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Names | |
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IUPAC name 7-[5-(2-acetamidoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid | |
Other names Red lac, Shellac, Lac dye | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
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Properties | |
C26H19NO12 | |
Molar mass | 537.44 g·mol−1 |
Density | 1.7±0.1 g.cm3 |
Vapor pressure | 0.0±0.3 mmHg at 25°C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [1] This article focuses primarily on laccaic acid A (LCA). [2] [3]
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.
Laccaic acids are mainly used to dye natural fabrics (mostly silk, wool, or cotton) and food, including both drinks and solid products. [4] 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 silk and wool. It is a similar color to dyes obtained from cochineals and kermes. The color of the dye can be modified by the choice of mordant from violet to red to brown. The use of lac dye can be traced back to 250 AD when it was mentioned by Claudius Aelianus, a Roman writer on a volume about natural history. This pigment made from lac dye, Indian Lake, was listed by Winsor & Newton in their 1896 catalogue.
These derivatives differ through one ramification except for the acid D, which is closer in form to the kermesic acid. Acid laccaic D can be confused or interchanged with flavokermisic acid due to their almost identical structure. [5] These acids can all be represented in a general form (lac-dye), where the derivative A is the most important.
The different derivatives include:
Acid B (3,5,6,8-tetrahydroxy-7-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-9,10-dioxoanthracene-1,2-dicarboxylic acid) [6]
Acid C (7-[5-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid) [7]
Acid D (3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid) [8]
Acid E (7-[5-(2-aminoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid) [9]
Laccaic acids | |||||
Name | Laccaic acid A | Laccaic acid B | Laccaic acid C | Laccaic acid D | Laccaic acid E |
Structure | |||||
Molecular formula | C26H19NO12 | C24H16O12 | C25H17NO13 | C16H10O7 | C24H17NO11 |
Molecular weight | 537.44 g/mol | 496.38 g/mol | 539.41 g/mol | 314.25 g/mol | 495.40 g/mol |
CAS number | 15979-35-8 | 17249-00-2 | 23241-56-7 | 18499-84-8 | 14597-16-1 |
60687-93-6 (A-E mix) |
Laccaic acid A has an amide functional group in its structure while the acids B, C, and E have amine groups. [10] The only difference between the acid D and kermesic acid is a hydroxide function missing on the position 8.
Acids A, B, C, and E can be isolated from lac dye through many different ways: microwave induced from lac insects, high speed counter-current chromatography or liquid chromatography-mass spectrometry. [11] [12] [13]
The stick lac collected from Rain trees (mostly located in Asia) can be powdered in a mill and finely ground. The powdered material is extracted with deionized water at 60°C for 1 h. The aqueous solution is filtered and then concentrated under reduced pressure in a rotary evaporator to give a crude lac dye extract, which can then be used without further purification. This extract can be directly named lac dye. [14]
Grind the body with the appropriate amount of water, then use 4-5 times the original amount of water for extraction several times. Centrifuge to remove all slag, then add a small amount of sodium hydroxide and calcium chloride solution to the extract, then add dilute chloric acid. The pH slowly adjusts to 2.1. Let stand for 3-4 hours, clean and filter. Concentrated sulfuric acid is added to the filtrate until the pigment crystals precipitate, filtered through spun silk (~0.12 mm), the filtrate is allowed to stand for 1-2 days, and then the pigment crystals are precipitated, filtered and washed 3 times by water , dried crush and sift at 60 °C, resulting in a final product with a degree of separation of ~0.8%.
After the dye washing of the wastewater from the shellac cleaning, the pH value of the solution is adjusted to 4.0-4.5 with dilute hydrochloric acid. The supernatant is taken for filtration after standing for 4 hours, the pH of the filtrate is adjusted to 5.5-6.0 with a dilute alkaline solution, then a saturated calcium chloride solution is added to precipitate calcium-lac acid. After 8 hours of clarification . The supernatant is removed, the precipitate is filtered, after filtration, concentrated hydrochloric acid is added, washed with water until the acid is no longer present, and dried to obtain the final lac red pigment. [15]
DNMT1 is inhibited by LCA which has a stronger inhibitory effect than SG-1027 (HY-13962). LCA is a class of DNMT inhibitors may be a useful mechanism to inhibit DNMT. [16]
As a major component of lac dye, LCA is usually chosen as a representative for the lac dye to describe their thermodynamics properties including adsorption, dyeability, fastness and shade variation of lac dyeing on silk and cotton. Studies indicate that the intermolecular interactions between LCA and fibers as well as between LCA and mordants play a key role on the adsorption and dyeability of lac dye [17] [18]
Lac extract produces purple colors from burgundy to deep purple. The colors are similar to cochineal colors, but warmer, softer and more muted. Lac paint has high light and washing fastness on silk and wool. Only small amounts are needed for medium depth shade. Lac is not so fast in cellulose fibers (plant fibers). Lac is very sensitive to pH, increasing alkalinity will turn the colors plummy purple, while acidity will give bright oranges. However, colors that have been altered by the pH change may turn red again after washing.
