Threitol

Last updated
Threitol [1]
Threitol.png
Names
Systematic IUPAC name
(2R,3R)-Butane-1,2,3,4-tetrol
Other names
(2R,3R)-Butane-1,2,3,4-tetraol (not recommended)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.150.149
KEGG
PubChem CID
UNII
Properties
C4H10O4
Molar mass 122.12
AppearanceSolid
Melting point 88 to 90 °C (190 to 194 °F; 361 to 363 K)
Hazards
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Threitol is a four-carbon sugar alcohol with the molecular formula C4H10O4. It is primarily used as an intermediate in the chemical synthesis of other compounds. It is the diastereomer of erythritol.

Contents

In living things, threitol is found in the edible fungus Armillaria mellea . [2] It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle Upis ceramboides . [3]

See also

Related Research Articles

Beetle Order of insects

Beetles are a group of insects that form the order Coleoptera, in the superorder Endopterygota. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 400,000 species, is the largest of all orders, constituting almost 40% of described insects and 25% of all known animal life-forms; new species are discovered frequently. The largest of all families, the Curculionidae (weevils), with some 83,000 member species, belongs to this order. Found in almost every habitat except the sea and the polar regions, they interact with their ecosystems in several ways: beetles often feed on plants and fungi, break down animal and plant debris, and eat other invertebrates. Some species are serious agricultural pests, such as the Colorado potato beetle, while others such as Coccinellidae eat aphids, scale insects, thrips, and other plant-sucking insects that damage crops.

Ethylene glycol chemical compound

Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, sweet-tasting, viscous liquid. Ethylene glycol is toxic. Household pets are especially susceptible to ethylene glycol poisoning from vehicle antifreeze leaks.

Cryobiology is the branch of biology that studies the effects of low temperatures on living things within Earth's cryosphere or in science. The word cryobiology is derived from the Greek words κρῧος [kryos], "cold", βίος [bios], "life", and λόγος [logos], "word". In practice, cryobiology is the study of biological material or systems at temperatures below normal. Materials or systems studied may include proteins, cells, tissues, organs, or whole organisms. Temperatures may range from moderately hypothermic conditions to cryogenic temperatures.

Antifreeze protein proteins that bind to ice and modify the growth of ice crystals

Antifreeze proteins (AFPs) or ice structuring proteins (ISPs) refer to a class of polypeptides produced by certain animals, plants, fungi and bacteria that permit their survival in subzero environments. AFPs bind to small ice crystals to inhibit the growth and recrystallization of ice that would otherwise be fatal. There is also increasing evidence that AFPs interact with mammalian cell membranes to protect them from cold damage. This work suggests the involvement of AFPs in cold acclimatization.

Antifreeze Coolant additive which reduces the freezing point of water

An antifreeze is an additive which lowers the freezing point of a water-based liquid. An antifreeze mixture is used to achieve freezing-point depression for cold environments. Common antifreezes increase the boiling point of the liquid, allowing higher coolant temperature.

The just-world hypothesis or just-world fallacy is the cognitive bias that a person's actions are inherently inclined to bring morally fair and fitting consequences to that person, to the end of all noble actions being eventually rewarded and all evil actions eventually punished. In other words, the just-world hypothesis is the tendency to attribute consequences to—or expect consequences as the result of—a universal force that restores moral balance. This belief generally implies the existence of cosmic justice, destiny, divine providence, desert, stability, and/or order, and is often associated with a variety of fundamental fallacies, especially in regard to rationalizing people's suffering on the grounds that they "deserve" it.

Cucujidae Family of beetles

The Cucujidae, "flat bark beetles," are a family of distinctively flat beetles found worldwide under the bark of dead trees. The family has received considerable taxonomic attention in recent years and now consists of 59 species distributed in four genera.

A cryoprotectant is a substance used to protect biological tissue from freezing damage. Arctic and Antarctic insects, fish and amphibians create cryoprotectants in their bodies to minimize freezing damage during cold winter periods. Cryoprotectants are also used to preserve living materials in the study of biology and to preserve food products.

Undergraduate Texts in Mathematics (UTM) is a series of undergraduate-level textbooks in mathematics published by Springer-Verlag. The books in this series, like the other Springer-Verlag mathematics series, are small yellow books of a standard size.

Insect winter ecology describes the overwinter survival strategies of insects, which are in many respects more similar to those of plants than to many other animals, such as mammals and birds. Unlike those animals, which can generate their own heat internally (endothermic), insects must rely on external sources to provide their heat (ectothermic). Thus, insects persisting in winter weather must tolerate freezing or rely on other mechanisms to avoid freezing. Loss of enzymatic function and eventual freezing due to low temperatures daily threatens the livelihood of these organisms during winter. Not surprisingly, insects have evolved a number of strategies to deal with the rigors of winter temperatures in places where they would otherwise not survive.

<i>Cucujus</i> Genus of beetles

Cucujus is a genus of beetles in the family Cucujidae, the flat bark beetles. It contains 19 currently recognized species and subspecies.

Ethylene glycol poisoning is poisoning caused by drinking ethylene glycol. Early symptoms include intoxication, vomiting and abdominal pain. Later symptoms may include a decreased level of consciousness, headache, and seizures. Long term outcomes may include kidney failure and brain damage. Toxicity and death may occur after drinking even a small amount.

