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Lotaustralin
Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil (''Lotus australis''), cassava (''Manihot esculenta''), lima bean (''Phaseolus lunatus''), roseroot (''Rhodiola rosea'') and white clover (''Trifolium repens''), among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is .... References {{Glycosides Cyanogenic glycosides Glucosides Plant toxins ...
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Lotus Australis
''Lotus australis'', known by its common name of austral trefoil, is a small, spreading herb from the family Fabaceae. It normally grows to around 30–50 cm in height and is native to Australia. Leaves are of a trifoliate shape and are small, with a light green colour. During spring, the plant bursts into beautiful massed displays of white pea flowers. In summer, these are replaced with stiff, tubular beans, which explode when they dry, releasing multiple small, black legume seeds. Austral trefoil is easily propagated from these seeds, by soaking the seeds in hot water overnight before sowing. This mimics the heat of a bushfire, which is a contributing factor in germination in the wild. ''Lotus australis'' is one of just a few plants in which the cyanogenic glucoside known as lotaustralin Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil (''Lotus australis''), cassava (''Manihot esculenta''), lima bean (''Phaseolus lunatus''), ro ...
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Ethyl Acetate
Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. Production and synthesis Ethyl acetate was first synthesized by the Louis-Léon de Brancas, Count de Lauraguais in 1759 by distilling a mixture of ethanol and acetic acid. In 2004, an estimated 1.3 million tonnes were produced worldwide. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in 2018. Ethyl acetate is produced in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% ...
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Cyanohydrin
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is , where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst: : In this reaction, the nucleophilic ion attacks the electrophilic carbonyl carbon in the ketone, followed by protonation by HCN, thereby regenerating the cyanide anion. Cyanohydrins are also prepared by displacement of sulfite by cyanide salts: : Cyanohydrins are intermediates in the Strecker amino acid synthesis. In aqueous acid, they are hydrolyzed to the α-hydroxy acid. Preparative methods Cyanohydrins are traditionally prepared b ...
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Cyanogenic Glycosides
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of ''Heliconius'' butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a ''C-glycoside'') glycosidic bond. According to the ...
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Hydrogen Cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is produced on an industrial scale and is a highly valued Precursor (chemistry), precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its Volatility (chemistry), volatile nature. A solution of hydrogen cyanide in water (molecule), water, represented as HCN(aqueous, aq), is called ''hydrocyanic acid''. The Salt (chemistry), salts of the cyanide anion are known as cyanides. Whether hydrogen cyanide is an organic compound or not is a topic of debate among chemists, and opinions vary from author to author. Traditionally, it is considered ino ...
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Glucose
Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. It is used by plants to make cellulose, the most abundant carbohydrate in the world, for use in cell walls, and by all living Organism, organisms to make adenosine triphosphate (ATP), which is used by the cell as energy. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as amylose and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form is -glucose, while its Stereoisomerism, stereoisomer L-glucose, -glucose is produced synthetically in comparatively small amounts and is less biologicall ...
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Linamarase
Linamarase, or beta-D-glucosidase (), is an enzyme found in many plants including cassava and the butter bean. In cassava it is found in the cell walls. When the plant is chewed or ground, it exposes the enzyme to compounds like linamarin and lotaustralin which release cyanide compounds that can be lethal to the eater. In humans, chronic toxicity is more likely than death. This action of the enzyme is used by many cultures to process cassava into an edible substance. The enzyme converts the cyanide containing compounds into acetone cyanohydrin, which spontaneously decomposes to hydrogen cyanide (HCN). The HCN then either dissolves readily in water or is released into the air. Not all cyanide can be removed during processing. Linamarase can be inhibited by low pH via a dilute acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a co ...
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Enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different molecules known as product (chemistry), products. Almost all metabolism, metabolic processes in the cell (biology), cell need enzyme catalysis in order to occur at rates fast enough to sustain life. Metabolic pathways depend upon enzymes to catalyze individual steps. The study of enzymes is called ''enzymology'' and the field of pseudoenzyme, pseudoenzyme analysis recognizes that during evolution, some enzymes have lost the ability to carry out biological catalysis, which is often reflected in their amino acid sequences and unusual 'pseudocatalytic' properties. Enzymes are known to catalyze more than 5,000 biochemical reaction types. Other biocatalysts include Ribozyme, catalytic RNA molecules, also called ribozymes. They are sometimes descr ...
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Linamarin
Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. It is a glucoside of acetone cyanohydrin. Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide; hence food uses of plants that contain significant quantities of linamarin require extensive preparation and detoxification. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. Consumption of cassava products with low levels of linamarin is widespread in the low-land tropics. Ingestion of food prepared from insufficiently processed cassava roots with high linamarin levels has been associated with dietary toxicity, particularly with the upper motor neuron disease known as konzo to the African populations in which it was first described by Trolli and later through the research network initia ...
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Methyl Ethyl Ketone
Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts.Wilhelm Neier, Guenter Strehlke "2-Butanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran. Production Butanone may be produced by oxidation of 2-butanol. The dehydrogenation of 2-butanol is catalysed by copper, zinc, or bronze: :CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2 This is used to produce approximately 700 million kilograms yearly. Other syntheses that have been examined but not implemented include Wacker oxidation of 2-butene and oxidation of isobutylbenzene, which is analogous to the industrial production of ac ...
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Cyanide
In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This anion is extremely poisonous. Soluble cyanide salts such as sodium cyanide (NaCN), potassium cyanide (KCN) and tetraethylammonium cyanide () are highly toxic. Covalent cyanides contain the group, and are usually called nitriles if the group is linked by a single covalent bond to carbon atom. For example, in acetonitrile , the cyanide group is bonded to methyl . In tetracyanomethane , four cyano groups are bonded to carbon. Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus toxic. The cyano group may be covalently bonded to atoms different than carbon, e.g., in cyanogen azide , phosphorus tricyanide and trimethylsilyl cyanide . Hydrogen cyanide, or , is a highly volatile toxic liquid tha ...
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White Clover
''Trifolium repens'', the white clover, is a herbaceous perennial plant in the bean family Fabaceae (otherwise known as Leguminosae). It is native to Europe, including the British Isles, and central Asia and is one of the most widely cultivated types of clover. It has been widely introduced worldwide as a forage crop, and is now also common in most grassy areas (lawns and gardens) of North America, Australia and New Zealand. The species includes varieties often classed as small, intermediate and large, according to height, which reflects petiole length. The term 'white clover' is applied to the species in general, 'Dutch clover' is often applied to intermediate varieties (but sometimes to smaller varieties), and 'ladino clover' is applied to large varieties. Name The genus name, ''Trifolium'', derives from the Latin ', "three", and ', "leaf", so called from the characteristic form of the leaf, which almost always has three leaflets ( trifoliolate); hence the popular name ...
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