colorant
Alizarin
Also known as: alizarin
A red anthraquinone colourant found in the roots of madder (Rubia) and related plants, reported to be 1,2-dihydroxyanthraquinone. It forms complexes with metals such as aluminium, and with an alum mordant it gives a bright yellowish red.
Theme: Held by metal
Claims and evidence (23)
The limitations noted for some sources are recorded in Japanese only — see the Japanese edition.
Alizarin differs from Purpurincontextual
Scope: Compares with present-day alum-mordanted Western-madder dyeing; concerns this one Coptic-tapestry sample.
States that the alizarin:purpurin ratio is about 7:3 in extracts from present-day alum-mordanted Western-madder dyeing, but about 1:9 -- with extremely low alizarin -- in this Coptic tapestry.
Source: 科学の眼で文化財染織品を視てみると…… (Cultural Textiles under the Scientific View Point) （佐々木(旧姓八木)良子 (Sasaki (née Yagi), Yoshiko), 2008） ・P-42 ・analytical ・ checked against the source by AI
analytical ・ 
checked against the source by AIAlizarin differs from Purpurincontextual
States that alizarin gives scarlet (a clear, yellowish red) on alum mordant, while purpurin gives crimson (a deep red tinged with purple).
Source: 科学の眼で文化財染織品を視てみると…… (Cultural Textiles under the Scientific View Point) （佐々木(旧姓八木)良子 (Sasaki (née Yagi), Yoshiko), 2008） ・P-42 ・institutional summary ・ checked against the source by AI
institutional summary ・ Alizarin ・attributed toThis review article attributes the synthesis of alizarin, the colourant of Western madder, to K. Graebe in 1867.contextual
States that the modern chemical industry was established as a dye industry through, among other things, K. Graebe's synthesis of alizarin (the colourant of Western madder) in 1867.
Source: 天然染料と染色 : 古代の紫を中心に(化学への招待) (Natural dyes and dyeing: with a focus on ancient purple) （吉岡常雄, 上野民夫 (Yoshioka Tsuneo, Ueno Tamio), 1985） ・p.488 要旨 ・textbook ・ checked against the source by AI
textbook ・ Alizarin ・attributed toThis source states that the structure of alizarin (described as 1,2-dihydroxyanthraquinone, the major component of madder) was worked out and replicated in 1868, and that commercial production began in 1869 (citing Travis 1993).contextual
States that the structure of alizarin (1,2-dihydroxyanthraquinone, madder's major component) was replicated in 1868, making it the first natural molecule re-created in a laboratory, with commercial production beginning in 1869 (Travis 1993).
Source: Authenticating Turkey red textiles through material investigations by FTIR and UHPLC （Julie H. Wertz, Anita Quye, David France, Pik Leung Tang, Lesley Richmond, 2017） ・p.2 Discussion of Turkey red ・textbook ・ checked against the source by AI
States that in 1868 Graebe and Liebermann discovered how to prepare alizarin synthetically.
Source: Red, Redder, Madder: Analysis and isolation of anthraquinones from madder roots (Rubia tinctorum) （Goverdina C. H. Derksen (promotoren: J. E. de Groot, A. Capelle; co-promotor: T. A. van Beek), 2001） ・Chapter 1 §1.2.1 p.6 ・textbook ・ checked against the source by AI
Alizarin ・attributed toThis museum record states that alizarine had been discovered decades before Perkin's patent, with a succession of experiments conducted by other chemists, and that Perkin filed a patent to make alizarin commercially accessible in 1869, the exact same month that Graebe, Caro, and Liebermann filed a patent for the same process. The museum states it holds five experimental specimens of mordanted cloth dyed with synthetic alizarine around 1869, mounted on card, showing different patterns and shades, some with notes on the exact formulas used.contextual
States alizarine had been discovered decades before Perkin's patent, with prior experiments by other chemists; Perkin filed a patent to make it commercially accessible in 1869, the same month Graebe, Caro and Liebermann filed for the same process. States the museum holds five of Perkin's experimental mordanted-cloth specimens (c.1869, mounted on card, varied patterns/shades, some with formula notes).
