Kermesic Acid
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Kermesic Acid
Kermesic acid is an anthraquinone derivative and the main component of the red dye kermes (false carmine). The compound is the aglycone of carminic acid, the main component of true carmine. As a dye, it is known as Natural Red 3. Kermesic acid, like carminic acid and the laccaic acids, is an insect dye obtained from scale insects. Kermesic acid is found in insects of the genus '' Kermes''. It is the only colored component of the dye kermes. The chemical structure of kermesic acid was elucidated by Otto Dimroth Otto Dimroth (28 March 1872 – 16 May 1940) was a German chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist trained in the study of chemistry. Chemists study the comp ... in 1916. References Anthraquinones Carboxylic acids {{Chem-stub ...
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Kermes (dye)
Kermes is a red dye derived from the dried bodies of the females of a scale insect in the genus '' Kermes'', primarily ''Kermes vermilio''. The ''Kermes'' insects are native in the Mediterranean region and are parasites living on the sap of the host plant, the Kermes oak (''Quercus coccifera'') and the Palestine oak (''Quercus calliprinos'').Amar, ''et al''. (2005), p. 1081 These insects were used as a red dye since antiquity by the ancient Egyptians, Mesopotamians, Indians, Greeks, Romans, and Iranians. The kermes dye is a rich red, a crimson. It has good colour fastness in silk and wool. It was much esteemed in the medieval era for dyeing silk and wool, particularly scarlet cloth. Post-medievally it was replaced by other red dyes, starting with cochineal. Etymology Kermes ultimately derives from the Sanskrit word कृमिज or ''kṛmija'' meaning "worm-made". This was adopted into Persian and later Arabic as قرمز ''qermez''. The modern English word kermes was borro ...
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Aglycone
An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone. Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate and detect them at a sensitivity of 0.25-0.50 µg. Clinical significance A study on molecular markers in human aortic endothelial cells published that aglycone stopped cell migration but not monocyte adhesion, which is the initial step of atherosclerotic plaq ...
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Carminic Acid
Carminic acid (C22H20O13) is a red glucosidal hydroxyanthrapurin that occurs naturally in some scale insects, such as the cochineal, Armenian cochineal, and Polish cochineal. The insects produce the acid as a deterrent to predators. An aluminum salt of carminic acid is the coloring agent in carmine, a pigment. Natives of Peru had been producing cochineal dyes for textiles since at least 700 CE. Synonyms are C.I. 75470 and C.I. Natural Red 4. The chemical structure of carminic acid consists of a core anthraquinone structure linked to a glucose sugar unit. Carminic acid was first synthesized in the laboratory by organic chemists in 1991. In 2018, researchers genetically engineered the microbe ''Aspergillus nidulans'' to produce carminic acid. It was previously thought that it contains α-D-glucopyranosyl residue, which was later redetermined to be the β-D-glucopyranosyl anomer. Harvesting from cochineals Carminic acid is commonly harvested from an American species scal ...
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Carmine
Carmine ()also called cochineal (when it is extracted from the cochineal insect), cochineal extract, crimson lake, or carmine lake is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. ''Carmine'' is also a general term for a particularly deep-red color. Etymology The English word "carmine" is derived from the French word ''carmin'' (12th century), from Medieval Latin ''carminium'', from Persian ''qirmiz'' ("crimson"), which itself derives from Middle Persian ''carmir'' ("red, crimson"). The Persian term ''carmir'' is likely cognate with Sanskrit ''krimiga'' ("insect-produced"), from ''krmi'' ("worm, insect"). The Persian word for "worm, insect" is ''kirm'', and in Iran (Persia) the red colorant carmine was extracted from the bodies of dead female insects such as ''Kermes vermilio'' and cochineal. The form of the term may also have been influen ...
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Laccaic Acid
Laccaic acids or laccainic acids are a group of five anthraquinone derivatives, designated A through E, which are components of the red shellac obtained from the insect '' Kerria lacca'', similar to carminic acid and kermesic acid. This article focuses primarily on laccaic acid A (LCA). History   Etymology The word varnish goes back to the old Indian Sanskrit word laksha, meaning a hundred thousand lice, and came into German via the Italian “lacca” in the 16th century. The word also exists in Hindi (Lakh) and Sinhala (Lakda). The term Lac Dye comes from English "dye" means paint dye. This pigment is mostly found in South and South-East Asia. Usage Laccaic acids are mainly used to dye natural fabrics (mostly silk, wool, or cotton) and food, including both drinks and solid products. It is one of the most common natural dyes, but it is less used in cosmetics than carmine, the main natural dye used in this industry.  The bright red colorant gives a lightfast tint to ...
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Scale Insect
Scale insects are small insects of the order Hemiptera, suborder Sternorrhyncha. Of dramatically variable appearance and extreme sexual dimorphism, they comprise the infraorder Coccomorpha which is considered a more convenient grouping than the superfamily Coccoidea due to taxonomic uncertainties. Adult females typically have soft bodies and no limbs, and are concealed underneath domed scales, extruding quantities of wax for protection. Some species are hermaphroditic, with a combined ovotestis instead of separate ovaries and testes. Males, in the species where they occur, have legs and sometimes wings, and resemble small flies. Scale insects are herbivores, piercing plant tissues with their mouthparts and remaining in one place, feeding on sap. The excess fluid they imbibe is secreted as honeydew on which sooty mold tends to grow. The insects often have a mutualistic relationship with ants, which feed on the honeydew and protect them from predators. There are about 8,000 descr ...
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Kermes (insect)
''Kermes'' is a genus of scale insects in the order Hemiptera. They feed on the sap of evergreen oaks; the females produce a red dye, also called "Kermes (dye), kermes", that is the source of natural crimson. The word "kermes" is derived from Persian or Turkish ''qirmiz'' or ''kirmizi'' (wikt:قرمز, قرمز), "crimson" (both the colour and the dyestuff). There are some 20 species, including: * ''Kermes bacciformis'' Leonardi, 1908 * ''Kermes corticalis'' (Nassonov, 1908) * ''Kermes echinatus'' (Balachowsky, 1953) * ''Kermes gibbosus'' Signoret, 1875 * ''Kermes ilicis'' (Linnaeus, 1758) * ''Kermes roboris'' (Fourcroy, 1785) * ''Kermes vermilio'' Planchon, 1864 References External links Conservation and Art Material Encyclopedia Online
Kermesidae Sternorrhyncha genera {{Coccoidea-stub ...
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Otto Dimroth
Otto Dimroth (28 March 1872 – 16 May 1940) was a German chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties. Chemists carefully describe t .... He is known for the Dimroth rearrangement, as well as a type of condenser with an internal double spiral, the Dimroth condenser. His son Karl Dimroth was also a renowned chemist, who described the first synthesis of 3-benzoxepin. References * Academic staff of the University of Greifswald 1872 births 1940 deaths {{germany-scientist-stub ...
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Anthraquinones
''For the parent molecule 9,10-anthraquinone, see anthraquinone'' Anthraquinones (also known as anthraquinonoids) are a class of naturally occurring phenolic compounds based on the 9,10-anthraquinone skeleton. They are widely used industrially and occur naturally. Occurrence in plants : Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and cascara buckthorn, fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ..., lichens, and some insects. A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium ''Photorhabdus luminescens''. Chorismate, formed by isochorismate synthase in the shikimate pathway, is a precursor of anthraquinones in ''Morinda citrifolia''. Tests for anthraquinones in ...
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