Names | |
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Preferred IUPAC name (6aS,11bR)-7,11b-Dihydroindeno[2,1-c][1]benzopyran-3,6a,9,10(6H)-tetrol | |
Other names Brasilin; Natural Red 24; CI 75280 | |
Identifiers | |
3D model (JSmol) | |
4198570 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.799 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C16H14O5 | |
Molar mass | 286.283 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Brazilin is a naturally occurring, homoisoflavonoid, red dye obtained from the wood of Paubrasilia echinata , Biancaea sappan , Caesalpinia violacea, and Haematoxylum brasiletto (also known as Natural Red 24 and CI 75280). [1] Brazilin has been used since at least the Middle Ages to dye fabric, and has been used to make paints and inks as well. The specific color produced by the pigment depends on its manner of preparation: in an acidic solution brazilin will appear yellow, but in an alkaline preparation it will appear red. Brazilin is closely related to the blue-black dye precursor hematoxylin, having one fewer hydroxyl group. Brazilein, the active dye agent, is an oxidized form of brazilin. [2] [1]
Brazilin is obtained from the wood of Paubrasilia echinata , Biancaea sappan (Sappanwood), Caesalpinia violacea, and Haematoxylum brasiletto . [1] The sappanwood is found in India, Malaysia, Indonesia and Sri Lanka, the latter being a major supplier of the wood to Europe during the early Middle Ages. Later, discovery of brazilwood (Paubrasilia echinata) in the new world led to its rise in popularity with the dye industry and eventually its over-exploitation. Brazilwood is now classified as an endangered species. [3]
There are many ways to extract and prepare brazilin. A common recipe, developed in the Middle Ages, is to first powder the brazilwood, turning it into sawdust. Then, the powder can be soaked in lye (which produces a deep, purplish red) or a hot solution of alum (which produces an orange-red color), either of which extracts the color better than plain water alone. To the lye extract, alum is added (or to the alum extract, lye) in order to fix the color, which will precipitate from the solution. The precipitate can be dried and powdered, and is a type of lake pigment.
Like many lake pigments, the exact colors produced depends on the pH of the mixture and the fixative used. Aluminium mordants used with brazilin produce the standard red colors, while the use of a tin mordant, in the form of SnCl
2 or SnCl
4 added to the extract is capable of yielding a pink color.
An alternative preparation which produces a transparent red color involves soaking the brazilwood powder in glair or a solution of gum arabic. Alum is added to help develop and fix the color, which can then be used as a transparent ink or paint.
As with hematein, brazilin can be used for staining cell nuclei in histological preparations when combined with aluminium. The nuclei are then colored red instead of blue.
A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.
Haematoxylin or hematoxylin, also called natural black 1 or C.I. 75290, is a compound extracted from heartwood of the logwood tree with a chemical formula of C
16H
14O
6. This naturally derived dye has been used as a histologic stain, as an ink and as a dye in the textile and leather industry. As a dye, haematoxylin has been called palo de Campeche, logwood extract, bluewood and blackwood. In histology, haematoxylin staining is commonly followed by counterstaining with eosin. When paired, this staining procedure is known as H&E staining and is one of the most commonly used combinations in histology. In addition to its use in the H&E stain, haematoxylin is also a component of the Papanicolaou stain which is widely used in the study of cytology specimens.
Alizarin is an organic compound with formula C
14H
8O
4 that has been used throughout history as a red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus. In 1869, it became the first natural dye to be produced synthetically.
A mordant or dye fixative is a substance used to set dyes on fabrics. It does this by forming a coordination complex with the dye, which then attaches to the fabric. It may be used for dyeing fabrics or for intensifying stains in cell or tissue preparations. Although mordants are still used, especially by small batch dyers, they have been largely displaced in industry by directs.
Carmine – also called cochineal, 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.
Paubrasilia echinata is a species of flowering plant in the legume family, Fabaceae, that is endemic to the Atlantic Forest of Brazil. It is a Brazilian timber tree commonly known as Pernambuco wood or brazilwood and is the national tree of Brazil. This plant has a dense, orange-red heartwood that takes a high shine, and it is the premier wood used for making bows for stringed instruments. The wood also yields a historically important red dye called brazilin, which oxidizes to brazilein.
Staining is a technique used to enhance contrast in samples, generally at the microscopic level. Stains and dyes are frequently used in histology, in cytology, and in the medical fields of histopathology, hematology, and cytopathology that focus on the study and diagnoses of diseases at the microscopic level. Stains may be used to define biological tissues, cell populations, or organelles within individual cells.
Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).
Potassium bitartrate, also known as potassium hydrogen tartrate, with formula KC4H5O6, is a chemical compound with a number of uses. It is the potassium acid salt of tartaric acid (a carboxylic acid). In cooking, it is known as cream of tartar.
Aluminium sulfate is a salt with the formula Al2(SO4)3. It is soluble in water and is mainly used as a coagulating agent (promoting particle collision by neutralizing charge) in the purification of drinking water and wastewater treatment plants, and also in paper manufacturing.
Biancaea sappan is a species of flowering tree in the legume family, Fabaceae, that is native to tropical Asia. Common names in English include sappanwood and Indian redwood. It was previously ascribed to the genus Caesalpinia. Sappanwood is related to brazilwood, and was itself called brasilwood in the Middle Ages.
Hematein or haematein is an oxidized derivative of haematoxylin, used in staining. Haematein should not be confused with haematin, which is a brown to black iron-containing pigment formed by decomposition of haemoglobin. In the Colour Index, haematein is called haematine.
Orcein, also archil, orchil, lacmus and C.I. Natural Red 28, are names for dyes extracted from several species of lichen, commonly known as "orchella weeds", found in various parts of the world. A major source is the archil lichen, Roccella tinctoria. Orcinol is extracted from such lichens. It is then converted to orcein by ammonia and air. In traditional dye-making methods, urine was used as the ammonia source. If the conversion is carried out in the presence of potassium carbonate, calcium hydroxide, and calcium sulfate, the result is litmus, a more complex molecule. The manufacture was described by Cocq in 1812 and in the UK in 1874. Edmund Roberts noted orchilla as a principal export of the Cape Verde islands, superior to the same kind of "moss" found in Italy or the Canary Islands, that in 1832 was yielding an annual revenue of $200,000. Commercial archil is either a powder or a paste. It is red in acidic pH and blue in alkaline pH.
Hematoxylin and eosin stain is one of the principal tissue stains used in histology. It is the most widely used stain in medical diagnosis and is often the gold standard. For example, when a pathologist looks at a biopsy of a suspected cancer, the histological section is likely to be stained with H&E.
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 and the Palestine oak.
The cochineal is a scale insect in the suborder Sternorrhyncha, from which the natural dye carmine is derived. A primarily sessile parasite native to tropical and subtropical South America through North America, this insect lives on cacti in the genus Opuntia, feeding on plant moisture and nutrients. The insects are found on the pads of prickly pear cacti, collected by brushing them off the plants, and dried.
Stil de grain yellow or sap green is a pigment derived from berries of the buckthorn species Rhamnus saxatilis, which are commonly called Avignon berries or Persian berries after two historical areas of supply; latterly Italy was a major source. The color, whose principal chemical component is rhamnetin, was formerly called pink ; latterly, to distinguish it from light red "pink", the yellow "pink" was qualified as Dutch pink, brown pink, English pink, Italian pink, or French pink — the first three also applied to similar quercitron dyes from the American eastern black oak, Quercus velutina. Other names are Persian berries lake, yellow berries and buckthorn berries.
Natural dyes are dyes or colorants derived from plants, invertebrates, or minerals. The majority of natural dyes are vegetable dyes from plant sources—roots, berries, bark, leaves, and wood—and other biological sources such as fungi.
Dyeing is the craft of imparting colors to textiles in loose fiber, yarn, cloth or garment form by treatment with a dye. Archaeologists have found evidence of textile dyeing with natural dyes dating back to the Neolithic period. In China, dyeing with plants, barks and insects has been traced back more than 5,000 years. Natural insect dyes such as Tyrian purple and kermes and plant-based dyes such as woad, indigo and madder were important elements of the economies of Asia and Europe until the discovery of man-made synthetic dyes in the mid-19th century. Synthetic dyes quickly superseded natural dyes for the large-scale commercial textile production enabled by the Industrial Revolution, but natural dyes remained in use by traditional cultures around the world.
Haematoxylum brasiletto, or Mexican logwood, is a species of tropical hardwood tree in the legume family, Fabaceae. It is known in its native Mexico and Guatemala as "palo de brasil" or "palo de tinto". The timber is used to make bows for stringed instruments, the manufacture of dyes and in ethnobotany.
This article includes a list of references, related reading, or external links, but its sources remain unclear because it lacks inline citations .(September 2012) |