June 05, 2023
My reactivity makes me useful but also dangerous.
What molecule am I?
Image of Glutaraldehyde 3D Image of Glutaraldehyde

Glutaraldehyde is a dialdehyde and a reduced form of the corresponding diacid, glutaric acid. It was mentioned (as “trimethylene aldehyde”) 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 (“trimethylene carbinol”).

Other ways to prepare glutaraldehyde include acidification of 2-methoxy- or 2-ethoxy-3,4-dihydro-2H-pyran and tungstic acid–catalyzed 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’s many uses include sterilizing medical equipment, tanning leather, cross-linking polymers, and acting as a fixative in biochemical procedures. It has even been tried as an ingredient in hair treatments, such as “permanent” waves.

Additional information about glutaraldehyde applications can be found on the ScienceDirect information page.

Glutaraldehyde hazard information*

Hazard class**GHS code and hazard statement
Acute toxicity, oral, category 4H302—Harmful if swallowedChemical Safety Warning
Skin corrosion/irritation, category 1BH314—Causes severe skin burns and eye damageChemical Safety Warning
Skin sensitization, category 1H317—May cause an allergic skin reactionChemical Safety Warning
Serious eye damage/eye irritation, category 1H318—Causes serious eye damageChemical Safety Warning
Acute toxicity, inhalation, category 3H331—Toxic if inhaledChemical Safety Warning
Respiratory sensitization, category 1H334—May cause allergy or asthma symptoms or breathing difficulties if inhaledChemical Safety Warning
Specific target organ toxicity, single exposure, respiratory tract irritation, category 3H335—May cause respiratory irritationChemical Safety Warning
Short-term (acute) aquatic hazard, category 1H400—Very toxic to aquatic lifeChemical Safety Warning
Long-term (acute) aquatic hazard, category 1H410—Very toxic to aquatic life with long-lasting effectsChemical Safety Warning

*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. Explanation of pictograms.

Molecules from the journals

The makaluvamines are natural alkaloids with pyrroloiminoquinone structures. Makaluvamine A1 was isolated from the Fijian sea sponge 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) isolated makaluvamine K2 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 total synthesis of both compounds with a Larock indole synthesis as the first step in each sequence.

Illisimonin A4 is a natural caged sesquiterpenoid with an intricate tricyclo[,6]decane skeleton. It was isolated in 2017 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 total asymmetric synthesis of illisimonin A 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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 fast facts

CAS Reg. No.111-30-8
SciFinder nomenclaturePentanedial
Empirical formulaC5H8O2
Molar mass100.12
AppearanceColorless to light yellow viscous liquid
Boiling point187–189 °C
Water solubilityMiscible
Chemical Abstract Service - a division of ACS

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