517-28-2

Basic information

• Product Name: Hematoxylin
• Synonyms: GILL 2 METHOD HEMATOXYLIN STAIN;GILL HEMATOXYLIN SOLUTION NO II;GILL'S HEMATOXYLIN NO 2;GILL'S HEMATOXYLIN SOLUTION NO 2;GILLS II HAEMATOXYLIN;HEMATOXYLIN STAIN, GILL 2;HEMATOXYLIN SOLUTION GILL NO 2;HEMATOXYLIN, GILL II
• CAS NO: 517-28-2
• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28
• EINECS: 208-237-3
• Product Categories: Colours, Dyes, Indicators & Pigments;Cytology StainsHematology and Histology;Hematology and Histology;Routine Histology Stains;marker;Inhibitors;Polymethine;Flavone;Miscellaneous
• Mol File: 517-28-2.mol

Chemical Properties

• Melting Point: 200 °C (dec.)(lit.)
• Boiling Point: 363.32°C (rough estimate)
• Flash Point: 304.5 °C
• Appearance: Yellow to Brown/Powder/Solid
• Density: 1.2514 (rough estimate)
• Vapor Pressure: 2.74E-14mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Soluble in 95% ethanol(1 mg/mL).
• PKA: 6.7(at 25℃)
• Water Solubility: SOLUBLE IN HOT WATER
• Sensitive: Light Sensitive
• Stability: Stability Stable, but may discolour on exposure to light. Incompatible with strong oxidizing agents.
• Merck: 14,4637
• BRN: 91399
• CAS DataBase Reference: Hematoxylin(CAS DataBase Reference)
• NIST Chemistry Reference: Hematoxylin(517-28-2)
• EPA Substance Registry System: Hematoxylin(517-28-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MH7875000
• TSCA: Yes
• Hazardous Substances Data: 517-28-2(Hazardous Substances Data)

Usage

Uses

Used in Ink Industry:
Hematoxylin is used as a colorant in the ink industry, providing a distinctive color to the inks for various purposes.
Used in Histology:
Hematoxylin is used as a biological stain in histology, specifically in the Hematoxylin and eosin (H&E) stain. This stain is one of the most commonly used in the field, allowing for the examination of cell nuclei under a microscope. Hematoxylin forms metal-haematein complexes that stain cell nuclei, aiding in the identification of basophilic structures, even though the staining mechanism differs from that of basic dyes.

Air & Water Reactions

Soluble in hot water, slightly water soluble in cold .

Reactivity Profile

Sensitive to light. .

Hazard

May be carcinogenic.

Purification Methods

Hematoxylin recrystallises from H2O (as trihydrate) in white-yellow crystals which become red on exposure to light and then melt at 100-120o. It has been recrystallised from Me2CO/*C6H6. It has been recrystallised as well from dilute aqueous NaHSO3 until colourless and is soluble in alkali, borax and glycerol. Store it in the dark below 0o. [Morsingh & Robinson Tetrahedron 26 182 1970, Dann & Hofmann Chem Ber 98 1498 1955, Beilstein 17/8 V 469.]

InChI:InChI=1/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16-/m1/s1

Synthetic route

(6aS,11bR)-7,11b-Dihydro-indeno[2,1-c]chromene-3,4,6a,9,10-pentaol; compound with GENERIC INORGANIC NEUTRAL COMPONENT → Hematoxylin (517-28-2)

Conditions	Yield
In hydrogenchloride at 30.1 - 60.1℃; Equilibrium constant;

Hematoxylin (517-28-2) → (6aS,11bR)-7,11b-Dihydro-indeno[2,1-c]chromene-3,4,6a,9,10-pentaol; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions	Yield
With zirconyl chloride In hydrogenchloride at 30.1 - 60.1℃; Thermodynamic data; Equilibrium constant; KA, reaction enthalpy ΔH, standard reaction entropy ΔS0;

Downstream Products

• 474-07-7 (+)-brazilin 
• 1360437-07-5 C₂₆H₂₄O₅ 
• 1360437-06-4 C₂₇H₂₃F₃O₈S 
• 1360437-02-0 C₂₆H₂₄O₆ 
• 1360437-01-9 C₂₆H₂₄O₆ 
• 1360437-17-7 C₂₆H₂₄O₅ 
• 1360437-13-3 C₂₇H₂₃F₃O₈S 

Relevant articles and documents

The Reaction of Hematoxylin with Zirconyl Chloride Studied Spectrophotometrically

The reaction of hematoxylin with zirconyl chloride in acid solutions was studied spectrophotometrically.A strong absorption band with λmax = 525 nm is attributed to a loose complex formed between hemateine and zirconium(IV) ions.The experimental findings - especially the fact that the linear absorption coefficient increases with time, passes through a maximum and then declines exponentially - are consistent with a four step mechanism.Two of the steps are fast equilibria, while the other two are slow dissociation reactions, the second being an order of magnitude faster than the first.The rate constants for the slow steps and the equillibrium constants for the fast steps have been determined.From the variation of these constants with temperature the activation parameters of the slow reactions and thermodynamic data for the fast equilibria have been calculated.Also the molar absorption coefficient of the absorbing complex has been estimated.Possible analytical applications of the reactions studied are briefly discussed. - Keywords: Zirconyl chloride, Hematoxylin complex formation rates, Activation parameters of complexes, Thermodynamic data of complexes