A Chemical Study of the Secretion of the Anal Glands of Mephitis Mephitiga (Common Skunk), With Remarks on the Physiological Properties of This Secretion

Aldrich, Thomas Bailey

doi:10.1084/jem.1.2.323

Cited by 25 publications

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“…Although the thioacetates tend to be less or nonodoriferous, their presence can contribute to the continual emanation of odors from affected humans, animals, and objects as the compounds undergo autohydrolysis or are subjected to microbial biotransformation into their thiol forms . The pungent odor of skunk thiols is highly persistent (e.g., compounds are oily and easily adhere to clothing, hair, and skin), and they are readily detectable by humans and other animals at low concentrations (e.g., the human nose can detect concentrations as low as ∼10 ppb) . Animals unfortunate enough to be directly exposed to skunk sprays can develop a variety of physical symptoms including ocular edema, conjunctivitis, drooling, and squinting.…”

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confidence: 99%

An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

Munteanu

King

et al. 2019

J. Nat. Prod.

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The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to “de-skunk” people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via SN2′-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.

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confidence: 99%