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Benzyl Isothiocyanate
Benzyl isothiocyanate (BITC) is an isothiocyanate found in plants of the mustard family. Occurrence It can be found in ''Alliaria petiolata'', pilu oil, and papaya seeds where it is the main product of the glucotropaeolin breakdown by the enzyme myrosinase. Activity Benzyl isothiocyanate, and other isothiocyanates in general, were found to be protective against pancreatic carcinogenesis ''in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...'' via expression of the '' p21/WAF1'' gene. A recent published study showed its restraining impact on obesity, fatty liver, and insulin resistance in diet-induced obesity mouse model. References Isothiocyanates Benzyl esters {{organic-compound-stub ...
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Sigma-Aldrich
Sigma-Aldrich (formally MilliporeSigma) is an American chemical, life science, and biotechnology company that is owned by the German chemical conglomerate Merck Group. Sigma-Aldrich was created in 1975 by the merger of Sigma Chemical Company and Aldrich Chemical Company. It grew through various acquisitions until it had over 9,600 employees and was listed on the Fortune 1000. The company is headquartered in St. Louis and has operations in approximately 40 countries. In 2015, the German chemical conglomerate Merck Group acquired Sigma-Aldrich for $17 billion. The company is currently a part of Merck's life science business and in combination with Merck's earlier acquired Millipore Corporation, Millipore, operates as MilliporeSigma. History Sigma Chemical Company of St. Louis and Aldrich Chemical Company of Milwaukee were both American specialty chemical companies when they merged in August 1975. The company grew throughout the 1980s and 1990s, with significant expansion in fac ...
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Isothiocyanate
In organic chemistry, isothiocyanate is the functional group , formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also known as mustard oils. An artificial isothiocyanate, phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation. Cruciferous vegetables, such as bok choy, broccoli, cabbage, cauliflower, kale, and others, are rich sources of glucosinolate precursors of isothiocyanates. Although there has been some basic research on how isothiocyanates might exert biological effects ''in vivo'', there is no high-quality evidence to date for its efficacy against human diseases. Structure Typical bond angles for and linkages in aryl isothiocyanates are 165° and 177°, respectively. The and distances are 117 and 158 pms. Synthesis and reactions Isothiocy ...
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Mustard Family
Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The leaves are simple (although are sometimes deeply incised), lack stipules, and appear alternately on stems or in rosettes. The inflorescences are terminal and lack bracts. The flowers have four free sepals, four free alternating petals, two shorter free stamens and four longer free stamens. The fruit has seeds in rows, divided by a thin wall (or septum). The family contains 372 genera and 4,060 accepted species. The largest genera are ''Draba'' (440 species), ''Erysimum'' (261 species), ''Lepidium'' (234 species), ''Cardamine'' (233 species), and ''Alyssum'' (207 species). The family contains the cruciferous vegetables, including species such as ''Brassica oleracea'' (cultivated as cabbage, kale, cauliflower, broccoli and collards), ...
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Alliaria Petiolata
''Alliaria petiolata'', or garlic mustard, is a biennial flowering plant in the mustard family (Brassicaceae). It is native to Europe, western and central Asia, north-western Africa, Morocco, Iberia and the British Isles, north to northern Scandinavia, and east to northern Pakistan and Xinjiang in western China. In the first year of growth, plants form clumps of round, slightly wrinkled leaves, that when crushed smell like garlic. The plants flower in spring of the next year, producing cross shaped white flowers in dense clusters. As the flowering stems bloom they elongate into a spike-like shape. When flowering is complete, plants produce upright fruits that release seeds in mid-summer. Plants are often found growing along the margins of hedges, giving rise to the old British folk name of jack-by-the-hedge. Other common names include: garlic mustard, garlic root, hedge garlic, sauce-alone, jack-in-the-bush, penny hedge and poor man's mustard. The genus name ''Alliaria'', "res ...
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Pilu Oil
Pilu oil is an extract from seeds of the Pilu tree (''Salvadora persica''), also known as the toothbrush tree. It is used for soaps, detergents, and resist dyeing. Characteristics The oil comes from the seed and kernel. The percentage of the oil in seeds is 32-34%. The seed contains a brittle shell on the outer surface, and the kernel accounts for 60% in dried seed, containing 40-43% oil. ‘Sweet Variety’ of Pilu yields 35-44% oil which has a strong odour. The odour is due to the presence of Benzyl isothiocyanate in the oil. There is greenish yellow fat called Khakan fat. The purified fat is free from foul odour and has an agreeable taste. It is snow white. The oil is rich in lauric and myristic acids. It has a high melting point and a disagreeable odour that disappears on purification. The most important aspect of the oil is the presence of a low percentage of C8 and C10 fatty acids that are of great economic significance. The oil is an alternative source of oil for soa ...
