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Preferred IUPAC name 3-[2,5-Dioxo-3-(propan-2-yl)-2,5-dihydro-1H-pyrrol-1-yl]propanoic acid | |
Other names 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid | |
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Properties | |
C10H13NO4 | |
Molar mass | 211.217 g·mol−1 |
Appearance | White powder |
Melting point | 75 to 77 °C (167 to 171 °F; 348 to 350 K) |
Solubility | CH2Cl2, acetone, toluene, CH3OH |
Vapor pressure | 0 mmHg (25 °C) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Farinomalein is a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan). [1]
Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae . [2] These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean. [2]
A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported. [3] Firstly, the furanone is oxidized to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane, followed by acetic acid reflux with beta-alanine. The white powdered product has a melting point of 75-77 °C.
Ophiocordyceps sinensis is known in English colloquially as caterpillar fungus, or by its more prominent names dōng chóng xià cǎo, literally "winter worm, summer grass"), or yartsa gunbu (Tibetan: དབྱར་རྩྭ་དགུན་འབུ་, Wylie: dbyar rtswa dgun 'bu, or Yarsa-gumba or Yarcha-gumba, or Keeda Jadi, or ရှီးပတီး. It is an entomopathogenic fungus in the family Ophiocordycipitaceae. It is mainly found in the meadows above 3,500 metres on the Tibetan Plateau in Southwest China and the Himalayan regions of Bhutan and Nepal. It parasitizes larvae of ghost moths and produces a fruiting body which used to be valued as a herbal remedy and in traditional Chinese medicine. Caterpillar fungus contains the compound cordycepin, an adenosine derivative. However, the fruiting bodies harvested in nature usually contain high amounts of arsenic and other heavy metals so they are potentially toxic and sales have been strictly regulated by the CFDA since 2016.
Beauveria bassiana is a fungus that grows naturally in soils throughout the world and acts as a parasite on various arthropod species, causing white muscardine disease; it thus belongs to the entomopathogenic fungi. It is used as a biological insecticide to control a number of pests, including termites, thrips, whiteflies, aphids and various beetles. Its use in the control of bedbugs and malaria-transmitting mosquitos is under investigation.
Maleimide is a chemical compound with the formula H2C2(CO)2NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Maleimides also describes a class of derivatives of the parent maleimide where the NH group is replaced with alkyl or aryl groups such as a methyl or phenyl, respectively. The substituent can also be a small molecule (such as biotin, a fluorescent dye, an oligosaccharide, or a nucleic acid), a reactive group, or a synthetic polymer such as polyethylene glycol. Human hemoglobin chemically modified with maleimide-polyethylene glycol is a blood substitute called MP4.
An entomopathogenic fungus is a fungus that can act as a parasite of insects and kills or seriously disables them.
Phytophthora sojae is an oomycete and a soil-borne plant pathogen that causes stem and root rot of soybean. This is a prevalent disease in most soybean growing regions, and a major cause of crop loss. In wet conditions the pathogen produces zoospores that move in water and are attracted to soybean roots. Zoospores can attach to roots, germinate, and infect the plant tissues. Diseased roots develop lesions that may spread up the stem and eventually kill the entire plant. Phytophthora sojae also produces oospores that can remain dormant in the soil over the winter, or longer, and germinate when conditions are favourable. Oospores may also be spread by animals or machinery.
Furaneol, or strawberry furanone, is an organic compound used in the flavor and perfume industry. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents.
Streptogramin B is a subgroup of the streptogramin antibiotics family. These natural products are cyclic hexa- or hepta depsipeptides produced by various members of the genus of bacteria Streptomyces. Many of the members of the streptogramins reported in the literature have the same structure and different names; for example, pristinamycin IA = vernamycin Bα = mikamycin B = osteogrycin B.
Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.
Acetosyringone is a phenolic natural product and a chemical compound related to acetophenone and 2,6-dimethoxyphenol. It was first described in relation to lignan/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.
Hexacyclinol is a natural metabolite of a fungus, Panus rudis. Significant controversy surrounded its proposed structure until its total synthesis by John Porco, Jr. in 2006.
Isaria sinclairii is a species of entomopathogenic fungus mostly infecting the underground nymphs of cicadas. It produces myriocin, from which the synthetic drug fingolimod, a treatment for multiple sclerosis, was developed.
