The blue colourant of indigo dyeing (indigotin). It does not dissolve in water: it is reduced to a water-soluble form (leuco-indigo), taken into the cloth, and oxidised in air back to blue.
Claims and evidence (51)
The limitations noted for some sources are recorded in Japanese only — see the Japanese edition.
Indoxyl produces Indigo (indigotin)contextual
Scope: Under aerobic conditions
States that indoxyl is highly unstable and, on contact with air, is immediately oxidised and spontaneously, non-enzymatically polymerises into stable, insoluble indigo.
Indigo (indigotin) is insoluble in watercontextual
Scope: The source states only that indigo is "insoluble", without naming water as the solvent explicitly. The surrounding context (indigo forming as a precipitate) suggests insolubility in water, but this is not stated explicitly.
Describes the polymerisation product of indoxyl as “stable, insoluble indigo”.
Indigo (indigotin) ・found inAt least 31 species across eight plant families have been documented as indigo-yielding.contextual
States that 31 indigo-yielding species—annual and perennial herbs, shrubs, lianas and trees—across eight plant families have been documented, and that the true number is likely higher, as shown by the example of several indigo-yielding Isatis species alone.
Indigo (indigotin) ・propertyWhen cultivated and extracted in Austria, indigotin content varied greatly by species: Indigofera arrecta was highest at 55%, followed by Persicaria tinctoria (44%), Indigofera tinctoria (23%) and Indigofera suffruticosa (10%). Among species cultivated and extracted in China, Strobilanthes cusia was highest at 56%.supported
Scope: Measured with a standardised hot-extraction method (MME, without lime); Austria- and China-grown samples were compared separately
Reports indigotin content measured with a standardised extraction method (MME) for four species grown in Austria (Indigofera arrecta 55%, Persicaria tinctoria 44%, Indigofera tinctoria 23%, Indigofera suffruticosa 10%) and for Strobilanthes cusia grown in China (56%, statistically significantly higher than the other species tested there).
Indigo (indigotin) ・differenceThis source notes that the word “indigo” is used confusingly in at least four senses—(a) the plants used, (b) the extract as a traded product, (c) the valuable dyeing component, and (d) the colour blue itself—and states that in this article, “indigo” is used for the plant extract and “indigotin” for its valuable dyeing component.contextual
Scope: Terminology as defined in this source (Hartl et al. 2024)
Explains that “indigo” carries at least four meanings—(a) the plants, (b) the extract as a traded product, (c) the valuable dyeing component, (d) the colour blue—and that even the scientific literature conflates them; declares that in this article “indigo” denotes the plant extract and “indigotin” its valuable component, and notes that “indigotin” is also confusingly used for the synthetic food colourant E132.
Indigo (indigotin) is insoluble in watercontextual
States that indigo, the colorant of indigo dyeing, is a dye that does not dissolve in water.
States that indigo's disadvantage is that it is insoluble in water.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"The Natural Indigo Dyeing Process" 節 冒頭 ・
States that indigotin is insoluble in water, dilute alkalis and dilute acids, and that this gives it good wash-fastness.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"Physical and Chemical Properties of Indigotin" 節 ・
Explains that indigo is reduced, taken up by cloth or thread, and then on oxidation reverts to indigo, dyeing it blue.
Captions a diagram stating that indigo is transformed into leucoindigo by the action of indigo-reducing bacteria.
Indigo (indigotin) works by reduction to a soluble form and re-oxidationcontextual
States that leuco-indigo, despite its pale yellow appearance, is also called "indigo-white," and that it is quickly oxidised on contact with air, changing to greenish-blue and finally blue.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"The Natural Indigo Dyeing Process" 節 ・
Describes that once slaked lime is dissolved in and the liquid is stirred, the indoxyl in the water loses hydrogen and oxidises, gradually producing blue indigo.
The fermentation log notes that stirring raises a green foam, which re-oxidises and turns blue.
States reduction temporarily turns the dye from vivid blue to a very pale greenish-yellow colour, and that the dye starts to oxidise back to blue immediately on exposure to air.