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.
A lake pigment is a pigment made by precipitating a dye with an inert binder, or mordant, usually a metallic salt. Unlike vermilion, ultramarine, and other pigments made from ground minerals, lake pigments are organic. Manufacturers and suppliers to artists and industry frequently omit the lake designation in the name. Many lake pigments are fugitive because the dyes involved are not lightfast. Red lakes were particularly important in Renaissance and Baroque paintings; they were often used as translucent glazes to portray the colors of rich fabrics and draperies.
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.
Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis, ampyrone itself has significantly lower toxicity. It is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates liver microsomes and is also used to measure extracellular water.
5,12-Bis(phenylethynyl)naphthacene is a fluorescent dye used in lightsticks. It yields orange light.
Triethylammonium acetate is a volatile salt, which is often used as an ion-pairing reagent in high-performance liquid chromatography separations of oligonucleotides. Since unadjusted triethylammonium acetate salt solutions contain neither a conjugate acid nor a conjugate base, they are not buffers.
Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.
Fluorenol, also known as hydrafinil, is an alcohol derivative of fluorene. In the most significant isomer, fluoren-9-ol or 9-hydroxyfluorene, the hydroxy group is located on the bridging carbon between the two benzene rings. Hydroxyfluorene can be converted to fluorenone by oxidation. It is a white-cream colored solid at room temperature.
2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.
Acetoxolone is a drug used for peptic ulcer and gastroesophageal reflux disease. It is an acetyl derivative of glycyrrhetinic acid. It is found in Echinopora lamellosa.
Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V-sub x and GD-7.
In chemistry, methanetetracarboxylate is a tetravalent anion with formula C5O4−8 or C(−CO−2)4. It has four carboxylate groups attached to a central carbon atom; so it has the same carbon backbone as neopentane. It is an oxocarbon anion, that is, consists only of carbon and oxygen.
Anthraquinone dyes are an abundant group of dyes comprising a anthraquinone unit as the shared structural element. Anthraquinone itself is colourless, but red to blue dyes are obtained by introducing electron donor groups such as hydroxy or amino groups in the 1-, 4-, 5- or 8-position. Anthraquinone dyestuffs are structurally related to indigo dyestuffs and are classified together with these in the group of carbonyl dyes.
Neoendorphins are a group of endogenous opioid peptides derived from the proteolytic cleavage of prodynorphin. They include α-neoendorphin and β-neoendorphin. The α-neoendorphin is present in greater amounts in the brain than β-neoendorphin. Both are products of the dynorphin gene, which also expresses dynorphin A, dynorphin A-(1-8), and dynorphin B. These opioid neurotransmitters are especially active in Central Nervous System receptors, whose primary function is pain sensation. These peptides all have the consensus amino acid sequence of Try-Gly-Gly-Phe-Met (met-enkephalin) or Tyr-Gly-Gly-Phe-Leu ( leu-enkephalin). Binding of neoendorphins to opioid receptors (OPR), in the dorsal root ganglion (DRG) neurons results in the reduction of time of calcium-dependent action potential. The α-neoendorphins bind OPRD1(delta), OPRK1(kappa), and OPRM1 (mu) and β-neoendorphin bind OPRK1.
Isoxerocomic acid is a red-orange pigment found in Boletales. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. It is the isomer of xerocomic acid and precursor to xerocomorubin.
A dibromoanthracene is a derivative of anthracene with two bromine atoms. All compounds have the formula C14H8Br2. They are all isomers of one another.
Butoxyacetic acid is an aliphatic organic chemical. It is a liquid. It has the formula C6H12O3 and CAS Registry Number of 2516-93-0. It is REACH registered with the EC number 677-344-8. n-Butyl glycidyl ether is metabolized renally to this compound as is 2-butoxyethanol. Methods have been developed and papers published to detect the compound in urine and blood.
Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate (INCI) is an organic compound used in sunscreens to absorb UVA radiation. It is marketed as Mexoryl 400 by L'Oréal. MCE has an absorption maximum of 385 nm, which is in the long-wave UVA range. Like Mexoryl SX (Ecamsule) and Mexoryl XL, it is used exclusively in products manufactured by L'Oréal. MCE was developed by L'Oréal and BASF.
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