Ruberythric acidCAS# 152-84-1 |
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| Cas No. | 152-84-1 | SDF | Download SDF |
| PubChem ID | 92101 | Appearance | Yellow powder |
| Formula | C25H26O13 | M.Wt | 534.5 |
| Type of Compound | Anthraquinones | Storage | Desiccate at -20°C |
| Synonyms | Alizarin 2-β-primeveroside; Rubianic acid; Rubierythric acid | ||
| Solubility | Soluble in methanol; sparingly soluble in water | ||
| Chemical Name | 1-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-9,10-dione | ||
| SMILES | C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C4=C(C=C3)C(=O)C5=CC=CC=C5C4=O)O)O)O)O)O)O)O | ||
| Standard InChIKey | GCGGSVAWTYHZBI-CVQRFVFPSA-N | ||
| Standard InChI | InChI=1S/C25H26O13/c26-12-7-35-24(22(33)18(12)29)36-8-14-20(31)21(32)23(34)25(38-14)37-13-6-5-11-15(19(13)30)17(28)10-4-2-1-3-9(10)16(11)27/h1-6,12,14,18,20-26,29-34H,7-8H2/t12-,14-,18+,20-,21+,22-,23-,24+,25-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Ruberythric acid Dilution Calculator
Ruberythric acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.8709 mL | 9.3545 mL | 18.7091 mL | 37.4181 mL | 46.7727 mL |
| 5 mM | 0.3742 mL | 1.8709 mL | 3.7418 mL | 7.4836 mL | 9.3545 mL |
| 10 mM | 0.1871 mL | 0.9355 mL | 1.8709 mL | 3.7418 mL | 4.6773 mL |
| 50 mM | 0.0374 mL | 0.1871 mL | 0.3742 mL | 0.7484 mL | 0.9355 mL |
| 100 mM | 0.0187 mL | 0.0935 mL | 0.1871 mL | 0.3742 mL | 0.4677 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Mild extraction methods using aqueous glucose solution for the analysis of natural dyes in textile artefacts dyed with Dyer's madder (Rubia tinctorum L.).[Pubmed:28131591]
J Chromatogr A. 2017 Mar 3;1487:36-46.
Madder (Rubia tinctorum L.) has been widely used as a red dye throughout history. Acid-sensitive colorants present in madder, such as glycosides (lucidin primeveroside, Ruberythric acid, galiosin) and sensitive aglycons (lucidin), are degraded in the textile back extraction process; in previous literature these sensitive molecules are either absent or present in only low concentrations due to the use of acid in typical textile back extraction processes. Anthraquinone aglycons alizarin and purpurin are usually identified in analysis following harsh back extraction methods, such those using solvent mixtures with concentrated hydrochloric acid at high temperatures. Use of softer extraction techniques potentially allows for dye components present in madder to be extracted without degradation, which can potentially provide more information about the original dye profile, which varies significantly between madder varieties, species and dyeing technique. Herein, a softer extraction method involving aqueous glucose solution was developed and compared to other back extraction techniques on wool dyed with root extract from different varieties of Rubia tinctorum. Efficiencies of the extraction methods were analysed by HPLC coupled with diode array detection. Acidic literature methods were evaluated and they generally caused hydrolysis and degradation of the dye components, with alizarin, lucidin, and purpurin being the main compounds extracted. In contrast, extraction in aqueous glucose solution provides a highly effective method for extraction of madder dyed wool and is shown to efficiently extract lucidin primeveroside and Ruberythric acid without causing hydrolysis and also extract aglycons that are present due to hydrolysis during processing of the plant material. Glucose solution is a favourable extraction medium due to its ability to form extensive hydrogen bonding with glycosides present in madder, and displace them from the fibre. This new glucose method offers an efficient process that preserves these sensitive molecules and is a step-change in analysis of madder dyed textiles as it can provide further information about historical dye preparation and dyeing processes that current methods cannot. The method also efficiently extracts glycosides in artificially aged samples, making it applicable for museum textile artefacts.
Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation.[Pubmed:26091962]
Phytochemistry. 2015 Sep;117:168-173.
Madder (Rubia tinctorum L.) has been exploited as a dye throughout history. The roots of the plant are very rich in the highly coloured glycosidic compounds Ruberythric acid and lucidin primeveroside, alongside the corresponding aglycons which can be readily formed by deglycosylation, particularly during extraction. Supported by (1)H and (13)C NMR data, the conclusive X-ray crystal structure of the natural dye Ruberythric acid is presented for the first time. The solid state structure revealed extensive intermolecular hydrogen bonding interactions between the sugar moieties in the unit cell, but only intramolecular hydrogen bonding through the hydroxyquinone groups. There is also some additional pi-pi stacking from the anthraquinone moiety.
Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation.[Pubmed:23891215]
Phytochemistry. 2013 Nov;95:105-8.
Madder (Rubia tinctorum L.) has been used as a dye for over 2000 years with alizarin and purpurin the major natural dyes analysed from extractions undertaken. The use of ethanol as the solvent in the extraction process produced an extract that yielded four anthraquinone compounds lucidin primeveroside, Ruberythric acid, alizarin and lucidin-omega-ethyl ether. Gravitational separation of the extract was used to record the first crystal structure of lucidin primeveroside, which is also the first ever known crystal structure of a glycoside containing anthraquinone moiety. The crystal structure along with (1)H and (13)C NMR helped elucidate and confirm the structure of this overlooked natural dye which has been shown to be a major compound in R. tinctorum L.
A multivariate study of the performance of an ultrasound-assisted madder dyes extraction and characterization by liquid chromatography-photodiode array detection.[Pubmed:18617432]
Ultrason Sonochem. 2009 Jan;16(1):75-82.
An extraction method of madder (Rubia tinctorum) roots dyes is established and optimized to obtain the original chemical composition. A central composite design (CCD) was developed to specify the importance of the three major factors studied (time, temperature and solvent composition) affecting the ultrasound-assisted extraction of this matrix. A preliminary granulometric study of madder roots is realized in the aim to determine the optimal particles size corresponding to the best ultrasound effects. A comparison with the classical extraction method of madder dyes by reflux is described. The identification of the constituents of R. tinctorum is carried out by liquid chromatography coupled with a photodiode array detector (LC-PDA). Anthraquinonic aglycone and heterosidic dyes compounds are characterized by retention time and UV spectrum: alizarin (1,2-dihydroxyanthraquinone), purpurin (1,2,4-trihydroxyanthraquinone), lucidin (1,3-dihydroxy-2-hydroxymethylanthraquinone), rubiadin (1,3-dihydroxy-2-methylanthraquinone), xanthopurpurin (1,3-dihydroxyanthraquinone), pseudopurpurin (1,2,4-trihydroxy-3-carboxyanthraquinone), lucidin primeveroside, Ruberythric acid (alizarin primeveroside), galiosin (pseudopurpurin primeveroside) and rubiadin primeveroside. The optimal experimental conditions are 18min, 36 degrees C and 37/63 MeOH/H(2)O (v/v).
Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars.[Pubmed:15599964]
Phytochem Anal. 2004 Nov-Dec;15(6):397-406.
Direct and indirect HPLC-UV methods for the quantitative determination of anthraquinones in dried madder root have been developed, validated and compared. In the direct method, madder root was extracted twice with refluxing ethanol-water. This method allowed the determination of the two major native anthraquinone glycosides lucidin primeveroside and Ruberythric acid. In the indirect extraction method, the anthraquinone glycosides were first converted into aglycones by endogenous enzymes and the aglycones were subsequently extracted with tetrahydrofuran-water and then analysed. In this case the anthraquinones alizarin, purpurin and nordamnacanthal may be determined. The content of nordamnacanthal is proportional to the amount of lucidin primeveroside originally present. The indirect extraction method is easier to apply. Different madder cultivars were screened for their anthraquinone content.
Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots.[Pubmed:12793459]
Phytochem Anal. 2003 May-Jun;14(3):137-44.
For the production of a commercially useful dye extract from madder, the glycoside Ruberythric acid has to be hydrolysed to the aglycone alizarin which is the main dye component. An intrinsic problem is the simultaneous hydrolysis of the glycoside lucidin primeveroside to the unwanted mutagenic aglycone lucidin. Madder root was treated with strong acid, strong base or enzymes to convert Ruberythric acid into alizarin and the anthraquinone compositions of the suspensions were analysed by HPLC. A cheap and easy method to hydrolyse Ruberythric acid in madder root to alizarin without the formation of lucidin turned out to be the stirring of dried madder roots in water at room temperature for 90 min: this gave a suspension containing pseudopurpurin, munjistin, alizarin and nordamnacanthal. Native enzymes are responsible for the hydrolysis, after which lucidin is converted to nordamnacanthal by an endogenous oxidase.
