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Revision as of 11:22, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chem← Previous edit Latest revision as of 23:28, 10 August 2024 edit undo2601:18d:881:fba0:e9bc:119d:5fac:8274 (talk)No edit summaryTag: Visual edit 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443852980
| Watchedfields = changed
⚫ |ImageFile=Haematein.png
⚫ | verifiedrevid = 443854327
⚫ |ImageSize=
⚫ | ImageFile=Haematein.png
⚫ |IUPACName=3,4,6a,10-Tetrahydroxy-6,7-dihydroindenochromen-9-one
⚫ | ImageSize=200px
|OtherNames=
⚫ | IUPACName=3,4,6a,10-Tetrahydroxy-6,7-dihydroindenochromen-9-one
⚫ |Section1= {{Chembox Identifiers
| OtherNames=Haematein; Haematein
⚫ | CASNo=475-25-2
⚫ |Section1={{Chembox Identifiers
⚫ | PubChem=10138
| UNII_Ref = {{fdacite|correct|FDA}} | CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo=475-25-2
⚫ | PubChem=10138
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 88Q1SYD10B | UNII = 88Q1SYD10B
| SMILES=C1C2=CC(=O)C(=CC2=C3C1(COC4=C3C=CC(=C4O)O)O)O | SMILES=C1C2=CC(=O)C(=CC2=C3C1(COC4=C3C=CC(=C4O)O)O)O
| MeSHName=Hematein | MeSHName=Hematein
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ }}
| ChemSpiderID = 9732
⚫ |Section2= {{Chembox Properties
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| Formula=C<sub>16</sub>H<sub>12</sub>O<sub>6</sub>
| ChEMBL = 1360563
| MolarMass=300.26 g/mol
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | Appearance=
| ChEBI = 90116
⚫ | Density=
| InChI = 1/C16H12O6/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/h1-4,17,19-21H,5-6H2
⚫ | MeltingPt=
| InChIKey = HLUCICHZHWJHLL-UHFFFAOYAU
⚫ | BoilingPt=
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | Solubility=
| StdInChI = 1S/C16H12O6/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/h1-4,17,19-21H,5-6H2
⚫ }}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ |Section3= {{Chembox Hazards
| StdInChIKey = HLUCICHZHWJHLL-UHFFFAOYSA-N
⚫ | MainHazards=
⚫ }}
⚫ | FlashPt=
⚫ |Section2={{Chembox Properties
| Autoignition=
| C=16 | H=12 | O=6
⚫ }}
⚫ | Appearance=
⚫ | Density=
⚫ | MeltingPt=
⚫ | BoilingPt=
⚫ | Solubility=
⚫ }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards=
⚫ | FlashPt=
| AutoignitionPt =
⚫ }}
}} }}


'''Hematein''' (US spelling) or '''haematein''' is an oxidized derivative of ], used in staining. Haematein must not be confused with ], which is a brown to black iron-containing pigment formed by decomposition of ]. In the Colour Index (but nowhere else), haematein is called haematine, a confusing word that wrongly implies that the compound is an amine. '''Hematein''' (US spelling) or '''haematein''' is an oxidized derivative of ], used in staining. Haematein should not be confused with ], which is a brown to black iron-containing pigment formed by decomposition of ]. In the Colour Index (but nowhere else), haematein is called haematine.


==Properties==
Hematein exhibits indicator-like properties, being blue and less soluble in aqueous alkaline conditions, and red and more soluble in alcoholic acidic conditions. In acidic conditions, complexes of hematein with metals (usually aluminium or ferric iron) bind to arginine residues of nuclear histones. The color of the stained nuclei depends on the salt used. Aluminium-haematein complexes are usually blue, whereas ferric complexes are very dark blue or black.
Hematein exhibits indicator-like properties, being blue and less soluble in aqueous ] conditions, and red and more soluble in alcoholic ] conditions. Dissolved haematein slowly reacts with atmospheric ], yielding products that have not found applications.


