A3882

Alizarin-3-methyliminodiacetic acid

Name: Alizarin-3-methyliminodiacetic acid
Brand: SIGMA

≥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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All Photos(2)

About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₅NO₈

CAS Number:

3952-78-1

Molecular Weight:

385.32

NACRES:

NA.32

PubChem Substance ID:

24890823

UNSPSC Code:

12352204

EC Number:

223-544-2

MDL number:

MFCD00001202

Beilstein/REAXYS Number:

2190028

Product Name

Alizarin-3-methyliminodiacetic acid,

SMILES string

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

InChI key

PWIGYBONXWGOQE-UHFFFAOYSA-N

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)

assay

≥98% (TLC)

form

powder

solubility

1 M NaOH: 10 mg/mL, blue to purple

Quality Level

100

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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

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.

Legal Information

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Bis(2-pyridylmethyl)amine-functionalized alizarin: an efficient and simple colorimetric sensor for fluoride and a fluorescence turn-on sensor for Al3+ in an organic solution.

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

Swimming behaviour and calcium incorporation into inner ear otoliths of fish after vestibular nerve transection.

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

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)

Revisiting in vivo staining with alizarin red S--a valuable approach to analyse zebrafish skeletal mineralization during development and regeneration.

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;

Allogeneic bone grafting of calvarial defects: an experimental study in the rabbit.

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

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