A3882

Alizarin-3-methyliminodiacetic acid

Name: Alizarin-3-methyliminodiacetic acid
Brand: SIGMA
Price: 189 USD

≥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

Key Documents

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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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Show Differences

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This Item	A5533	D6518	195073
Sigma-Aldrich A3882 Alizarin-3-methyliminodiacetic acid	Sigma-Aldrich A5533 Alizarin Red S	Sigma-Aldrich D6518 Diethylenetriaminepentaacetic acid	Sigma-Aldrich 195073 Mordant Orange 1
assay ≥98% (TLC)	assay -	assay ≥99% (titration)	assay -
solubility 1 M NaOH: 10 mg/mL, blue to purple	solubility H₂O: 1 mg/mL	solubility 1 M HCl: 50 mg/mL, clear, colorless	solubility 1 N NH₄OH: 1%, clear
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form powder

General description

Alizarin-3-methyliminodiacetic acid is used in the colorimetric detection of fluorine.[1] It is a dye[2] employed to stain mineralized bones of the preserved specimen from vertebrates.[3]

Application

Alizarin-3-methyliminodiacetic acid has been used:

for live staining of mineralized bone matrix[4]
to double-label the bone for dynamic bone histomorphometry[5] at the femoral mid-diaphysis in the rat[6]
as a label in histomorphometry of the tibial diaphysis to indicate new bone formation in the rat[7]

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

Enhanced efficiency in isolation and expansion of hAMSCs via dual enzyme digestion and micro-carrier.

Bi Foua Claude Alain Gohi et al.

Cell & bioscience, 10, 2-2 (2020-01-11)

A two-stage method of obtaining viable human amniotic stem cells (hAMSCs) in large-scale is described. First, human amniotic stem cells are isolated via dual enzyme (collagenase II and DNAase I) digestion. Next, relying on a culture of the cells from

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

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Alizarin-3-methyliminodiacetic acid