Dihydrocapsaicin

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (pungent (hot) components of green and red pepper). Like capsaicin, it is a vanilloid, and also has the vanilloid name N-vanillylnonanamide. It is a secondary metabolite of chili peppers, which contributes to the overall heat sensation when consumed.

Chemical Structure and Properties

Dihydrocapsaicin has the chemical formula C18H29NO3 and a molecular weight of 307.43 g/mol. It is structurally similar to capsaicin, but has a slightly different chemical structure. The molecule consists of a vanillyl group, a nonanoyl chain, and an amide functional group. The vanillyl group is derived from vanillin, a component of vanilla beans, and the nonanoyl chain is a type of fatty acid. The amide functional group connects the two other groups.

Occurrence and Extraction

Dihydrocapsaicin is found in the Capsicum genus, which includes chili peppers. It is typically present in lower quantities than capsaicin, but contributes significantly to the overall heat of the pepper. The compound can be extracted from chili peppers using organic solvents, followed by purification processes such as chromatography.

Uses

Dihydrocapsaicin is used in the food industry as a flavor additive due to its heat-producing properties. It is also used in the pharmaceutical industry for its analgesic properties. It is an active ingredient in some topical pain relief creams, where it works by depleting a neurotransmitter called Substance P that transmits pain signals to the brain.

Safety and Toxicity

Like other capsaicinoids, dihydrocapsaicin can cause a burning sensation when it comes into contact with mucous membranes. It can also cause skin irritation in some individuals. Ingestion of large amounts can cause gastrointestinal discomfort. The LD50 (lethal dose for 50% of the population) for dihydrocapsaicin in mice is 118.8mg/kg.

See Also

• Capsaicin
• Capsicum
• Vanilloids
• Scoville Scale