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Papaya
The papaya (, ), papaw, () or pawpaw () is the plant species ''Carica papaya'', one of the 21 accepted species in the genus ''Carica'' of the family Caricaceae. It was first domesticated in Mesoamerica, within modern-day southern Mexico and Central America. In 2020, India produced 43% of the world supply of papayas. Etymology The word ''papaya'' comes from Arawak via Spanish, this is also where ''papaw'' and ''pawpaw'' come from. Description The papaya is a small, sparsely branched tree, usually with a single stem growing from tall, with spirally arranged leaves confined to the top of the trunk. The lower trunk is conspicuously scarred where leaves and fruit were borne. The leaves are large, in diameter, deeply palmately lobed, with seven lobes. All parts of the plant contain latex in articulated laticifers. Flowers Papayas are dioecious. The flowers are five-parted and highly dimorphic; the male flowers have the stamens fused to the petals. The female flowers h ...
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Glucotropaeolin
Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables, particularly garden cress. Upon enzymatic activity, it is transformed into benzyl isothiocyanate, which contributes to the characteristic flavor of these brassicas. Occurrence The compound was first reported in 1899, after its isolation from ''Tropaeolum majus'', a nasturtium species. Glucotropaeolin is now known to occur widely in other brassica, brassica families including Caricaceae, Phytolaccaceae, Resedaceae, Salvadoraceae and Tovariaceae. Structure The chemical structure of glucotropaeolin was confirmed by total synthesis in 1957. This showed that it is a glucose derivative with pyranose, β-D-glucopyranose configuration. At that time it was unclear whether the C=N bond was in the E–Z notation, Z form, with sulfur and oxygen substituents on the same side of the double bond, or the alternative E form in which they are on opposite sides. The suggestion was made that the Z form was mo ...
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Myrosinase
Myrosinase (, ''thioglucoside glucohydrolase'', ''sinigrinase'', and ''sinigrase'') is a family of enzymes involved in plant defense against herbivores, specifically the mustard oil bomb. The three-dimensional structure has been elucidated and is available in the PDB (see links in the infobox). A member of the glycoside hydrolase family, myrosinase possesses several similarities with the more ubiquitous O-glycosidases. However, myrosinase is the only known enzyme found in nature that can cleave a thio-linked glucose. Its known biological function is to catalyze the hydrolysis of a class of compounds called glucosinolates. Myrosinase activity Myrosinase is regarded as a defense-related enzyme and is capable of hydrolyzing glucosinolates into various compounds, some of which are toxic. Mechanism Myrosinase catalyzes the chemical reaction :a thioglucoside + H2O \rightleftharpoons a sugar + a thiol Thus, the two substrates of this enzyme are thioglucoside and H2O, whereas it ...
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Pancreatic
The pancreas is an Organ (anatomy), organ of the digestive system and endocrine system of vertebrates. In humans, it is located in the abdominal cavity, abdomen behind the stomach and functions as a gland. The pancreas is a mixed or heterocrine gland, i.e. it has both an endocrine and a digestive exocrine function. 99% of the pancreas is exocrine and 1% is endocrine. As an endocrine gland, it functions mostly to regulate blood sugar levels, secreting the hormones insulin, glucagon, somatostatin, and pancreatic polypeptide. As a part of the digestive system, it functions as an exocrine gland secreting pancreatic juice into the duodenum through the pancreatic duct. This juice contains bicarbonate, which neutralizes acid entering the duodenum from the stomach; and digestive enzymes, which break down carbohydrates, proteins, and lipids, fats in food entering the duodenum from the stomach. Inflammation of the pancreas is known as pancreatitis, with common causes including chronic Alc ...
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In Vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology and its subdisciplines are traditionally done in labware such as test tubes, flasks, Petri dishes, and microtiter plates. Studies conducted using components of an organism that have been isolated from their usual biological surroundings permit a more detailed or more convenient analysis than can be done with whole organisms; however, results obtained from ''in vitro'' experiments may not fully or accurately predict the effects on a whole organism. In contrast to ''in vitro'' experiments, ''in vivo'' studies are those conducted in living organisms, including humans, and whole plants. Definition ''In vitro'' ( la, in glass; often not italicized in English usage) studies are conducted using components of an organism that have been isolated fro ...
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Isothiocyanates
In organic chemistry, isothiocyanate is the functional group , formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also known as mustard oils. An artificial isothiocyanate, phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation. Cruciferous vegetables, such as bok choy, broccoli, cabbage, cauliflower, kale, and others, are rich sources of glucosinolate precursors of isothiocyanates. Although there has been some basic research on how isothiocyanates might exert biological effects ''in vivo'', there is no high-quality evidence to date for its efficacy against human diseases. Structure Typical bond angles for and linkages in aryl isothiocyanates are 165° and 177°, respectively. The and distances are 117 and 158 pms. Synthesis and reactions Iso ...
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