Source: Five early specimen mordanted cloth dyed with alizarin by William Henry Perkin (収蔵品記録 Object Number 1947-118) （Science Museum Group (institutional record; maker credited: A. F. Perkin)） ・収蔵品記録本文 (Object Number 1947-118) ・institutional summary ・ checked against the source by AI
Ruberythric acid contains Alizarincontextual
States ruberythric acid was first isolated in crystalline form by Rochleder in 1851, consists of the aglycone alizarin and a disaccharide, with the sugar later identified as the disaccharide primeverose (xylose + glucose).
Source: Red, Redder, Madder: Analysis and isolation of anthraquinones from madder roots (Rubia tinctorum) （Goverdina C. H. Derksen (promotoren: J. E. de Groot, A. Capelle; co-promotor: T. A. van Beek), 2001） ・Chapter 1 §1.4 p.16 ・textbook ・ checked against the source by AI
Alizarin ・attributed toAlizarin is stated to have first been isolated from Rubia tinctorum by Colin and Robiquet in 1826.contextual
States alizarin was first isolated from Rubia tinctorum by Colin and Robiquet in 1826.
Source: Red, Redder, Madder: Analysis and isolation of anthraquinones from madder roots (Rubia tinctorum) （Goverdina C. H. Derksen (promotoren: J. E. de Groot, A. Capelle; co-promotor: T. A. van Beek), 2001） ・Chapter 1 §1.4 p.16 ・textbook ・ checked against the source by AI
Alizarin bonds via Chelation of anthraquinone colourants with metal ionscontextual
States the structural requirements for a good mordant dye, gives alizarin's 1- and 2-position hydroxyl pKa as 12.0 and 8.2, describes calcium bonding to the 2-OH and aluminium bridging the 1-OH/carbonyl, both at a 2:1 dye:metal ratio; notes Kiel's proposed structure was confirmed 35 years later as a binuclear complex by Soubayrol et al. using solid-state 27Al NMR.
Source: Red, Redder, Madder: Analysis and isolation of anthraquinones from madder roots (Rubia tinctorum) （Goverdina C. H. Derksen (promotoren: J. E. de Groot, A. Capelle; co-promotor: T. A. van Beek), 2001） ・Chapter 1 §1.5.1-1.5.2 p.17-19 ・textbook ・ checked against the source by AI
Alizarin ・attributed toThis source states that the two samples with the highest madder content (both stylistically attributed to the first half of the 19th century) are also among the oldest pieces analysed, and that this result may point towards a progressive replacement of madder by cochineal over the course of the century, though more data are needed to confirm this.contextual
Scope: A hypothesis proposed by the authors themselves based on the analysis of the 26 ikat samples.
Context: The two highest-madder samples are also among the oldest attributed pieces, possibly pointing to madder being progressively replaced by cochineal over the century, though the authors say more data are needed to confirm this.
Source: Exploring the transition from natural to synthetic dyes in the production of 19th-century Central Asian ikat textiles （Diego Tamburini, Eric Breitung, Chika Mori, Tomoko Kotajima, Matthew L. Clarke, Blythe McCarthy, 2020） ・Discussion 中盤（"It was particularly interesting to notice..."の段落） ・analytical ・ checked against the source by AI
Alizarin ・found inIn one orange-coloured area (sample 3) of a 6th-century Coptic wool tapestry (Museum of the Faculty of Arts, Alexandria University, reg. no. 1375), alizarin was detected together with purpurin and treated as the marker for madder dye, interpreted as madder used alone (no woad/indigo detected in this sample).contextual
Scope: This one sample (No.3) from this single Coptic tapestry only; other samples from the same textile contain woad/indigo or other dyes mixed in.
HPLC-DAD detected alizarin (248, 279, 429 nm) and purpurin (256, 293, 480 nm) in sample 3, judged as madder dye alone.
Source: Identification of natural dyes in rare Coptic textile using HPLC-DAD and mass spectroscopy in museum of Faculty of Arts, Alexandria University, Egypt （Harby E. Ahmed; Ibrahim F. Tahoun; Ibrahim Elkholy; Adel B. Shehata; Yassin Ziddan, 2017） ・p.488 §4.1.3 Sample No. 3、p.490 Table 2 ・analytical ・ checked against the source by AI
Alizarin is found in Indigo (indigotin)contextual
Scope: 3 of the 7 samples analysed from this one Coptic tapestry.
Absorption maxima of alizarin/purpurin and of indigotin were detected simultaneously in samples 1, 5 and 6, described as 'a mixture of madder and woad dye'.
