Epoxides

chemical compound

Scopolamine, also known as hyoscine, or '''Devil's Breath''', is a medication used to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.

thumb|A generic epoxide

Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis. It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms. Out of concerns of developing resistance, use for greater than ten days is not recommended. It is used as a cream or ointment applied to the skin.

Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels–Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Fosfomycin, sold under the brand name Monurol among others, is an antibiotic primarily used to treat lower urinary tract infections. It is not indicated for kidney infections. Occasionally it is used for prostate infections. It is generally taken by mouth.

Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510–525 nm and absorbing significantly in the range of 450 to 540 nm.

chemical compound

pharmaceutical drug

Endrin is an organochlorine compound with the chemical formula C12H8Cl6O that was first produced in 1950 by Shell and Velsicol Chemical Corporation. It was primarily used as an insecticide, as well as a rodenticide and piscicide. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex. The compound became infamous as a persistent organic pollutant, and for this reason it is banned in many countries.

chemical compound

Violaxanthin is a xanthophyll pigment with an orange color found in a variety of plants. Violaxanthin is the product of the epoxidation of zeaxanthin where the oxygen atoms are from reactive oxygen species (ROS). Such ROS's arise when a plant is subject to solar radiation so intense that the light cannot all be absorbed by the chlorophyll.

Eplerenone, sold under brand name Inspra among others, is an aldosterone antagonist used primarily in the treatment of heart failure with reduced ejection fraction (HFrEF), particularly following myocardial infarction. It may also be considered as an add-on therapy in resistant hypertension; however, the majority of evidence in this setting supports the use of spironolactone (another drug in a same class), with fewer studies directly evaluating eplerenone.

Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum (Gibberella zeae) and F. culmorum, both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or fusarium ear blight in corn. The incidence of fusarium head blight is strongly associated with moisture at the time of flowering (anthesis),

Glycidol is an organic compound with the formula . The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is an insecticide used particularly in organic farming.

chemical reaction

chemical compound

chemical reaction of a ketone or aldehyde with an α-haloester in the presence of a base to form an α,β-epoxy ester

'(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene') is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François Guillaume Boullay (1777–1869) in 1812. The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison). A mixture of two different compounds, picrotoxin occurs naturally in the fruit of the Anamirta cocculus plant, although it can also be synthesized chemically.

Peridinin is a light-harvesting apocarotenoid, a pigment associated with chlorophyll and found in the peridinin-chlorophyll-protein (PCP) light-harvesting complex in dinoflagellates, best studied in Amphidinium carterae.

Carfilzomib, sold under the brand name Kyprolis, is an anti-cancer medication acting as a selective proteasome inhibitor. Chemically, it is a tetrapeptide epoxyketone and an analog of epoxomicin. It was developed by Onyx Pharmaceuticals.

Troleandomycin (TAO for short) is a macrolide antibiotic. It was sold in Italy (branded Triocetin) and Turkey (branded Tekmisin). It is no longer sold in Italy as of 2018.

chemical compound

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.

thumbnail|left|all-trans Neoxanthin Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is often present in two forms: all-trans and 9-cis isomers. It is produced from violaxanthin, but a suspected neoxanthin synthase is still to be confirmed. Two different genes were confirmed to be implied in violaxanthin conversion to neoxanthin in Arabidopsis and tomato. It has a specific role in protection against photooxidative stress. It is a major xanthophyll found in green leafy vegetables such as spinach.

Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is a pharmaceutical drug developed by Bristol-Myers Squibb as a chemotherapeutic medication for cancer.

chemical compound

Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism Aspergillus fumigatus.

Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare). It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.

Oleandomycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces antibioticus. It is weaker than erythromycin.

pharmaceutical drug

Antheraxanthin (from ánthos, Greek for "flower" and xanthos, Greek for "yellow") is a bright yellow accessory pigment found in many organisms that perform photosynthesis. It is a xanthophyll cycle pigment, an oil-soluble alcohol within the xanthophyll subgroup of carotenoids. Antheraxanthin is both a component in and product of the cellular photoprotection mechanisms in photosynthetic green algae, red algae, euglenoids, and plants.

chemical compound

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;" ! | Epothilones |- | align="center" colspan="2" bgcolor="#ffffff"| 250px|Epothilones A (R = H) and B (R = Me) Epothilones A (R = H) and B (R = CH3) |- | Chemical formulae | A: C26H39NO6S B: C27H41NO6S |- | Molecular masses | A: 493.66 g/mol B: 507.68 g/mol |- | CAS numbers | A: 152044-53-6 B: 152044-54-7 |- | PubChem | A: 448799 B: 448013 |- | align="center" colspan="2" bgcolor="#ffffff"| 250px|Epothilones C (R = H) and D (R = Me) Epothilones C (R = H) and D (R = CH3) |- | Chemi

thumb|Withaferin A thumb|Salpichrolid A thumb|Nicandrenon-1 thumb|Ixocarpalacton A Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton. They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo.

Maitansine (INN), or maytansine (USAN), is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site. The maytansine binding site and binding mode has been characterized.

Trichodermin is a trichothecene. It inhibits protein formation in Euchariotes.

chemical compound

Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia (fungal cells). Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals (mainly wheat, barley, rye and triticale), soybeans, banana, rice, coffee

Satratoxin-H, a trichothecene mycotoxin, is a naturally occurring toxin produced by the ascomycetes Stachybotrys chartarum and Trichoderma cornu-damae which is highly toxic and potentially fatal to humans and other animals. The clinical condition it causes is known as Stachybotrotoxicosis. It is related to the mycotoxin T-2, but unlike T-2 has not been reported to have been used as a chemical weapon.

Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus.

Xanthoxin is an intermediate in the biosynthesis of the plant hormone abscisic acid.

thumb|Diatoms, such as the diatom pictured here [[Phaeodactylum tricornutum, often contain diadinoxanthin pigments.]] Diadinoxanthin is a pigment found in phytoplankton. It has the formula C40H54O3. It gives rise to the xanthophylls diatoxanthin and dinoxanthin.

chemical compound

Etoglucid is a drug used in chemotherapy. It is an epoxide compound.

thumb|right|Chemical structure of the prototypical limonoid limonin

chemical compound

cycloaliphatic epoxide

Nivalenol (NIV) is a mycotoxin of the trichothecene group. In nature it is mainly found in fungi of the Fusarium species. The Fusarium species belongs to the most prevalent mycotoxin producing fungi in the temperate regions of the northern hemisphere, therefore making them a considerable risk for the food crop production industry.

chemical compound

Elephantopin is a natural chemical compound extracted from the Elephantopus elatus plant of the genus Elephantopus, family Compositae. It is a sesquiterpene lactone with a germacranolide skeleton, containing two lactone rings and an epoxide functional group.

Mezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species. All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is

Galanolactone is a diterpenoid lactone first isolated from ginger. It is present in acetone extracts of ginger, and appears to be an antagonist at 5-HT3 receptors.

chemical compound

Triptolide is a diterpenoid epoxide which is produced by the thunder god vine, Tripterygium wilfordii. It has in vitro and in vivo activities against mouse models of polycystic kidney disease and pancreatic cancer, but its physical properties and severe toxicity limit its therapeutic potential. Consequently, a synthetic water-soluble prodrug, minnelide, is being studied clinically instead.

chemical compound