==Applications==
⚫ Structures that stain with aluminium-hematein (haemalum) are often said to be basophilic, but the staining mechanism is not as simple as for basic (cationic) dyes with smaller molecules. Truly basophilic structures are ones containing nucleic acids or other polyanions such as glycosaminoglycans of extracellular matrix or acidic glycoproteins in many types of mucus. As usually used, aluminium-hematein stains only nuclear chromatin and a few other materials such as keratohyalin granules and calcified deposits. Very dilute solutions of aluminium-haematein, used at pH3.2 (higher than is usual for staining), contain a cationic dye-metal complex and will slowly stain nucleic acids (Bettinger & Zimmermann 1991). Haemalum solutions used for routine staining are more concentrated and more acidic (pH2-2.5) and are able to stain nuclei after chemical or enzymatic extraction of DNA and RNA from the tissue (Lillie et al., 1976).
In acidic solutions, complexes of hematein with metals (usually ] or ], but also ], ] and several others) are used as biological stains. Aluminium-haematein (haemalum) is the "routine" stain for cell nuclei in sections of human and other animal tissues. Metal-haematein stains are available also for objects other than nuclei, including ]s of nerve fibres and various cytoplasmic ]s. The color of the stained objects depends on the salt used. Aluminium-haematein complexes are usually blue, whereas ferric complexes are very dark blue or black.

Aluminium-haematein complexes (haemalum) bind to the chromatin of the ] of cells. Although haemalum staining methods have been in use since the 1860s, the chemical identity of the substance or substances that bind the dye-metal complex is still not known with certainty. Some histochemical investigations clearly indicate that a cationic aluminium-haematein complex is attracted to the ] anions of ]. Others implicate the ] residues of nuclear ]s as the substrate of nuclear staining by haemalum.<ref>{{Cite journal | author = Puchtler, H., Meloan, S.N., Waldrop, F.S. | year = 1986 | title = Application of current chemical concepts to metal-haematein and -brazilein stains | journal = Histochemistry | volume = 85 | pages = 353–364 | doi = 10.1007/BF00982665 | pmid = 2430916 | issue = 5| s2cid = 7384777 }}</ref>
⚫ Structures that stain with aluminium-hematein (haemalum) are often said to be ], but the staining mechanism is not as simple as for basic (cationic) dyes with smaller molecules. Truly basophilic structures are ones containing ]s or other ] such as glycosaminoglycans of extracellular matrix or acidic ]s in many types of mucus. As usually used, aluminium-hematein stains only nuclear chromatin and a few other materials such as keratohyalin granules and calcified deposits. Very dilute solutions of aluminium-haematein, used at pH 3.2 (higher than is usual for staining), contain a cationic dye-metal complex and will slowly stain nucleic acids.<ref>{{cite journal |author1=Bettinger, C. |author2=Zimmermann, H.W. | year = 1991 | title = New investigations on hematoxylin, hematein, and hematein-aluminium complexes. 2. Hematein-aluminium complexes and hemalum staining | journal = Histochemistry | volume = 96 | pages = 215–228 | doi = 10.1007/BF00271540 | pmid = 1717413 | issue = 3|s2cid=23504301 }}</ref> Haemalum solutions used for routine staining are more concentrated and more acidic (pH 2-2.5) and are able to stain nuclei after chemical or enzymatic extraction of DNA and RNA from the tissue.<ref>{{cite journal | author = Lillie, R.D., Donaldson, P.T. & Pizzolato, P. | year = 1976 | title = The effect of graded 60C nitric acid extraction and of deoxyribonuclease digestion on nuclear staining by metachrome mordant dye metal salt mixtures | journal = Histochemistry | volume = 46 | pages = 297–306 | doi = 10.1007/BF02464419 | pmid = 57109 | issue = 4| s2cid = 13154258 }}</ref>


==References== ==References==
{{No footnotes|date=January 2011}}
* Lillie, R.D., Donaldson, P.T. & Pizzolato, P. (1976). The effect of graded 60C nitric acid extraction and of deoxyribonuclease digestion on nuclear staining by metachrome mordant dye metal salt mixtures. Histochemistry 46: 297-306.
* Bettinger, C. & Zimmermann, H.W. (1991). New investigations on hematoxylin, hematein, and hematein-aluminium complexes. 2. Hematein-aluminium complexes and hemalum staining. Histochemistry 96: 215-228.
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