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A3882

Sigma-Aldrich

Alizarin-3-methyliminodiacetic acid

≥98% (TLC), powder

Synonym(s):

N-(carboxymethyl)-N-[(9,10-dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenyl)methyl]-glycine, 3,4-Dihydroxyanthraquinon-2-yl-methylimino-diacetic acid, Alizarin Complexone, Alizarin Fluorine Blue

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About This Item

Empirical Formula (Hill Notation):
C19H15NO8
CAS Number:
Molecular Weight:
385.32
Beilstein:
2190028
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

Alizarin-3-methyliminodiacetic acid,

Assay

≥98% (TLC)

form

powder

solubility

1 M NaOH: 10 mg/mL, blue to purple

SMILES string

OC(=O)CN(CC(O)=O)Cc1cc2C(=O)c3ccccc3C(=O)c2c(O)c1O

InChI

1S/C19H15NO8/c21-13(22)7-20(8-14(23)24)6-9-5-12-15(19(28)16(9)25)18(27)11-4-2-1-3-10(11)17(12)26/h1-5,25,28H,6-8H2,(H,21,22)(H,23,24)

InChI key

PWIGYBONXWGOQE-UHFFFAOYSA-N

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General description

Alizarin-3-methyliminodiacetic acid is used in the colorimetric detection of fluorine. It is a dye employed to stain mineralized bones of the preserved specimen from vertebrates.

Application

Alizarin-3-methyliminodiacetic acid has been used:
  • for live staining of mineralized bone matrix
  • to double-label the bone for dynamic bone histomorphometry at the femoral mid-diaphysis in the rat
  • as a label in histomorphometry of the tibial diaphysis to indicate new bone formation in the rat

Legal Information

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An evaluation of staining techniques for marking daily growth in scleractinian corals
Holcomb M, et al.
Journal of Experimental Marine Biology and Ecology, 440, 126-131 (2013)
A Bensimon-Brito et al.
BMC developmental biology, 16, 2-2 (2016-01-21)
The correct evaluation of mineralization is fundamental for the study of skeletal development, maintenance, and regeneration. Current methods to visualize mineralized tissue in zebrafish rely on: 1) fixed specimens; 2) radiographic and μCT techniques, that are ultimately limited in resolution;
Fábio de S Dias et al.
Talanta, 89, 276-279 (2012-01-31)
In the present study, a minicolumn of sisal fiber loaded with alizarin fluorine blue is proposed as a preconcentration system for copper determination in tobacco leaf samples by flame atomic absorption spectrometry. During the optimization procedure, a two level full
Ling Zhu et al.
Dalton transactions (Cambridge, England : 2003), 48(15), 5035-5047 (2019-03-28)
A complexone analog chemosensor, H2L, bearing chelating bis(2-pyridylmethyl) amine and alizarin groups was synthesized via the Mannich reaction. H2L chromically responds to OH-, F-, CH3COO-, and H2PO4- in DMF, CH3CN, and acetone, but not in CH3OH or H2O. The addition
R H Anken et al.
Advances in space research : the official journal of the Committee on Space Research (COSPAR), 30(4), 721-725 (2003-01-17)
Inner ear stones (otoliths) of larval cichlid fish Oreochromis mossambicus were marked with the calcium-tracer alizarin-complexone (AC) at 1 g earth gravity before and after a 3, 7, 14 or 21 days stay of the animals at hypergravity conditions (hg;

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