
| Water solubility | 10 g/La |
a. Data for 2-deoxy-2-fluoro-D-glucose.
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