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Merck
CN

A3882

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:
3952-78-1
Molecular Weight:
385.32
Beilstein:
2190028
EC Number:
223-544-2
MDL number:
MFCD00001202
UNSPSC Code:
12352204
PubChem Substance ID:
24890823
NACRES:
NA.32

Key Documents

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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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6306V
WXBF4570V
WXBF1926V
MKCS7233
WXBD9654V

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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;
J M Shand et al.
International journal of oral and maxillofacial surgery, 31(5), 525-531 (2002-11-07)
The purpose of this study was to investigate the incorporation of fresh frozen irradiated membranous allogeneic bone grafts into critical size calvarial defects in the rabbit. Fifteen rabbits had calvarial defects prepared. Twelve rabbits received allogeneic grafts and three received
E Edelmann et al.
Advances in space research : the official journal of the Committee on Space Research (COSPAR), 33(8), 1390-1394 (2005-04-05)
Previous investigations on neonate swordtail fish (Xiphophorus helleri) revealed that otolithic calcium incorporation (visualized using the calcium tracer alizarin complexone) and thus otolith growth had ceased after nerve transection, supporting a hypothesis according to which the gravity-dependent otolith growth is
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
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