Cis-3-Hexen-1-ol

Cis-3-Hexen-1-ol, also known as leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is a volatile organic compound (VOC) that plays a significant role in the aroma of plants and is widely used in flavors and fragrances to impart a fresh green note.

Chemistry

Cis-3-Hexen-1-ol belongs to the family of alcohols, specifically the hexenols, which are alcohols containing a 6-carbon chain with one double bond and an alcohol functional group. The "cis" designation indicates the configuration of the molecule around the double bond; in cis-3-Hexen-1-ol, the hydrogen atoms adjacent to the double bond are on the same side, which significantly influences its aroma characteristics compared to its trans counterpart.

The chemical formula for cis-3-Hexen-1-ol is C6H12O, and it is often represented by the molecular formula CH3(CH2)2CH=CHCH2OH, highlighting its structure and functional groups.

Production

Cis-3-Hexen-1-ol is produced both synthetically and naturally. In nature, it is formed through the lipoxygenase pathway from linolenic acid in green plants. The synthetic production involves several chemical reactions, starting from hexanal or other suitable precursors, to introduce the alcohol functional group and establish the correct cis configuration.

Applications

The primary use of cis-3-Hexen-1-ol is in the flavor and fragrance industry. Its distinctive green, grassy odor makes it a valuable component in perfumes, air fresheners, and household products, as well as in flavorings for food and beverages to impart a fresh, green note.

In Perfumery

In perfumery, cis-3-Hexen-1-ol is used to create leafy, green accords, often in combination with other floral, fruity, or woody notes to mimic the smell of a garden or forest. It is appreciated for its ability to add freshness and lift to fragrances.

In Flavors

In the flavor industry, cis-3-Hexen-1-ol is added to various food products, including beverages, candies, and dairy products, to impart a fresh green taste that resembles the flavor of fresh fruits and vegetables.

Safety and Regulations

As with many flavor and fragrance ingredients, the safety of cis-3-Hexen-1-ol is evaluated by regulatory bodies such as the International Fragrance Association (IFRA) and the Flavor and Extract Manufacturers Association (FEMA). These organizations set guidelines for the safe use of cis-3-Hexen-1-ol in various products to ensure consumer safety.

Environmental Impact

Being a volatile organic compound, cis-3-Hexen-1-ol can contribute to the formation of photochemical smog when released into the atmosphere. However, its impact is minimal compared to other VOCs due to its relatively low volatility and concentration in the environment.

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  Cis-3-Hexen-1-ol chemical structure

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  Cis-3-Hexen-1-ol 3D model