Names | |
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Preferred IUPAC name (1E)-1-Nitropentadec-1-ene | |
Other names (E)-1-nitropentadec-1-ene | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C15H29NO2 | |
Molar mass | 255.402 g·mol−1 |
log P | 6.911 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Nitropentadecene, or more precisely (E)-1-nitropentadec-1-ene, is a highly toxic unsaturated nitroalkene, the only aliphatic nitro compound known to be synthesized by insects.[ citation needed ] It is produced by termite soldiers of genus Prorhinotermes (Isoptera, Rhinotermitidae) as a defensive chemical. [1] [2] Nitropentadecene is biosynthesized and stored in one of the exocrine glands, a frontal gland, of termite soldiers, and it is released upon attack of enemy.
Termites are a group of detritophagous eusocial insects which consume a wide variety of decaying plant material, generally in the form of wood, leaf litter, and soil humus. They are distinguished by their moniliform antennae and the soft-bodied and often unpigmented worker caste for which they have been commonly termed "white ants"; however, they are not ants, to which they are only distantly related. About 2,972 extant species are currently described, 2,105 of which are members of the family Termitidae.
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.
Autothysis or suicidal altruism is the process where an animal destroys itself via an internal rupturing or explosion of an organ which ruptures the skin. The term was proposed by Ulrich Maschwitz and Eleonore Maschwitz in 1974 to describe the defensive mechanism of Colobopsis saundersi, a species of ant. It is caused by a contraction of muscles around a large gland that leads to the breaking of the gland wall. Some termites release a sticky secretion by rupturing a gland near the skin of their neck, producing a tar effect in defense against ants.
The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-nitro alcohols. This type of reaction is also referred to as a nitroaldol reaction. It is nearly analogous to the aldol reaction that had been discovered 23 years prior that couples two carbonyl compounds to form β-hydroxy carbonyl compounds known as "aldols". The Henry reaction is a useful technique in the area of organic chemistry due to the synthetic utility of its corresponding products, as they can be easily converted to other useful synthetic intermediates. These conversions include subsequent dehydration to yield nitroalkenes, oxidation of the secondary alcohol to yield α-nitro ketones, or reduction of the nitro group to yield β-amino alcohols.
Blattodea is an order of insects that contains cockroaches and termites. Formerly, termites were considered a separate order, Isoptera, but genetic and molecular evidence suggests they evolved from within the cockroach lineage, cladistically making them cockroaches as well. The Blattodea and the mantis are now all considered part of the superorder Dictyoptera. Blattodea includes approximately 4,400 species of cockroach in almost 500 genera, and about 3,000 species of termite in around 300 genera.
The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.
Reticulitermes flavipes, the eastern subterranean termite, is the most common termite found in North America. These termites are the most economically important wood destroying insects in the United States and are classified as pests. They feed on cellulose material such as the structural wood in buildings, wooden fixtures, paper, books, and cotton. A mature colony can range from 20,000 workers to as high as 5 million workers and the primary queen of the colony lays 5,000 to 10,000 eggs per year to add to this total.
Colobopsis saundersi, also called the Malaysian exploding ant, is a species of ant found in Malaysia and Brunei, belonging to the genus Colobopsis. A worker can explode suicidally and aggressively as an ultimate act of defense, an ability it has in common with several other species in this genus and a few other insects. The ant has an enormously enlarged mandibular gland, many times the size of other ants, which produces adhesive secretions for defense. According to a 2018 study, this species forms a species complex and is probably related to C. explodens, which is part of the C. cylindrica group.
The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.
Globitermes sulphureus is a species of termite that is very common in central and southern Vietnam and also present in other areas of South East Asia, including Cambodia, Thailand, and Peninsular Malaysia. They live in nests made of earth that can be up to 1.5 m tall and can contain tens of thousands of individuals. Between five and 10 per cent of the population are soldier termites which can be recognised by their yellow abdomen and two large, curved mandibles. The termites use autothysis as a defense mechanism.
The Barton–Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanide under basic conditions. It is named after Derek Barton and Samir Zard who first reported it in 1985.