Indigo (indigotin) bonds via Mechanical entrapment without covalent bondingcontextual
States that indigo precipitates on the surface of cotton fibres but does not chemically bond with the cellulose; it adheres by weak hydrogen bonding, meaning it can be removed by abrasion or repeated washing.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"The Natural Indigo Dyeing Process" 節、末尾の段落 ・
Indigo (indigotin) has the property of Ring dyeing (white core)contextual
States that when cotton fibres are dyed with indigo, only the outermost fibrils absorb the dye while the core stays white, with the dyed fibrils acting as a barrier that prevents the indigo penetrating further into the undyed part — a phenomenon called "ring dyeing."
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"Ring Dyeing and Substantivity" 節 ・
Indigo (indigotin) ・requiresBuilding up a deep indigo colour is said to require repeated "dip and oxidise" cycles; the more times the cloth is dipped, the deeper the colour, though the gain becomes smaller each time. One study found the increase in depth slowing markedly after the eighth dip, with the colour cast shifting from greenish dark blue toward a redder, less blue tone as dips increased, and judged around ten dips to be optimal.contextual
Scope: Indigo dyeing of cotton, as cited in the source
States that because increased colour depth cannot be achieved by dye concentration alone, the number of dips is increased instead, but that after the eighth dip the gain in depth of shade slows markedly, and that as the number of dips increases there is a shift in colour cast from greenish dark blue to a redder, less blue tone; the optimum number of dips is judged to be about ten.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"Ring Dyeing and Substantivity" 節、末尾 ・
vat dye contains Indigo (indigotin)contextual
States that the colorant of indigo dye is indigo.
Context: States that the main colorant of indigo is indigotin, whose structure was reported by Adolf von Baeyer in 1883.
Source:
Indigo (David Richardson; Sue Richardson, 2016) ・"Indigotin" 節 ・
Indigo (indigotin) ・propertyLists example supplementary wordings for indigo-dyed products: colour may transfer to other items through sweat or rubbing during wear; the colour will whiten with repeated washing; and the item should be washed separately because it bleeds colour when washedcontextual
Scope: Example wording for indigo-dyed products, per BOKEN's list
Lists the three example attention sentences specifically for indigo-dyed items, about sweat/rub transfer, whitening with washing, and the need to wash separately.
Indigo (indigotin) ・propertyProvided the piece is washed thoroughly after dyeing, states vat-dyed indigo has wash fastness of grade 4-5, light fastness (UV carbon-arc) of grade 3-4, and dry rubbing fastness from grade 3 up to grade 5 depending on the item — markedly better than typical plant dyeing generallycontextual
Scope: Figures conditional on thorough post-dye washing, per this source's general account
Conditional on thorough post-dye washing, rates this dyeing type's fastness as very good, citing figures of wash 4-5, light (carbon-arc) 3-4, and dry rubbing 3-5, and stressing the gap versus ordinary plant dyeing.
Indigo (indigotin) has the property of Ring dyeing (white core)contextual
Scope: Vat (fermentation-set etc.) indigo dyeing, per this source's general account
Names wet rubbing as the weak point, giving figures of roughly grade 2 for deep shades and 3-4 for pale ones, then contrasts how shade depth cuts both ways: darker is worse for rubbing but better for light fastness.
Indigo (indigotin) produces Isatincontextual
Scope: The text says it is pale indigo shades that take on a yellowish tinge in sunlight; it does not discuss yellowing of deep shades
States that indigo on the cloth is oxidised by singlet oxygen, generated under UV light, into isatin; after the example that a drop of nitric acid turns it into yellow isatin by the same oxidation, says pale indigo shades likewise take on a yellowish tinge in sunlight, and that the influence of isatin is large as a reason why indigo-dyed cloth yellows. Also says extremely pale shades (kame-nozoki) can turn greenish with ageing, including the effect of sunlight, as the remaining indigo and the yellow isatin mix.
Isatin differs from Indigo (indigotin)contextual
States isatin is water-soluble, so washing basically removes the yellow tinge.
Indigo (indigotin) ・attributed toStates that industrial research on indigo began with Baeyer's 1865 work at the Gewerbeinstitut, which found indole to be the parent substance of indigo, though at that point no source of indole other than the indigo plant itself could be found.contextual
Scope: Concerns the early industrial-research phase on indigo (Baeyer's work).