Source: Identification of natural dyes in rare Coptic textile using HPLC-DAD and mass spectroscopy in museum of Faculty of Arts, Alexandria University, Egypt （Harby E. Ahmed; Ibrahim F. Tahoun; Ibrahim Elkholy; Adel B. Shehata; Yassin Ziddan, 2017） ・p.488-490 §4.1.1・§4.1.5・§4.1.6、Table 2 ・analytical ・ checked against the source by AI
Lawsone is found in Alizarincontextual
Scope: This one sample (No.2) from this single Coptic tapestry only.
The unassigned peak (251, 288, 440, 487 nm) in sample 2 was analysed by LC-MS-MS and identified as the lawsone compound of henna dye, described as 'a mixture of madder and Henna dye'.
Source: Identification of natural dyes in rare Coptic textile using HPLC-DAD and mass spectroscopy in museum of Faculty of Arts, Alexandria University, Egypt （Harby E. Ahmed; Ibrahim F. Tahoun; Ibrahim Elkholy; Adel B. Shehata; Yassin Ziddan, 2017） ・p.488-489 §4.1.2 Sample No. 2、p.489-490 §4.2、Fig.5 ・analytical ・ checked against the source by AI
Fustic (yellow dye; plant species unspecified across sources) is found in Alizarincontextual
Scope: This one sample (No.7) from this single Coptic tapestry only.
The unassigned peak (242, 274, 307, 340, 487 nm) in sample 7 was analysed by LC-MS-MS and identified as the fisetin (spelled "Fistin" throughout the paper's own text and Fig. 5 legend, likely a typo for the standard "Fisetin") and morin compounds of fustic dye, described as 'a mixture of madder, woad and fustic dye'.
Source: Identification of natural dyes in rare Coptic textile using HPLC-DAD and mass spectroscopy in museum of Faculty of Arts, Alexandria University, Egypt （Harby E. Ahmed; Ibrahim F. Tahoun; Ibrahim Elkholy; Adel B. Shehata; Yassin Ziddan, 2017） ・p.489-490 §4.1.7 Sample No. 7、§4.2 ・analytical ・ checked against the source by AI
Alizarin ・propertyIn the same study, madder-dyed samples were of intermediate lightfastness; microscopy showed the dye present as lake-pigment-like agglomerates adhering to the fibre surface.contextual
Scope: The 4 of the 12 samples judged to be dyed with madder.
Madder-dyed samples showed variable preservation ('relatively well-preserved in some cases and only partially preserved in other cases'), with coloured agglomerates observed adhering to the fibres.
Source: Compositional and Micro-Morphological Characterisation of Red Colourants in Archaeological Textiles from Pharaonic Egypt （Diego Tamburini; Joanne Dyer; Patrizia Davit; Maurizio Aceto; Valentina Turina; Matilde Borla; Marie Vandenbeusch; Monica Gulmini, 2019） ・§2.2.1 Optical Microscopy; §3 Discussion ・analytical ・ checked against the source by AI
Alizarin is found in Flax (linen fibre)contextual
Scope: The 4 of 12 Pharaonic-period (New Kingdom to Late Period) flax-yarn samples identified as madder-dyed (ME2, BM2, BM4, BM5).
All four samples showed alizarin, purpurin, xanthopurpurin, munjistin, pseudopurpurin, anthragallol and two further purpurin isomers; rubiadin was found in two samples (ME2, BM4), ruberythric acid in BM4 only.
Source: Compositional and Micro-Morphological Characterisation of Red Colourants in Archaeological Textiles from Pharaonic Egypt （Diego Tamburini; Joanne Dyer; Patrizia Davit; Maurizio Aceto; Valentina Turina; Matilde Borla; Marie Vandenbeusch; Monica Gulmini, 2019） ・§2.1.2 HPLC-ESI-Q-ToF、Fig.3 ・analytical ・ checked against the source by AI
Alizarin ・mechanismMicroscopic observation in this study suggests that the madder colouration may have resulted from a process resembling lake-pigment formation—with the mordant, dye and fibre combined in the same dye bath—rather than from a direct chemical bond between dye and pre-mordanted fibre surface.contextual
Scope: A hypothesis based on microscopic observation of the madder-dyed samples.
States the coloured agglomerates observed appear to indicate a process similar to lake-pigment formation deposited onto the fibres, and that mixing the mordant, fibres and dye together in the same bath is a possible method used.