Purpureocillium is a fungal genus in the Ophiocordycipitaceae family. The genus now contains at least 5 species with the type species Purpureocillium lilacinum, a common saprobic, filamentous fungus. It has been isolated from a wide range of habitats, including cultivated and uncultivated soils, forests, grassland, deserts, estuarine sediments and sewage sludge, and insects. It has also been found in nematode eggs, and occasionally from females of root-knot and cyst nematodes. In addition, it has frequently been detected in the rhizosphere of many crops. The species can grow at a wide range of temperatures – from 8 to 38 °C for a few isolates, with optimal growth in the range 26 to 30 °C. It also has a wide pH tolerance and can grow on a variety of substrates. P. lilacinum has shown promising results for use as a biocontrol agent to control the growth of destructive root-knot nematodes.
Purpureocillium lilacinum is a species of filamentous fungus in the family Ophiocordycipitaceae. It has been isolated from a wide range of habitats, including cultivated and uncultivated soils, forests, grassland, deserts, estuarine sediments and sewage sludge, and insects. It has also been found in nematode eggs, and occasionally from females of root-knot and cyst nematodes. In addition, it has frequently been detected in the rhizosphere of many crops. The species can grow at a wide range of temperatures – from 8 to 38 °C for a few isolates, with optimal growth in the range 26 to 30 °C. It also has a wide pH tolerance and can grow on a variety of substrates. P. lilacinum has shown promising results for use as a biocontrol agent to control the growth of destructive root-knot nematodes.
Coffee furanone (2-methyltetrahydrofuran-3-one) is a pleasant smelling liquid furan derivative which is a volatile constituent of the aroma complex of roasted coffee. Coffee furanone is less odorous than furfuryl mercaptan, which with an odor threshold of 0.005 ppb was the first high impact aroma chemical, but has a very pleasant sweet caramel character, with some nuttiness.
Paecilomyces variotii is a common environmental mold that is widespread in composts, soils and food products. It is known from substrates including food, indoor air, wood, soil and carpet dust. Paecilomyces variotii is the asexual state of Byssochlamys spectabilis, a member of the Phylum Ascomycota. However, the Byssochlamys state is rarely observed in culture due to the heterothallic nature of this species. Paecilomyces variotii is fast growing, producing powdery to suede-like colonies that are yellow-brown or sand-colored. It is distinguishable from microscopically similar microfungi, such as the biverticillate members of the genus Penicillium by its broadly ellipsoidal to lemon-shaped conidia, loosely branched conidiophores and phialides with pointed tips. Ascospores of the sexual state, B. spectabilis, are strongly heat-resistant. As such, the fungus is a common contaminant of heat-treated foods and juices. It is also known from decaying wood and creosote-treated wood utility poles. Paecilomyces variotii has been associated with a number of infective diseases of humans and animals. It is also an important indoor environmental contaminant.
Streptomyces virginiae is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces virginiae produces actithiazic acid, virginiamycins and cycloserine. Streptomyces virginiae also produces monensin A, monensin B, monensin C, monensin D, actithiazic acid.
Tetronic acid is a chemical compound, classified as a γ-lactone, with the molecular formula C4H4O3.
Isaria fumosorosea is an entomopathogenic fungus, formerly known as Paecilomyces fumosoroseus. It shows promise as a biological pesticide with an extensive host range.
Paecilomyces marquandii is a soil-borne filamentous fungus distributed throughout temperate to tropical latitudes worldwide including forest, grassland, sewage sludge and strongly metal polluted area characterized by high tolerance in heavy metals. Simultaneous toxic action of zinc and alachlor result an increase in uptake of metal in this fungus but disrupts the cell membrane. Paecilomyces marquandii is known to parasitize the mushroom, Cuphophyllus virgineus, in the family, Hygrophoraceae. Paecilomyces marquandii is categorised as a biosafety risk group 1 in Canada and is not thought to be a significant pathogen of humans or animals.
Podospora appendiculata is a coprophilous fungus that is most commonly found in the dung of lagomorphs, such as hares and rabbits, in temperate to warm climates. A member of the division Ascomycota, P. appendiculata is characterized by ovoid, hair-studded perithecia which can bear a distinctive violaceous colouring and peridia which are coriaceous, or leathery, in texture. Podospora appendiculata has been shown to produce three compounds with antimicrobial properties.