States that industrial indigo research started with Baeyer's 1865 Gewerbeinstitut work, which identified indole as indigo's parent substance — though at the time no source of indole besides the indigo plant itself was known.
Indigo (indigotin) ・attributed toStates that BASF industrial chemist Heinrich Caro forged a collaboration with Baeyer, who managed to synthesise indigo using different pathways in 1878 and 1880; this success led to a tripartite research-and-development agreement between Baeyer, BASF and Hoechst.contextual
Scope: Concerns the c.1878-1880 collaboration among Baeyer, BASF and Hoechst.
States that the BASF industrial chemist Heinrich Caro forged a collaboration with Baeyer; benefiting from this partnership, Baeyer managed to synthesise indigo using different pathways in 1878 and 1880, igniting industrial interest and leading to a tripartite R&D agreement between Baeyer, BASF and Hoechst.
Indigo (indigotin) ・attributed toStates that BASF took Baeyer's second (toluene-based) route to industrial scale, bringing out an 1880 intermediate that, once reduced, would fix indigo onto printed fabric — but that it failed to attract printers, partly because it was priced at twice that of natural indigo.contextual
Scope: Concerns an 1880 intermediate product that itself was a commercial failure; not yet full-scale supply of synthetic indigo dye itself.
States that BASF industrialised Baeyer's second (toluene-based) route, putting an intermediate on the market by 1880 that could, once reduced, fix indigo onto printed fabric — but that the product failed to win over printers, partly because it was priced at twice the level of natural indigo.
Indigo (indigotin) ・attributed toStates that in 1890 Heumann (Zurich) established a synthesis pathway starting from naphthalene, derived from coal tar; BASF and Hoechst secured rights to use it, and after seven more years of industrial development, synthetic indigo reached the market in 1897 (BASF in July). The name is spelled "Carl Heumann" in one source and "Karl Heumann" in another.contextual
Scope: Concerns the path from establishing the industrial synthesis route to BASF's and Hoechst's market launch.
States that Carl Heumann of Zurich Polytechnic worked out a naphthalene-from-coal-tar route in 1890; BASF and Hoechst quickly bought rights to it, and seven more years of industrial development led to BASF's synthetic-indigo launch in July 1897, with Hoechst close behind.
States that a fresh contribution from Karl Heumann (as spelled in this source), a Zurich professor, in 1890 let BASF beat every competitor to market with "Indigo pure BASF" in 1897.
Indigo (indigotin) ・propertyStates that between 1880 and 1896 the average annual value of world output of plant-derived indigo was estimated at 80 million marks, equal to the combined turnover of all European coal-tar dye factories (citing Reinhardt and Travis).contextual
States, citing Reinhardt and Travis (2000), that plant-derived indigo's average annual world output value from 1880-1896 — 80 million marks — matched the combined revenue of every European coal-tar dye factory.
Indigo (indigotin) ・causesStates that cheaper, purer German synthetic indigo, launched in 1897, rapidly ate into demand for natural indigo—first in Germany, then in British, French and American markets—and that total exports from Calcutta (which mainly shipped Bihar indigo) "plummeted"; per Table 2, export weight from Calcutta fell from 111,714 cwt in 1895-6 to 19,062 cwt in 1905-6, to less than a fifth of the 1895-6 total within a decade.contextual
States that after synthetic indigo's 1897 appearance, natural-indigo demand was rapidly eaten into first in the German then the British, French and American markets, and that total exports from Calcutta plummeted; Table 2 shows a fall from 111,714 cwt (1895-6) to 19,062 cwt (1905-6), to under a fifth of the 1895-6 total within a decade.
Indigo (indigotin) ・differenceStates that most Western cotton printers quickly switched to synthetic indigo for its purity, and natural indigo never won back this market segment; but niche demand persisted (e.g. woollen dyeing, for technical reasons), and some dyers mixed a small amount of natural (Bengal) indigo into synthetic indigo to improve fastness or obtain a distinctive coppery-red tinge.contextual
States that most Western cotton printers quickly switched to synthetic indigo, showing a strong preference for its purity, and that natural indigo never won back this segment of "purity-conscious" consumers; it notes niche demand such as woollen dyeing (for technical reasons) and dyers who mixed a little Bengal indigo with synthetic indigo to improve fastness or obtain a coppery-red tinge.