Source: Compositional and Micro-Morphological Characterisation of Red Colourants in Archaeological Textiles from Pharaonic Egypt （Diego Tamburini; Joanne Dyer; Patrizia Davit; Maurizio Aceto; Valentina Turina; Matilde Borla; Marie Vandenbeusch; Monica Gulmini, 2019） ・§3 Discussion 第4段落 ・analytical ・ checked against the source by AI
Alizarin is found in Flax (linen fibre)contextual
Scope: The red area of this one linen fragment from Tutankhamun's tomb.
States FORS showed only a wide absorption band between 400-700 nm in the red area, not attributable to known red-dye spectral features, whereas SERS on the gel extract gave peaks (around 1330, 1400, 1448, 1590 cm-1) matching the madder mock-up reference spectrum well.
Source: Applying Gel-Supported Liquid Extraction to Tutankhamun's Textiles for the Identification of Ancient Colorants: A Case Study （Greta Peruzzi; Alessandro Ciccola; Adele Bosi; Ilaria Serafini; Martina Negozio; Nagmeldeen Morshed Hamza; Claudia Moricca; Laura Sadori; Gabriele Favero; Valentina Nigro; Paolo Postorino; Roberta Curini, 2023） ・§2.2.2 FORS; §2.2.3 SERS ・analytical ・ checked against the source by AI
Alizarin ・propertyThis source speculates that madder used with alum and/or tannin may have been preferred over red ochre because it was more colourfast to repeated washing, while also noting that mineral pigments like ochre have advantages such as being usable cold, needing no mordant, and causing (comparatively) slower fibre decay in linen than in wool.contextual
Scope: Includes the author's own speculation.
Speculates madder-plus-mordant may have won out over ochre for better wash-fastness, while crediting mineral pigments with needing no mordant and working cold, and noting mineral-caused fibre decay is slower in linen than in wool.
Source: Red cloth to protect the living and dead （Carolyn Graves-Brown (Egypt Centre, Swansea University), 2022） ・本文後半、"Madder used with alum and/or tannin may have been preferred"の段落 ・practitioner's record ・ checked against the source by AI
practitioner's record ・ Alizarin ・found inThe GI application's dye-plant table (§9.3.2) names Oldenlandia umbellata Linn. ('Indian Madar') as the source of red (alizarin), while the same document's section on dye baths and pastes (§9.3.4) instead names 'maddar (Rubia tinctoria, Rubia manjista)' as the source of the alizarin dye bath — an internal inconsistency in the botanical name.contextual
Scope: Comparison of two sections within Bagru's own GI application
The table's 'Red (Alizarin)' row lists 'Oldenlandia umbellata Linn., local name Indian Madar'.
Source: BAGRU HAND BLOCK PRINT — Application for Registration of a Geographical Indication (Form GI-1) （Bagru Haath Thappa Chhapai Dastkar Sanrakshan Awam Vikas Samiti (BHTCDSAVS)） ・9.3.2節 Dyesの一覧表 ・institutional summary ・ checked against the source by AI
Contradicts: The same document's section on dye baths and pastes (§9.3.4) instead names the alizarin bath's source plants as 'maddar (Rubia tinctoria, Rubia manjista)'.
Source: BAGRU HAND BLOCK PRINT — Application for Registration of a Geographical Indication (Form GI-1) （Bagru Haath Thappa Chhapai Dastkar Sanrakshan Awam Vikas Samiti (BHTCDSAVS)） ・9.3.4節 Alizarine Bath ・institutional summary ・ checked against the source by AI
Alizarin ・propertyBoth GI applications state that synthetic alizarin is used as a substitute because natural alizarin has become less available.contextual
Scope: Glossary sections of both the Bagru and Sanganeri GI applications
States: 'Nowadays synthetic alizarine is used due to shortage of vegetable alizarine.'
Source: BAGRU HAND BLOCK PRINT — Application for Registration of a Geographical Indication (Form GI-1) （Bagru Haath Thappa Chhapai Dastkar Sanrakshan Awam Vikas Samiti (BHTCDSAVS)） ・9.3.4節 Alizarine Bath ・institutional summary ・ checked against the source by AI
States synthetic alizarin is used today due to easy availability and cost.
