478-08-0

Basic information

• Product Name: LUCIDIN
• Synonyms: 1,3-dihydroxy-2-(hydroxymethyl)-10-anthracenedione;1,3-dihydroxy-2-hydroxymethylanthraquinoline;1,3-dihydroxy-2-hydroxymethyl-anthraquinon;henine;1,3-DIHYDROXY-2-(HYDROXYMETHYL)ANTHRAQUINONE;LUCIDIN;1,3-Dihydroxy-2-hydroxymethylanthracene-9,10-dione;Lucidin【quinone】
• CAS NO: 478-08-0
• Molecular Formula: C15H10O5
• Molecular Weight: 270.24
• Product Categories: Anthraquinones
• Mol File: 478-08-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: >330℃
• Boiling Point: 333.35°C (rough estimate)
• Flash Point: 321.6°C
• Appearance: /
• Density: 1.592±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.57E-14mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO
• PKA: 6.83±0.20(Predicted)
• CAS DataBase Reference: LUCIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: LUCIDIN(478-08-0)
• EPA Substance Registry System: LUCIDIN(478-08-0)

Safety Data

• Hazardous Substances Data: 478-08-0(Hazardous Substances Data)

Usage

Biological Activity

lucidin (nsc 30546) is a natural component of rubia tinctorum l., which is mutagenic in bacteria and mammalian cells [1].hydroxyanthraquinones (has) are special organic compounds widely distributed in the plant kingdom. the ha plants have been used as laxatives and colorant for thousands of years. in the last century, has were also employed as medicine for the treatment of kidney stone. lucidin is a ha extracted from the root of rubia tinctorum l. that also known as madder. it was thought to be genotoxic in bacteria and mammalian cells [1].lucidin was found to be mutagenic in five salmonella typhimurium strains without metabolic activation. additionally, in chinese hamster fibroblast v79 cells, lucidin was found to be mutagenic at the hypoxanthine-guanine phosphoribosyl transferase gene locus, which induced dna single-strand breaks and dna-protein cross-link. in primary rat hepatocytes and transformed c3h/ m2-mouse fibroblasts, it was observed lucidin might induce dna repair synthesis [1].in mouse model, when aci rats were treated with 1-10% madder roots in the diet and control group without madder roots for 780 days, the dose-dependent increase of benign and malignant tumors were observed in liver and kidney. additionally, dna adducts were observed in liver, kidney and colon when treated with 10% madder root for two weeks. the formation of dna adducts and mutagenicity was thought to be associated with lucidin which was contained in the madder roots [2].

references

[1] westendorf j et al. , the genotoxicity of lucidin, a natural component of rubia tinctorum l., and lucidinethylether, a component of ethanolic rubia extracts. cell biol toxicol. 1988, 4(2):225-239.[2] westendorf j et al. , carcinogenicity and dna adduct formation observed in aci rats after long-term treatment with madder root, rubia tinctorum l. carcinogenesis. 1998, 19(12):2163-2168.

InChI:InChI=1/C15H10O5/c16-6-10-11(17)5-9-12(15(10)20)14(19)8-4-2-1-3-7(8)13(9)18/h1-5,16-17,20H,6H2

Upstream product

• 50-00-0 formaldehyd 
• 518-83-2 xanthopurpurin 
• 108-46-3 recorcinol 
• 85-44-9 phthalic anhydride 
• 29706-59-0 lucidin primeveroside 
• 22255-29-4 1-Hydroxy-2-hydroxymethyl-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-anthraquinone 
• 29706-59-0 lucidin-3-primeveroside 
• 859781-39-8 1,3-diacetoxy-2-bromomethyl-anthraquinone 

Downstream Products

• 3736-59-2 nordamnacanthal 
• 61434-48-8 lucidin dimethyl ether 
• 184916-38-9 1-hydroxy-2-(hydroxymethyl)-3-methoxyanthraquinone 
• 518-83-2 xanthopurpurin 
• 79560-36-4 1,3-dihydroxy-2-methoxymethylanthraquinone 
• 477-83-8 damnacanthol 
• 124245-03-0 1,3-bis-benzoyloxy-2-benzoyloxymethyl-anthraquinone 

Relevant articles and documents

Degradation of lucidin: New insights into the fate of this natural pigment present in Dyer's madder (Rubia tinctorum L.) during the extraction of textile artefacts

The complex mixtures of colorants present in different madder species can provide significant information about which plant species or technique was used to dye the fibres of historical textile artefacts, hence, when extracting and analysing colorants from textile artefacts as much of this information as possible should be preserved. Historical textiles are most commonly extracted with 37% hydrochloric acid: methanol: water (2:1:1, v/v/v), but this solvent system hydrolyses dye glycosides and may also induce chemical reactions. One of the primary components in Dyers’ madder (Rubia tinctorum L.) is lucidin primeveroside, but it is rarely seen in artefacts, nor is the corresponding aglycon lucidin. It has been demonstrated that the hydrochloric acid method causes hydrolysis of anthraquinone glycosides to their aglycon counterpart. Herein it is demonstrated that lucidin is not stable in such acidic conditions and degrades rapidly to xanthopurpurin. This is confirmed by HPLC, LC-MS and 1H NMR, which also provide evidence of the mechanism of degradation being a retro-aldol process.

Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F.

The insect antifeedant anthraquinone aldehyde nordamnacanthal (1,3-dihydroxy-anthraquinone-2-al) was identified in Galium aparine L., and isolated from the root powder of akane (Rubia akane), a member of the Rubiaceae. Structure-activity relationship (SAR) studies using a series of anthraquinone analogues suggested that the aldehyde group on the anthraquinone was more important than the quinone moiety for antifeedant activity against the common cutworm (Spodoptera litura). High levels of nordamnacanthal were found in the seed leaf stage and in callus tissue induced from seedlings of G. aparine, but its concentration decreased with plant development. Since these compounds are natural pigments for dying textiles, we also evaluated the antifeedant activity against the carpet beetle (Attagenus japonicus), a textile pest was also evaluated. While nordamnacanthal had strong antifeedant activity against the common cutworm, it did not show any antifeedant activity against the carpet beetle. The most effective antifeedant against the carpet beetle was the major constituent in the extract of R. trictorum, lucidin- 3 - O-primeveroside, a food pigment. 2002 Elsevier Science Ltd. All rights reserved.

BIOSYNTHESIS OF ANTHRAQUINONES AND RELATED COMPOUNDS IN GALIUM MOLLUGO CELL SUSPENSION CULTURES

From Galium mollugo cell suspension cultures, 1,4-dihydroxy-3-prenyl-2-naphtholic acid methyl ester diglucoside was isolated along with anthraquinones and mollugin.Production of the diglucoside was much increased by administering 2-succinylbenzoate to the cultures.The incorporation of 2-succinylbenzoate into lucidin-3-primeveroside, mollugin and the diglucoside in the mode so far proposed for rubiaceous anthraquinones was verified by administration of 13C-labelled 2-succinylbenzoate to the cell cultures.Key Word Index - Galium mollugo; Rubiaceae; lucidin-3-primeveroside; 1,4-dihydroxy-3-prenyl-2-naphthoic acid methyl ester diglucoside; biosynthesis; cell suspension culture; 13C NMR; mass spectrometry.