Indigofera suffruticosa produces Indigo (indigotin)supported
Scope: A comparative cultivation study in Sakon Nakhon Province (May-Sep 2023, RCBD, 4 plots per treatment). Note: for the light-condition comparison, the source's own discussion text right after Table 3 contains a sentence stating the opposite (that I. tinctoria was higher), while the abstract, conclusion and Table 3's own numbers all agree that I. suffruticosa was higher (apparently an internal inconsistency in the source itself).
Tables 1-3 show Indigofera suffruticosa's YIBL (indigo blue yield per fresh leaf weight) higher than I. tinctoria across pod stage, harvest time and light conditions, with ANOVA showing p < 0.05 significance.
Indigo (indigotin) ・requiresIndigo-dyed threads tended to show elevated calcium; the authors suggest this may reflect use of a calcium source (such as burnt shell) to alkalise the indigo vat.preliminary
Scope: The indigo-dyed threads among those mapped by XRF that showed elevated calcium.
Calcium turned up in every thread, reaching its peak in two black cotton threads coloured with an indigo dye (from Indigofera or Cybistax) combined with a yellow, and its lowest levels in most red threads and undyed cotton. The authors propose calcium may likewise have served as a dyeing auxiliary, and that its being elevated in strongly indigoid threads could point to a calcium source, such as burnt shell, used to alkalise the vat.
Indigo (indigotin) ・found inThis blog post (Andean Textile Arts) states that the oldest surviving example of indigo-dyed cloth is Peruvian in origin and reportedly more than 6,000 years old.contextual
Context: In previewing upcoming colour topics, the post mentions indigo, asking readers whether they know that the oldest surviving sample of indigo-dyed cloth is said to be Peruvian and dates back more than 6,000 years.
6,6'-Dibromoindigo (Tyrian purple) differs from Indigo (indigotin)contextual
Refers to the structure as 6,6'-dibromoindigo and states Friedländer identified it in 1909, distinguishing it from unbrominated indigo by that bromine substitution.
Explains that the pigment's substance is an organic compound called dibromoindigo, which contains bromine among its constituent elements.
Indigo (indigotin) ・used inThis record states that in Cambodian silk ikat indigo was used for blue, alongside bror hut bark for yellow, lac for red and mok clua for blackcontextual
Scope: A 1996 record; the same paragraph adds that most dyeing today uses chemical dyes
Lists indigo for blue and mok clua (ebony fruit) for black among the colours used, adding that most dyeing today is chemical.
Indigo (indigotin) ・found inIndigo is said to have also been used to dye the ivory fittings of a small knife, 'Ryokuge Bachiru no Tsuka Saya Onto-su', once owned by Emperor Shomu, revealing that plant dyes were used broadly even on crafts other than textiles.preliminary
Scope: The ivory fittings of a small knife owned by Emperor Shomu
States indigo was also used to dye the ivory fittings of a knife owned by Emperor Shomu, showing plant dyes were used broadly beyond textiles.
Indigo (indigotin) ・found inAll the blue-colored areas analyzed (the bodies of the sutra wrapper for Shōjō-zakkyō and sutra wrapper No.1, the body and hem of sutra wrapper No.3, among others) are said to have shown a reflectance spectrum characteristic of indigo (ai), showing that indigo had been used.preliminary
Scope: All blue-colored areas of the Shosoin sutra wrappers analyzed
States all analyzed blue-colored areas showed a reflectance spectrum characteristic of indigo.
Indigo (indigotin) ・used inThe green-colored areas, such as the body of sutra wrapper No.3 (g4, g5), are said to have shown indigo by visible spectroscopy and Amur cork tree by fluorescence spectroscopy, showing that the green was produced by over-dyeing indigo with Amur cork tree.preliminary
Scope: The green-colored areas of the Shosoin sutra wrappers analyzed
States the green areas (g4, g5) of the body of sutra wrapper No.3 showed an indigo-characteristic visible spectrum and Amur-cork-tree fluorescence peaks, indicating over-dyeing of indigo with Amur cork tree.