Source: Syahi Begar hand block printing in India （EcoFab (ブログ著者。氏名の表示なし), 2018） ・Introductionの段落 ・practitioner's record ・ checked against the source by AI
States: nowadays synthetic alizarine is used due to shortage of vegetable alizarine (wording near-identical to Bagru).
Source: SANGANERI HAND BLOCK PRINTING — Application for Registration of a Geographical Indication (Form GI-1) （Calico Printers Co-operative Society Ltd. (CPCSL)） ・9.3.4節 Alizarine Bath ・institutional summary ・ checked against the source by AI
Alizarin differs from Purpurincontextual
Scope: An explanation based on quantum-chemical calculations on model molecules, as reported by a prior study cited in this report (the excited-lifetime values themselves are also from that prior study)
Reports that alizarin forms a stable 6-membered-ring intramolecular hydrogen bond (9-carbonyl/1-hydroxyl) showing ESIPT emission in ethanol, while the purpurin-type structure (hydroxyls at 1,4) does not undergo proton transfer and remains excited longer, citing quantum-chemical model values of 120 ps versus 5.4 ns.
Source: 茜染めにおける金属錯体の形成と耐光性について （井内俊文・野口広貴・伊藤彰浩・仙波健（京都市産業技術研究所 材料・素材技術グループ）, 2024） ・p.10-11 §1「緒言」中盤（先行研究7の引用） ・textbook ・ checked against the source by AI
Alizarin bonds via Chelation of anthraquinone colourants with metal ionspreliminary
Scope: Structural analysis of two powdered lake pigments made from alizarin (1,2-dihydroxyanthraquinone) and Al3+ (lake 1 synthesised from the literature; lake 2 a reproduction of an artist's pigment): solid- and liquid-state NMR, FTIR, mass spectrometry and DFT. Not dyed on fibre.
FTIR showed Al3+ bound to oxygens at C1 and C9; solid-state NMR showed octahedral Al3+ in both lakes; lake 2 consists of neutral complexes with a protonated C2 hydroxyl and is insoluble.
Source: What's the Madder? Characterization of Old Fashioned Alizarin/Aluminum Red Pigments Using Liquid and Solid-State NMR （Leonel C. Silva, Vanessa Otero, Maria J. Melo, Eurico J. Cabrita, Luís Mafra, 2023） ・Abstract；4. Conclusions ・analytical ・ checked against the source by AI
Alizarin ・propertyThe colour of alizarin in a DMSO solution containing residual water depends on its ionisation state: blue at about pH 14 where only the dianion exists, violet near pH 9.9 where mono- and dianions mix. Among the Al lakes, lake 1 with a deprotonated C2 hydroxyl (anionic) has a violet hue, while lake 2 with a protonated C2 hydroxyl (neutral) is a brighter red.preliminary
Scope: Alizarin in DMSO with residual water at different pH, and two powdered Al lakes; not dyed on fibre.
At about pH 14 only Aliz2− exists, blue; near pH 9.9 a mono-/dianion mix gives violet. Lake 2, with protonated 2-OH groups, is less soluble and a brighter red; lake 1 has a violet cast and also dissolves poorly in water.
Source: What's the Madder? Characterization of Old Fashioned Alizarin/Aluminum Red Pigments Using Liquid and Solid-State NMR （Leonel C. Silva, Vanessa Otero, Maria J. Melo, Eurico J. Cabrita, Luís Mafra, 2023） ・3.2 FTIR の節（誌面 pp.607-608） ・analytical ・ checked against the source by AI
Open questions (2)
Was the low alizarin in this Coptic-tapestry sample due to the madder species used, or to a particular dyeing technique?
Regarding why almost no alizarin was detected in this Coptic tapestry sample, the author leaves open whether this was due to the type of madder used at the time (e.g. a wild species low in alizarin) or to a dyeing technique that may have existed to extract only the purpurin component while excluding alizarin, flagging it as a topic for future study.
Why does Bagru's GI application give two different botanical sources (Oldenlandia umbellata vs. Rubia) for alizarin within the same document?
The dye-plant table (§9.3.2) and the section on dye baths and pastes (§9.3.4) of the same document give different botanical names for the source of alizarin: the table names Oldenlandia umbellata, while §9.3.4 names maddar (Rubia tinctoria, Rubia manjista) for the alizarin bath. Neither the application nor any other source checked shows which plant is actually used.