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(Z)-3-hexen-1-ol
''cis''-3-Hexen-1-ol, also known as (''Z'')-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. ''cis''-3-Hexen-1-ol is an important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes. Its esters are also important flavor and fragrance raw materials. The related aldehyde ''cis''-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated ''trans''-2-hexenal. This compound has been recognized as a semiochemical involved in mechanisms and behaviors of attraction in diverse animals such as insects and mammals. Human odor perception A pair of two single-nucleotide polymorphisms, both in the gene for the OR2J3 Olfactory receptor 2J3 is a protein that in humans is enc ...
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Ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the pseudoelement symbol for ethyl group, ethyl. Ethanol is a Volatility (chemistry), volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. As a psychoactive depressant, it is the active ingredient in alcoholic beverages, and the second most consumed drug globally behind caffeine. Ethanol is naturally produced by the fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration. Historically it was used as a general anesthetic, and has modern medical applications as an antiseptic, disinfectant, solvent for some medications, and antidote for methanol poisoning and ethylene glycol poisoning. It is used as a chemical solvent and in the Chemical synthesis, synthesis of orga ...
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Ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid ...
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OR2J3
Olfactory receptor 2J3 is a protein that in humans is encoded by the ''OR2J3'' gene. Olfactory receptors interact with odorant molecules in the nose, to initiate a neuronal response that triggers the perception of a smell. The olfactory receptor proteins are members of a large family of G-protein-coupled receptors (GPCR) arising from single coding-exon genes. Olfactory receptors share a 7-transmembrane domain structure with many neurotransmitter and hormone receptors and are responsible for the recognition and G protein-mediated transduction of odorant signals. The olfactory receptor gene family is the largest in the genome. The nomenclature assigned to the olfactory receptor genes and proteins for this organism is independent of other organisms. Genetic variation A pair of two single-nucleotide polymorphisms, both in the OR2J3 gene, strongly reduce sensitivity to the odorant cis-3-hexen-1-ol, which has a "cut grass" smell. Ligands * cis-3-Hexen-1-ol * Cinnamaldehyde See also ...
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Single-nucleotide Polymorphism
In genetics and bioinformatics, a single-nucleotide polymorphism (SNP ; plural SNPs ) is a germline substitution of a single nucleotide at a specific position in the genome. Although certain definitions require the substitution to be present in a sufficiently large fraction of the population (e.g. 1% or more), many publications do not apply such a frequency threshold. For example, a Guanine, G nucleotide present at a specific location in a reference genome may be replaced by an Adenine, A in a minority of individuals. The two possible nucleotide variations of this SNP – G or A – are called alleles. SNPs can help explain differences in susceptibility to a wide range of diseases across a population. For example, a common SNP in the Factor H, CFH gene is associated with increased risk of age-related macular degeneration. Differences in the severity of an illness or response to treatments may also be manifestations of genetic variations caused by SNPs. For example, two ...
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Mammals
A mammal () is a vertebrate animal of the class Mammalia (). Mammals are characterised by the presence of milk-producing mammary glands for feeding their young, a broad neocortex region of the brain, fur or hair, and three middle ear bones. These characteristics distinguish them from reptiles and birds, from which their ancestors diverged in the Carboniferous Period over 300 million years ago. Around 6,640 extant species of mammals have been described and divided into 27 orders. The study of mammals is called mammalogy. The largest orders of mammals, by number of species, are the rodents, bats, and eulipotyphlans (including hedgehogs, moles and shrews). The next three are the primates (including humans, monkeys and lemurs), the even-toed ungulates (including pigs, camels, and whales), and the Carnivora (including cats, dogs, and seals). Mammals are the only living members of Synapsida; this clade, together with Sauropsida (reptiles and ...
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Insects
Insects (from Latin ') are hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, thorax and abdomen), three pairs of jointed legs, compound eyes, and a pair of antennae. Insects are the most diverse group of animals, with more than a million described species; they represent more than half of all animal species. The insect nervous system consists of a brain and a ventral nerve cord. Most insects reproduce by laying eggs. Insects breathe air through a system of paired openings along their sides, connected to small tubes that take air directly to the tissues. The blood therefore does not carry oxygen; it is only partly contained in vessels, and some circulates in an open hemocoel. Insect vision is mainly through their compound eyes, with additional small ocelli. Many insects can hear, using tympanal organs, which may be on the legs or other parts of the b ...