Indigo (indigotin) ・propertyThis dye workshop states that even properly-dyed indigo products retain some dye that the fibre could not absorb, so colour initially transfers onto clothing or skin (though it washes off with soap); repeated washing and drying settles the colour, but settling is said to take many years.contextual
Scope: Regarding Mizuno Dye Works' indigo products (traditional vat-dyed)
States that even with the honzome technique properly applied there is a limit to how much dye the fibre can absorb, and the excess unabsorbed dye rubs off; repeating washing and drying settles the colour but this takes many years, so at first it may transfer to clothes or skin, though it comes off easily with soap.
Indigo (indigotin) ・propertyThis dye workshop states there is no way to stop indigo colour loss outright, but thoroughly washing out the dye that failed to fix helps the colour settle and stabilise; it also states that storing an item in the dark for one to two years causes the indigo to 'harden' and stop rubbing off, without explaining what this hardening means chemically.contextual
Scope: Regarding Mizuno Dye Works' indigo products
States colour loss cannot be stopped, but thoroughly removing what can be removed helps the colour settle and stabilise, and that shade-drying/storing in the dark for one to two years causes the indigo to harden and stop rubbing off.
Indigo (indigotin) ・mechanismAs a remedy when indigo colour has transferred onto another item, this dye workshop gives the procedure: soak the affected item in lukewarm water with a mild-alkaline detergent and bleach added for 30 minutes to an hour, rinse once the colour has lifted, then do a normal wash.contextual
Instructs putting a mild-alkaline detergent plus bleach into lukewarm water, soaking for 30 minutes to an hour, rinsing once the colour has lifted, then doing a normal wash.
Indigo (indigotin) ・requiresFor home laundering of indigo products, this dye workshop gives the procedure: put a neutral detergent in lukewarm water, press-wash it, rinse by press-washing again in lukewarm water, optionally use fabric softener, and shade-dry in a well-ventilated spot; it also advises not washing it with other items, not rubbing hard, storing away from light, and ironing from the reverse side.contextual
Gives the steps: put neutral detergent in lukewarm water, press-wash, rinse by press-washing in lukewarm water again, optionally use fabric softener, and shade-dry somewhere well-ventilated; lists as cautions not washing with other items, press-washing gently rather than rubbing hard, storing away from light, and ironing from the reverse side.
Indigo (indigotin) ・mechanismContinuing, Berthollet states that this alkaline solution of indigo decomposes on contact with the atmosphere, and the indigo recombines with the oxygen it draws from the air, returning to its natural (blue) state. He explains that when a fabric is dyed in an indigo vat it takes on a green colour, but turns blue as soon as it is exposed to air, because the indigo recombines with oxygen drawn from the atmosphere, while the alkali or lime is carried off by washing.contextual
Scope: The theory of the indigo vat, on the change from green to blue.
Explains that fabric dyed in an indigo vat turns green, but becomes blue on air exposure because 'l'indigo se recombine avec l'oxygène qu'il attire de l'atmosphère' (the indigo recombines with the oxygen it draws from the atmosphere).
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'.
Indigo (indigotin) ・found inIn sample 4 (a blue-toned area) of the same Coptic tapestry, only indigotin and indirubin were detected, with no alizarin or purpurin (madder) found.contextual
Scope: This one sample (No.4) from this single Coptic tapestry only.
Sample 4 showed only indigotin (RT 31.49 min, 242/285/330/610 nm) and indirubin (RT 33.23 min, 239/290/363/542 nm), classified as woad dye alone.
Indigo (indigotin) is attributed to Woadcontextual
Scope: The paper's own general background statement, not specific to Egypt.
Context: States Indigofera tinctoria had, by the mid-17th century, almost completely replaced European woad, and both lost importance after synthetic indigo's introduction in 1882.
Indigo (indigotin) is found in Flax (linen fibre)contextual
Scope: The blue area of this one linen fragment from Tutankhamun's tomb.
