Cis-3-Hexenal: Difference between revisions

Latest revision as of 11:01, 15 February 2025

Overview[edit]

Cis-3-Hexenal is a volatile organic compound that is commonly associated with the aroma of freshly cut grass. It is a type of aldehyde and is part of the green leaf volatiles (GLVs) group, which are emitted by plants when they are damaged. This compound plays a significant role in plant defense mechanisms and has applications in the flavor and fragrance industries.

Chemical Structure[edit]

Cis-3-Hexenal is an unsaturated aldehyde with the chemical formula C₆H₁₀O. It features a double bond in the cis configuration, which contributes to its distinct scent. The presence of the aldehyde group makes it reactive and an important intermediate in various biochemical pathways.

Biosynthesis[edit]

Cis-3-Hexenal is synthesized in plants through the lipoxygenase pathway. This pathway involves the oxidation of linolenic acid to produce hydroperoxides, which are then cleaved by hydroperoxide lyase to form cis-3-hexenal. This process is part of the plant's response to mechanical damage or herbivore attack, leading to the release of GLVs that can deter herbivores or attract predators of the herbivores.

Role in Plant Defense[edit]

The release of cis-3-hexenal and other GLVs serves as a signaling mechanism in plants. These compounds can act as direct deterrents to herbivores or as indirect signals that attract natural enemies of the herbivores, such as parasitoid wasps. Additionally, GLVs can prime neighboring plants to enhance their own defensive responses, a phenomenon known as "priming".

Applications[edit]

Cis-3-Hexenal is widely used in the flavor and fragrance industries due to its fresh, green aroma. It is a key component in the formulation of perfumes and is also used to impart a natural, fresh scent to various consumer products. In the food industry, it is used to enhance the flavor of products such as fruit juices and confectionery.

Related Compounds[edit]

Cis-3-Hexenal is closely related to other GLVs, such as cis-3-hexenol and trans-2-hexenal, which also contribute to the characteristic "green" aroma. These compounds share similar biosynthetic pathways and functions in plant defense.

Related Pages[edit]

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-'''Cis-3-Hexenal''', also known as (Z)-3-hexenal and leaf aldehyde, is an [[organic compound]] with the formula C<sub>6</sub>H<sub>10</sub>O. It is a colorless liquid that is an important aroma compound found in nature. Cis-3-Hexenal has a distinctive fresh, green, grassy odor and is a significant contributor to the aroma of green leaves, unripe fruits, and at certain concentrations, it imparts a pleasant odor reminiscent of freshly cut grass. Due to its potent odor, it is used in very low concentrations in perfumery and flavors.
+{{DISPLAYTITLE:Cis-3-Hexenal}}
-==Structure and Properties==
+== Overview ==
-Cis-3-Hexenal is an [[aldehyde]] and a [[monounsaturated compound]], with the double bond in the cis configuration, which significantly influences its aroma and chemical properties. The molecule consists of a six-carbon chain with an aldehyde group at one end. The cis configuration of the double bond at the third carbon atom is crucial for its characteristic odor.
+'''Cis-3-Hexenal''' is a volatile organic compound that is commonly associated with the aroma of freshly cut grass. It is a type of [[aldehyde]] and is part of the [[green leaf volatiles]] (GLVs) group, which are emitted by plants when they are damaged. This compound plays a significant role in plant defense mechanisms and has applications in the flavor and fragrance industries.
-==Biosynthesis==
+== Chemical Structure ==
-In plants, cis-3-Hexenal is formed from linolenic acid via the [[lipoxygenase]] pathway. The enzyme lipoxygenase adds oxygen to linolenic acid, which is then converted by other enzymes into cis-3-Hexenal. This compound is often released when plant tissues are damaged, as part of the plant's defense mechanism against herbivores.
+[[File:O2aseLyaseFatty.png|thumb|right|Chemical structure of Cis-3-Hexenal]]
+Cis-3-Hexenal is an unsaturated aldehyde with the chemical formula C<sub>6</sub>H<sub>10</sub>O. It features a double bond in the cis configuration, which contributes to its distinct scent. The presence of the aldehyde group makes it reactive and an important intermediate in various biochemical pathways.
-==Occurrence==
+== Biosynthesis ==
-Cis-3-Hexenal is widely distributed in nature. It is found in the volatile components of many fruits and vegetables, including tomatoes, apples, and green peppers. It is also a significant component of the aroma of freshly cut grass and leaves. The compound plays a crucial role in the flavor profile of many fresh foods and is valued for its contribution to the "green" notes of their aroma.
+Cis-3-Hexenal is synthesized in plants through the [[lipoxygenase pathway]]. This pathway involves the oxidation of [[linolenic acid]] to produce hydroperoxides, which are then cleaved by [[hydroperoxide lyase]] to form cis-3-hexenal. This process is part of the plant's response to mechanical damage or herbivore attack, leading to the release of GLVs that can deter herbivores or attract predators of the herbivores.
-==Uses==
+== Role in Plant Defense ==
-Due to its distinctive smell, cis-3-Hexenal is used in the flavor and fragrance industry. It is added to food products to impart a fresh, green aroma and is used in perfumery to create natural green, grassy scents. However, due to its high volatility and reactivity, its use must be carefully controlled to avoid undesirable off-flavors and aromas.
+The release of cis-3-hexenal and other GLVs serves as a signaling mechanism in plants. These compounds can act as direct deterrents to herbivores or as indirect signals that attract natural enemies of the herbivores, such as [[parasitoid wasps]]. Additionally, GLVs can prime neighboring plants to enhance their own defensive responses, a phenomenon known as "[[priming]]".
-==Safety and Toxicology==
+== Applications ==
-Cis-3-Hexenal is generally considered safe for use in flavors and fragrances. However, like many aldehydes, it can be irritating to the skin and eyes in high concentrations. Proper handling and dilution are necessary to mitigate these effects.
+Cis-3-Hexenal is widely used in the flavor and fragrance industries due to its fresh, green aroma. It is a key component in the formulation of perfumes and is also used to impart a natural, fresh scent to various consumer products. In the food industry, it is used to enhance the flavor of products such as fruit juices and confectionery.
-[[Category:Organic compounds]]
+== Related Compounds ==
-[[Category:Aldehydes]]
+Cis-3-Hexenal is closely related to other GLVs, such as [[cis-3-hexenol]] and [[trans-2-hexenal]], which also contribute to the characteristic "green" aroma. These compounds share similar biosynthetic pathways and functions in plant defense.
-[[Category:Flavor chemistry]]
-[[Category:Aroma compounds]]
-{{Chem-stub}}
+== Related Pages ==
+* [[Aldehyde]]
+* [[Green leaf volatiles]]
+* [[Lipoxygenase pathway]]
+* [[Plant defense mechanisms]]
+[[Category:Volatile organic compounds]]
+[[Category:Plant physiology]]
+[[Category:Flavors]]