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Semiochemical
A semiochemical, from the Greek wiktionary:σημεῖον, σημεῖον (''semeion''), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication can be divided into two broad classes: communication between individuals of the same species (intraspecific) or communication between different species (Interspecies communication, interspecific). It is usually used in the field of chemical ecology to encompass pheromones, allomones, kairomones, attractants and Animal repellent, repellents. Many insects, including Parasitoid#Parasitoidal insects, parasitic insects, use semiochemicals. Pheromones are intraspecific signals that aid in finding mates, food and habitat resources, warning of enemies, and avoiding competition. Interspecific signals known as allomones and kairomones have similar functions. In nature Pheromone A pheromone (from Greek ''phero'' "to bear" + ''hormone'' from Gree ...
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Trans-2-Hexenal
''trans''-2-Hexenal is an organic unsaturated aldehyde with a six-carbon chain. This clear, pale yellow liquid has a green, leafy, herbal fruit smell. It occurs naturally in a wide variety of plants, fruits, vegetables, and spices, and appears to be an important mediating and signalling chemical in plant-fungus and plant-insect interactions, such as the symbiosis between acacia ants and ''Acacias''. Occurrence This aldehyde is a commonly produced volatile organic compound (VOC) among the flowering plants. It is among the VOCs known as green leaf volatiles, as they are released following damage to the leaf, whether by crushing, herbivory, or bacterial or fungal infection. It is also found in other parts of the plant. For example, it was found to constitute 34% of the total VOCs from fresh strawberry fruits and 28% of VOCs from fresh tomato fruits. ''trans''-2-hexenal appears to be an airborne signalling chemical that can upregulate plant defenses, from leaf to leaf on th ...
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Conjugated System
In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Resonance (chemistry), conventionally represented as having alternating single and multiple covalent bond, bonds. Lone pairs, radical (chemistry), radicals or carbenium ions may be part of the system, which may be Cyclic molecule, cyclic, acyclic, Linear molecular geometry, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele (chemist), Johannes Thiele. Conjugation is the orbital overlap, overlap of one p-orbital with another across an adjacent Sigma bond, σ bond (in transition metals, d-orbitals can be involved). A conjugated system has a region of overlapping p-orbitals, bridging the interjacent locations that simple diagrams illustrate as not having a π bond. They allow a delocalization of pi el ...
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Isomerization
In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomerization. When the activation energy for the isomerization reaction is sufficiently small, both isomers can often be observed and the equilibrium ratio will shift in a temperature-dependent equilibrium with each other. Many values of the standard free energy difference, \Delta G^\circ, have been calculated, with good agreement between observed and calculated data. Examples and applications Alkanes Skeletal isomerization occurs in the cracking process, used in the petrochemical industry to convert straight chain alkanes to isoparaffins as exemplified in the conversion of normal octane to 2,5-dimethylhexane (an "isoparaffin"): : Fuels containing branched hydrocarbons are favored for internal combustion engines for their higher octan ...
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Cis-3-Hexenal
''cis''-3-Hexenal, also known as (''Z'')-3-hexenal and leaf aldehyde, is an organic compound with the formula CH3CH2CH=CHCH2CHO. It is classified as an unsaturated aldehyde. It is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves. Occurrence It is one of the major volatile compounds in ripe tomatoes, although it tends to isomerize into the conjugated ''trans''-2-hexenal. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. It is also a pheromone in many insect species. See also * ''cis''-3-Hexen-1-ol has a similar but weaker odor and is used in flavors and perfumes. * 1-Hexanol, another volatile organic compound Volatile organic compounds (VOCs) are organic compounds that have a high vapor pressure at room temperature. They are common and exist in a variety of settings and products, not limited to Indoor mold, house mold, Upholstery, upholstered furnitur ..., also considered ...
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Aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Structure and bonding Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The bond length is about 120–122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are solubl ...
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