Cryopreservation Process where biological matter is preserved by cooling to very low temperatures

Cryo-preservation or cryo-conservation is a process where organelles, cells, tissues, extracellular matrix, organs, or any other biological constructs susceptible to damage caused by unregulated chemical kinetics are preserved by cooling to very low temperatures. At low enough temperatures, any enzymatic or chemical activity which might cause damage to the biological material in question is effectively stopped. Cryopreservation methods seek to reach low temperatures without causing additional damage caused by the formation of ice crystals during freezing. Traditional cryopreservation has relied on coating the material to be frozen with a class of molecules termed cryoprotectants. New methods are constantly being investigated due to the inherent toxicity of many cryoprotectants. By default it should be considered that cryopreservation alters or compromises the structure and function of cells unless it is proven otherwise for a particular cell population. Cryoconservation of animal genetic resources is the process in which animal genetic material is collected and stored with the intention of conservation of the breed.

Xylomannan is an antifreeze molecule, found in the freeze-tolerant Alaskan beetle Upis ceramboides. Unlike antifreeze proteins, xylomannan is not a protein. Instead, it is a combination of a sugar (saccharide) and a fatty acid that is found in cell membranes. As such is expected to work in a different manner than AFPs. It is believed to work by incorporating itself directly into the cell membrane and preventing the freezing of water molecules within the cell.

<i>Upis ceramboides</i> species of beetle

Upis ceramboides is a species of beetle, one of many wood-living insects that benefit from forest fires. It often occurs in quantities below the bark on the fire-damaged birches, but can sometimes be seen on other deciduous trees such as willow and aspen. The larvae thrive in the inner bark which is rich in mycelia, and in the sapwood. They develop into pupae during the summer months under the bark, and they develop over two or three years. The following spring they reproduce themselves.

RiAFP refers to an antifreeze protein (AFP) produced by the Rhagium inquisitor longhorned beetle. It is a type V antifreeze protein with a molecular weight of 12.8 kDa; this type of AFP is noted for its hyperactivity. R. inquisitor is a freeze-avoidant species, meaning that, due to its AFP, R. inquisitor prevents its body fluids from freezing altogether. This contrasts with freeze-tolerant species, whose AFPs simply depress levels of ice crystal formation in low temperatures. Whereas most insect antifreeze proteins contain cysteines at least every sixth residue, as well as varying numbers of 12- or 13-mer repeats of 8.3-12.5kDa, RiAFP is notable for containing only one disulfide bridge. This property of RiAFP makes it particularly attractive for recombinant expression and biotechnological applications.

Ethynerone chemical compound

Ethynerone, also known as 17α-(2-chloroethynyl)estra-4,9-dien-17β-ol-3-one, is a steroidal progestin of the 19-nortestosterone group that was first reported in 1961 but was never marketed. Under the developmental code name MK-665, it was studied in combination with mestranol as an oral contraceptive. Development of the drug was discontinued due to concerns surrounding toxicity findings in dogs. It is a chloroethynylated derivative of norethisterone.

Flumexadol

Flumexadol (INN) is a drug described and researched as a non-opioid analgesic which was never marketed. It has been found to act as an agonist of the serotonin 5-HT1A and 5-HT2C receptors and, to a much lesser extent, of the 5-HT2A receptor. According to Nilsson (2006) in a paper on 5-HT2C receptor agonists as potential anorectics, "The (+)-enantiomer of this compound showed [...] affinity for the 5-HT2C receptor (Ki) 25 nM) [...] and was 40-fold selective over the 5-HT2A receptor in receptor binding studies. Curiously, the racemic version [...], also known as 1841 CERM, was originally reported to possess analgesic properties while no association with 5-HT2C receptor activity was mentioned." It is implied that flumexadol might be employable as an anorectic in addition to analgesic. Though flumexadol itself has never been approved for medical use, oxaflozane is a prodrug of the compound that was formerly used clinically in France as an antidepressant and anxiolytic agent.

Epiestriol chemical compound

Epiestriol (INN), or epioestriol (BAN), also known as 16β-epiestriol or simply 16-epiestriol as well as 16β-hydroxy-17β-estradiol, is a minor and weak endogenous estrogen, and the 16β-epimer of estriol. Epiestriol is used clinically in the treatment of acne. In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids like hydrocortisone.

<i>Cucujus clavipes</i> Species of beetle

Cucujus clavipes is known as the flat bark beetle. It is found throughout North America. These are generally found near tree line under bark of dead poplar and ash trees. C. clavipes are described as phloem-feeding and often predators of other small insects, such as wood-boring beetles, and mites. These are usually seen during spring-summer seasons. Having a cold habitat, these beetles must go through several physiological mechanisms to survive; they are recognised for their ability to change their overwintering mechanisms.

References

  1. Threitol at Sigma-Alrich
  2. Elks, J.; Ganellin, C. R. (1990). "Dictionary of Drugs". doi:10.1007/978-1-4757-2085-3. ISBN   978-1-4757-2087-7.Cite journal requires |journal= (help)
  3. Walters, K. R. Jr; Pan, Q.; Serianni, A. S.; Duman, J. G. (2009). "Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides". Journal of Biological Chemistry . 284 (25): 16822–16831. doi:10.1074/jbc.M109.013870. PMC   2719318 . PMID   19403530.