SERS spectra of the gel extract from the blue area showed characteristic peaks of indigotin (1073, 1176, 1369, 1470 cm-1) and indirubin (645, 971, 1404, 1585 cm-1), with the latter more intense, probably due to thermal degradation of the dye.
Indigo (indigotin) ・propertyPer the article, India and El Salvador are described as the two biggest producers of natural indigo; the market also has cheap chemical indigo and natural indigo "impure"/adulterated with synthetic dyes. The article quotes Ahmad as saying many dyers use adulterated dye while calling it natural indigo, knowingly or not.contextual
States India and El Salvador are the two biggest natural-indigo producers and that cheap chemical indigo and synthetic-adulterated "impure" indigo also circulate, followed by Ahmad's quoted remark that many dyers use adulterated dye under the "natural indigo" name, knowingly or not.
Source:
Local indigo goes global (Sohel Parvez, 2018) ・記事後半(『India and El Salvador are the two biggest producers...』の段落と直後の引用) ・
Indigo (indigotin) ・why it fell out of useThis article states natural indigo first displaced woad almost completely by the end of the 17th century, driven by growing indigo production in India paired with industrialisation-driven demand in Europe, but the synthesis of indigo by German chemist Adolf von Baeyer and the start of commercial production in 1897 then caused both woad and global natural-indigo cultivation to collapse.contextual
States indigo nearly displaced woad by the end of the 17th century, and that Baeyer's synthesis plus commercial production from 1897 collapsed both woad and natural indigo cultivation.
Indigo (indigotin) causes Ring dyeing (white core)contextual
States indigo is unique among major textile dyes for its very low affinity for cotton fibre, so the ball-warp dyeing process ring-dyes the cotton; with almost any other dye this outcome would be considered a defect.
sulfur dye differs from Indigo (indigotin)contextual
Scope: Comparison of ozone-treated pure-indigo and indigo/sulfur-mixed denim
States the three fabrics dyed with indigo/sulfur mixtures (Fabrics 6-8) responded less to ozone than the five indigo-only fabrics, and speculates this is because sulfur dyes' sulfur-linkage-based chemical structure is less susceptible than indigo's carbon-carbon double bond to ozone cleavage.
Indigo (indigotin) produces Isatincontextual
States ozone cleavage of indigo's chemical structure yields isatin, citing the treated water's UV-Vis spectrum following that of a reference isatin sample as evidence.
Kubovaya naboyka (Russian indigo vat-dye resist block printing) requires Indigo (indigotin)contextual
States indigo was imported via Arkhangelsk from the mid-17th century, with Moscow offering the best prices by 1900 (remote areas could be over double).
Indigo (indigotin) produces Isatincontextual
Scope: Yellowing of indigo-dyed fabric (denim etc.) during storage
States the symptom was an indigo-dyed shirt yellowing during storage; states that indigo-dyed fabric can yellow in some cases because of three factors: residue from the decomposition of bleach agent (sodium hypochlorite), oxidative decomposition by UV light, and the action of atmospheric nitrogen oxides (NOx). Says these influences decompose the indigo dye to form isatin, which causes the yellowing.
Isatin differs from Indigo (indigotin)contextual
As a supplementary note, states isatin is water-soluble and removable by washing, but because it forms from decomposition of the indigo dye, the washed colour ends up paler than the original.
Indigo (indigotin) is applicable to Chemical reduction of indigo (chemical vat)contextual
Scope: Maiwa's general explanation of indigo vats
Breaks every indigo vat down into just three ingredients — the pigment, something to reduce it, and something alkaline — and lists sugars, certain natural dyestuffs or plant matter, and chemicals as the options for that middle, reducing role.
Source:
Indigo — Natural Dyes (Maiwa) ・"HOW TO DYE WITH INDIGO"、"All indigo vats need three things"の一文と"A reducing agent"の項 ・
Indigotine / Indigo Carmine (Food Blue No. 2) differs from Indigo (indigotin)contextual
States it is made by sulfonating indigo, implying it is a water-soluble derivative distinct from insoluble indigo itself.
Source:
食用色素の化学 (片山脩, 1974) ・誌面623頁「V. インジゴイド系食用色素」の項 ・