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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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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

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Product Name

Alizarin-3-methyliminodiacetic acid,

assay

≥98% (TLC)

Quality Level

100

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

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

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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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;

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

Influence of hypergravity on fish inner ear otoliths: I. Developmental growth profile.

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;

A study of the regional distribution of bone formed around hydroxyapatite implants in the tibiae of streptozotocin-induced diabetic rats using multiple fluorescent labeling and confocal laser scanning microscopy.

S Iyama et al.

Journal of periodontology, 68(12), 1169-1175 (1998-01-28)

The present study was designed to compare the amount and regional distribution of bone formation around hydroxyapatite (HA) implants in normal (control) rats with that of animals with diabetes mellitus (DM), induced by streptozotocin 2 weeks prior to implant placement.

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Global Trade Item Number

SKU	GTIN
A3882-10G	04061833368176
A3882-1G	04061833368183
A3882-5G	04061838820495

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