Insects have a wide variety of predators, including birds, reptiles, amphibians, mammals, carnivorous plants, and other arthropods. The great majority (80–99.99%) of individuals born do not survive to reproductive age, with perhaps 50% of this mortality rate attributed to predation. In order to deal with this ongoing escapist battle, insects have evolved a wide range of defense mechanisms. The only restraint on these adaptations is that their cost, in terms of time and energy, does not exceed the benefit that they provide to the organism. The further that a feature tips the balance towards beneficial, the more likely that selection will act upon the trait, passing it down to further generations. The opposite also holds true; defenses that are too costly will have a little chance of being passed down. Examples of defenses that have withstood the test of time include hiding, escape by flight or running, and firmly holding ground to fight as well as producing chemicals and social structures that help prevent predation.
Trail pheromones are semiochemicals secreted from the body of an individual to affect the behavior of another individual receiving it. Trail pheromones often serve as a multi purpose chemical secretion that leads members of its own species towards a food source, while representing a territorial mark in the form of an allomone to organisms outside of their species. Specifically, trail pheromones are often incorporated with secretions of more than one exocrine gland to produce a higher degree of specificity. Considered one of the primary chemical signaling methods in which many social insects depend on, trail pheromone deposition can be considered one of the main facets to explain the success of social insect communication today. Many species of ants, including those in the genus Crematogaster use trail pheromones.
The fontanellar gun is a termite defense mechanism in the form of a horn-like frontal projection (nasus) on the head of the soldier caste which is capable of expelling chemical weaponry at a distance, a trait exclusive to the subfamily Nasutitermitinae. It is primarily used to ward off predators such as ants.
Nitroethylene (also known as nitroethene) is a liquid organic compound with the formula C2H3NO2. It is the simplest nitroalkene, which are unsaturated carbon chains with at least one double bond and a NO2 functional group. Nitroethylene serves as a useful intermediate in the production of various other chemicals.
A nitroalkene, or nitro olefin, is a functional group combining the functionality of its constituent parts, an alkene and nitro group, while displaying its own chemical properties through alkene activation, making the functional group useful in specialty reactions such as the Michael reaction or Diels-Alder additions.
Phagomimicry is a defensive behaviour of sea hares, in which the animal ejects a mixture of chemicals, which mimic food, and overwhelm the senses of their predator, giving the sea hare a chance to escape. The typical defence response of the sea hare to a predator is to release two chemicals - ink from the ink gland and opaline from the opaline gland. While ink creates a dark, diffuse cloud in the water which disrupts the sensory perception of the predator by acting as a smokescreen and as a decoy, the opaline, which affects the senses dealing with feeding, causes the predator to instinctively attack the cloud of chemicals as if it were indeed food. This ink is able to mimic food by having a high concentration of amino acids and other compounds that are normally found in food, and the attack behaviour of the predator allows the sea-hares the opportunity to escape.
Macrotermes carbonarius, also known as Kongkiak in Malay, is a large black species of fungus-growing termite in the genus Macrotermes. It is one of the most conspicuous species of Macrotermes found in the Indomalayan tropics, forming large foraging trails in the open that can extend several metres in distance. M. carbonarius is a highly aggressive species with the soldiers possessing large curving mandibles that easily break skin. It is found in Cambodia, Malaysia, Myanmar, Singapore, Thailand and Vietnam.
The nitro-Mannich reaction is the nucleophilic addition of a nitroalkane to an imine, resulting in the formation of a beta-nitroamine. With the reaction involving the addition of an acidic carbon nucleophile to a carbon-heteroatom double bond, the nitro-Mannich reaction is related to some of the most fundamental carbon-carbon bond forming reactions in organic chemistry, including the aldol reaction, Henry reaction and Mannich reaction.
The Syntermitinae, also known as the mandibulate nasutes, is a Neotropical subfamily of higher termites represented by 21 genera and 103 species. The soldier caste of members of this subfamily have a conspicuous horn-like projection on the head which is adapted for chemical defense, similar to the fontanellar gun of true nasute termites. However unlike true nasutes, the mandibles of the soldiers are functional and highly developed, and they are unable to expel their chemical weaponry at a distance – instead relying on direct physical contact. Some genera, such as Syntermes or Labiotermes, have a highly reduced nasus and in some species it may appear absent altogether. Although the Syntermitinae were once grouped and considered basal within the Nasutitermitinae, they are not closely related with modern cladistic analyses showing Syntermitinae to be a separate and distinct lineage that is more closely related to either the Amitermes-group or MicrocerotermesTermitinae. It is believed the nasus evolved independently in Syntermitinae in an example of convergent evolution. Genera range from southern Mexico (Cahuallitermes) to Northern Argentina with the highest diversity occurring in the Brazilian Cerrado.