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Glutaraldehyde is a dialdehyde and a reduced form of the corresponding diacid, glutaric acid. It was mentioned (as 鈥渢rimethylene aldehyde鈥�) in the chemical literature as early as 1908, when Russian chemists N. J. Demjanow* and K. Fortunatow synthesized it via the chromic oxide oxidation of 1,5-pentanediol (鈥渢rimethylene carbinol鈥�).
Other ways to prepare glutaraldehyde include acidification of 2-methoxy- or 2-ethoxy-3,4-dihydro-2H-pyran and tungstic acid鈥揷atalyzed hydrogen peroxide oxidation of cyclopentene.
Because of its highly reactive aldehyde groups, glutaraldehyde is too unstable to store in its pure form. The article of commerce is usually a 25% or 50% aqueous solution; but it is also sold in methanol solution. As the hazard information table shows, it is toxic and must be handled carefully.
Glutaraldehyde鈥檚 many uses include sterilizing medical equipment, tanning leather, cross-linking polymers, and acting as a fixative in biochemical procedures. It听has even been tried as an ingredient in hair treatments, such as 鈥減ermanent鈥� waves.
Additional information about glutaraldehyde applications can be found on the .
Glutaraldehyde hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed |  |
| Skin corrosion/irritation, category 1B | H314鈥擟auses severe skin burns and eye damage |  |
| Skin sensitization, category 1 | H317鈥擬ay cause an allergic skin reaction | |
| Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage | |
| Acute toxicity, inhalation, category 3 | H331鈥擳oxic if inhaled |  |
| Respiratory sensitization, category 1 | H334鈥擬ay cause allergy or asthma symptoms or breathing difficulties if inhaled |  |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
| Short-term (acute) aquatic hazard, category 1 | H400鈥擵ery toxic to aquatic life |  |
| Long-term (acute) aquatic hazard, category 1 | H410鈥擵ery toxic to aquatic life with long-lasting effects | |
*Data for 50% aqueous solution. This information is from one safety data sheet; some other data sheets contain conflicting information.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.听.
Molecules from the journals
The makaluvamines are natural alkaloids with pyrroloiminoquinone structures. Makaluvamine A1 was Zyzzya fuliginosa in 1993 by Chris M. Ireland and coauthors at the University of Utah (Salt Lake City) and American Cyanamid (Pearl River, NY). Two years later, D. John Faulkner and co-workers at the Scripps Institution of Oceanography (La Jolla, CA) from the same sponge species.
Both alkaloids show inhibitory activity toward topoisomerase II3 and cytotoxic activity against HCT-116 human colon cancer cells. In March, John L. Wood and colleagues at Baylor University (Waco, TX) reported the with a Larock indole synthesis as the first step in each sequence.
Illisimonin A4 is a natural caged sesquiterpenoid with an intricate tricyclo[5.2.1.01,6]decane skeleton. It was from the fruit of the southeast Asian shrub Illicium simonsii by Jing Qu, Shan Yu, and co-workers at the Chinese Academy of Medical Sciences and Peking Union Medical College (both in Beijing).
Substances with this structure are known for their high oxidation levels and their neurotrophic (neuron-growing) properties. In March, Markus Kalesse and colleagues at the University of Hanover (Germany) reported a 21-step from a previously synthesized propargylic alcohol derivative.
1. CAS Reg. No. 146555-78-4.
2. CAS Reg. No. 174232-36-1.
3. An enzyme that simultaneously cuts both strands of DNA helices and is a frequent chemotherapy target; CAS Reg. No. 142805-56-9.
4. CAS Reg. No. 2162197-76-2.
Molecules from the Journals
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Glutaraldehyde
听fast facts
| CAS Reg. No. | 111-30-8 |
| SciFinder nomenclature | Pentanedial |
| Empirical formula | C5H8O2 |
| Molar mass | 100.12 |
| Appearance | Colorless to light yellow viscous liquid |
| Boiling point | 187鈥�189 掳C |
| Water solubility | Miscible |
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