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| Names | |
|---|---|
| IUPAC name oxacyclohenicosan-2-one | |
| Other names 20-Eicosanolide | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
PubChem CID | |
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| Properties | |
| C20H38O2 | |
| Molar mass | 310.522 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Eicosanolide is an organic compound with the chemical formula C20H38O2. It is a cyclic ester or lactone, more specifically a macrolide.
Eicosanolide is used by several species of bees (such as some of genera Colletes, Lasioglossum, Halictus ) and butterflies (such as some of genus Heliconius ) as a pheromone. [1] The Dufour's gland of bees in the Halictinae subfamily, contains eicosanolide along with other macrocyclic lactones, which could be used for a range of different applications like nest building, larval food and chemical communication. [2] [3] [4]
Bees are winged insects closely related to wasps and ants, known for their roles in pollination and, in the case of the best-known bee species, the western honey bee, for producing honey. Bees are a monophyletic lineage within the superfamily Apoidea. They are currently considered a clade, called Anthophila. There are over 20,000 known species of bees in seven recognized biological families. Some species – including honey bees, bumblebees, and stingless bees – live socially in colonies while most species (>90%) – including mason bees, carpenter bees, leafcutter bees, and sweat bees – are solitary.
Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but has since been used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.
Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Some contain heteroatoms replacing one or more carbon atoms of the ring.
Halictidae is the second-largest family of bees with nearly 4,500 species. They are commonly called sweat bees, as they are often attracted to perspiration. Halictid species are an extremely diverse group that can vary greatly in appearance. These bees occur all over the world and are found on every continent except Antarctica. Usually dark-colored and often metallic, halictids are found in various sizes, colors and patterns. Several species are all or partly green and a few are red, purple, or blue. A number of them have yellow markings, especially the males, which commonly have yellow faces, a pattern widespread among the various families of bees. The family is one of many with short tongues and is best distinguished by the arcuate basal vein found on the wing. Females in this family tend to be larger than the males. They are the group for which the term 'eusocial' was first coined by entomologist, Suzanne Batra.
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.
With over 850 species, the genus Nomada is one of the largest genera in the family Apidae, and the largest genus of cuckoo bees. Cuckoo bees are so named because they enter the nests of a host and lay eggs there, stealing resources that the host has already collected. The name "Nomada" is derived from the Greek word nomas, meaning "roaming" or "wandering."
Lasioglossum malachurum, the sharp-collared furrow bee, is a small European halictid bee. This species is obligately eusocial, with queens and workers, though the differences between the castes are not nearly as extreme as in honey bees. Early taxonomists mistakenly assigned the worker females to a different species from the queens. They are small, shiny, mostly black bees with off-white hair bands at the bases of the abdominal segments. L. malachurum is one of the more extensively studied species in the genus Lasioglossum, also known as sweat bees. Researchers have discovered that the eusocial behavior in colonies of L. malachurum varies significantly dependent upon the region of Europe in which each colony is located.
Bombus lapidarius is a species of bumblebee in the subgenus Melanobombus. Commonly known as the red-tailed bumblebee, B. lapidarius can be found throughout much of Central Europe. Known for its distinctive black and red body, this social bee is important in pollination.
Bombus lucorum, the white-tailed bumblebee, is a species of bumblebee, widespread and common throughout Europe. This name has been widely used for a range of nearly identical-looking or cryptic species of bumblebees. In 1983, Scholl and Obrecht even coined the term Bombus lucorum complex to explain the three taxa that cannot be easily differentiated from one another by their appearances. A recent review of all of these species worldwide has helped to clarify its distribution in Europe and northern Asia, almost to the Pacific. B. lucorum reaches the Barents Sea in the North. However, in southern Europe, although found in Greece it is an upland species with its distribution never quite reaching the Mediterranean.
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.
Eucera is a genus of bees in the family Apidae, which comprises more than 100 species. These bees are commonly known as long-horned bees due to their characteristically long antennae, especially in males. Eucera species can be found in diverse habitats, including meadows, fields, and urban gardens, primarily in the Palearctic and Nearctic regions, covering parts of Europe, Asia, North Africa, and North America.
Dufour's gland is an abdominal gland of certain insects, part of the anatomy of the ovipositor or sting apparatus in female members of Apocrita. The diversification of Hymenoptera took place in the Cretaceous and the gland may have developed at about this time as it is present in all three groups of Apocrita, the wasps, bees and ants.
Parischnogaster jacobsoni is a species of social wasp within Parischnogaster, the largest and least known genus of Stenogastrinae. It is distinguished mainly by its tendency to construct ant guards on its nests. Natural selection has led this wasp to have a thick substance emitted from its abdominal glands that allows it to protect its nest from invasions. Parischnogaster as a genus has been relatively unstudied; P. jacobsoni is one of the few investigated species because it has sufficient durability to live near human populations and it has demonstrated unusual resilience to pollution. While P. jacobsoni is a more complex organism than other wasps in Parischnogaster, the genus overall is relatively primitive with respect to social wasps as a whole.
Xylocopa micans, also known as the southern carpenter bee, is a species of bee within Xylocopa, the genus of carpenter bees. The southern carpenter bee can be found mainly in the coastal and gulf regions of the southeastern United States, as well as Mexico and Guatemala. Like all Xylocopa bees, X. micans bees excavate nests in woody plant material. However, unlike its sympatric species Xylocopa virginica, X. micans has not been found to construct nest galleries in structural timbers of building, making it less of an economic nuisance to humans. Carpenter bees have a wide range of mating strategies between different species. The southern carpenter bee exhibits a polymorphic mating strategy, with its preferred method of mating changing as the season progresses from early spring to mid summer. Like most bees in its genus, the southern carpenter bee is considered a solitary bee because it does not live in colonies.
Messor capitatus is an ant species part of the genus Messor. This genus includes about 40 specialized species that are found in dry areas of Mediterranean countries such as Africa, Southern Europe, and Asia. Messor capitatus are known as an Old World species because they release trail pheromones from the Dufour gland instead of from poison glands. Messor capitatus are known as individual foragers that collect food independently of one another but sometimes will also use group foraging to form irregular, broad columns. Messor capitatus main food source is seeds but they also will eat remains of plants and animals.
Hylaeus modestus, also known as the modest masked bee, is a species of hymenopteran in the family Colletidae. It is found in North America.
Corey–Nicolaou macrolactonization is a named reaction of organic chemistry, for the synthesis of lactones from hydroxy acids, found in 1974. The reaction uses 2,2'-dipyridyldisulfide and triphenylphosphine as reagents and runs in polar aprotic solvent under mild conditions.
Toxungen comprises a secretion or other body fluid of one or more biological toxins that is transferred by one animal to the external surface of another animal via a physical delivery mechanism. Toxungens can be delivered through spitting, spraying, or smearing. As one of three categories of biological toxins, toxungens can be distinguished from poisons, which are passively transferred via ingestion, inhalation, or absorption across the skin, and venoms, which are delivered through a wound generated by a bite, sting, or other such action. Toxungen use offers the evolutionary advantage of delivering toxins into the target's tissues without the need for physical contact.
Octadecanolide is an organic compound with the chemical formula C18H34O2. It is a cyclic ester or lactone, more specifically a macrolide.
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