Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H8O4 |
| Molecular Weight | 240.2109 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O
InChI
InChIKey=RGCKGOZRHPZPFP-UHFFFAOYSA-N
InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
| Molecular Formula | C14H8O4 |
| Molecular Weight | 240.2109 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created using several sources including:
https://www.ncbi.nlm.nih.gov/pubmed/4179464; http://www.fda.gov/downloads/scienceresearch/specialtopics/regulatoryscience/ucm484318.pdf; http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfpcd/classification.cfm?id=317; https://clinicaltrials.gov/ct2/show/NCT02329548?term=ALIZARIN&rank=1
Curator's Comment: Description was created using several sources including:
https://www.ncbi.nlm.nih.gov/pubmed/4179464; http://www.fda.gov/downloads/scienceresearch/specialtopics/regulatoryscience/ucm484318.pdf; http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfpcd/classification.cfm?id=317; https://clinicaltrials.gov/ct2/show/NCT02329548?term=ALIZARIN&rank=1
Alizarin is an anthraquinone is an organic compound that has been used as a red dye, principally for dyeing textile fabrics since ancient times. Historically it was derived from the roots of the madder plant Rubia tinctorum, in which it occurs combined with the sugars xylose and glucose. Laboratory methods of preparing alizarin from anthraquinone were discovered in 1868, and, upon commercial introduction of the synthetic dye in 1871, the natural product disappeared from the market for textile dyes. At present alizarin is commonly used in biomedical studies involving bone growth, osteoporosis, bone marrow, calcium deposits in the vascular system, cellular signaling, gene expression, tissue engineering, and mesenchymal stem cells. Alizarin precipitates free calcium, and tissue block containing calcium stain red immediately when immersed in alizarin. It is approved by FDA as a Calcium test system for clinical chemistry. Alizarin red, has been used for a quantitative sweat measure to characterize the sweat distribution in patients with syncope, anxiety, and POTS.
Originator
Curator's Comment: The alizarin component became the first natural dye to be synthetically duplicated in 1868 when the German chemists Carl Graebe and Carl Liebermann, working for BASF, found a way to produce it from anthracene. he English dye chemist William Henry Perkin independently discovered the same synthesis, although the BASF group filed their patent before Perkin by only one day.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2364030 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Alizarin Sulfonate, Calcium Approved UseA calcium test system is a device intended to measure the total calcium level in serum. Calcium measurements are used in the diagnosis and treatment of parathyroid disease, a variety of bone diseases, chronic renal disease and tetany (intermittent muscular contractions or spasms). |
|||
| Diagnostic | Alizarin Sulfonate, Calcium Approved UseA calcium test system is a device intended to measure the total calcium level in serum. Calcium measurements are used in the diagnosis and treatment of parathyroid disease, a variety of bone diseases, chronic renal disease and tetany (intermittent muscular contractions or spasms). |
|||
| Diagnostic | Alizarin Sulfonate, Calcium Approved UseA calcium test system is a device intended to measure the total calcium level in serum. Calcium measurements are used in the diagnosis and treatment of parathyroid disease, a variety of bone diseases, chronic renal disease and tetany (intermittent muscular contractions or spasms). |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Low sensitivity of retina to AMPA-induced calcification. | 2003-05-15 |
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| Increased endothelial cell density in the paracentral and peripheral regions of the human cornea. | 2003-05 |
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| Glucuronidation activity of the UGT2B17 enzyme toward xenobiotics. | 2003-05 |
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| Calcification of modern foldable hydrogel intraocular lens designs. | 2003-04 |
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| Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection. | 2003-03-14 |
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| Effects of autologous serum on osteoblastic differentiation in human bone marrow cells. | 2003-03 |
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| Viscoanesthesia. Part I: toxicity to corneal endothelial cells in a rabbit model. | 2003-03 |
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| S100A4: a novel negative regulator of mineralization and osteoblast differentiation. | 2003-03 |
|
| Milwaukee shoulder: correlating possible etiologic variables. | 2003-02 |
|
| The human umbilical cord blood: a potential source for osteoblast progenitor cells. | 2003-02 |
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| Black tea extract and dental caries formation in hamsters. | 2003-01 |
|
| Effect of hypothyroidism and thyroxin replacement on growth of long bones in prenatally treated albino rats. | 2003-01 |
|
| Postnatal development of the fore- and hindlimbs in the grey short-tailed opossum, Monodelphis domestica. | 2003-01 |
|
| Synovial fluid features and their relations to osteoarthritis severity: new findings from sequential studies. | 2003-01 |
|
| A new rapid radiological procedure for routine teratological use in bone ossification assessment: a supplement for staining methods. | 2002-12 |
|
| RGD peptides immobilized on a mechanically deformable surface promote osteoblast differentiation. | 2002-12 |
|
| Osteogenic potential of rabbit marrow stromal stem cells cultured in vitro: a histochemical and scanning electron microscopic study. | 2002-12 |
|
| Spectrophotometric determination of phenylephrine HCl and orphenadrine citrate in pure and in dosage forms. | 2002-11-07 |
|
| Triiodide ion and alizarin red S as two new reagents for the determination of clotrimazole and ketoconazole. | 2002-11-07 |
|
| Hydrophilic acrylic intraocular lens optic and haptics opacification in a diabetic patient: bilateral case report and clinicopathologic correlation. | 2002-11 |
|
| Enhancement of osteogenesis on hydroxyapatite surface coated with synthetic peptide (EEEEEEEPRGDT) in vitro. | 2002-11 |
|
| Evaluation of the developmental toxicity of annatto in the rat. | 2002-11 |
|
| Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. | 2002-10-31 |
|
| Effects of intraocular epinephrine on the corneal endothelium of rabbits. | 2002-10 |
|
| Simultaneous determination of zirconium and molybdenum by first-derivative spectrophotometry. | 2002-10 |
|
| Facile colorimetric methods for the quantitative determination of tetramisole hydrochloride. | 2002-10 |
|
| Bone remodelling and tumour grade modifications induced by interactions between bone and swarm rat chondrosarcoma. | 2002-10 |
|
| Establishment of a novel chondrocytic cell line N1511 derived from p53-null mice. | 2002-10 |
|
| Strong static magnetic field stimulates bone formation to a definite orientation in vitro and in vivo. | 2002-10 |
|
| The amino bisphosphonate ibandronate prevents calciphylaxis in the rat at doses that inhibit bone resorption. | 2002-10 |
|
| Synthesis of functionally graded MgCO3 apatite accelerating osteoblast adhesion. | 2002-10 |
|
| Establishment and characterization of a new osteogenic cell line (MOS-J) from a spontaneous C57BL/6J mouse osteosarcoma. | 2002-09-13 |
|
| The effects of sevelamer hydrochloride and calcium carbonate on kidney calcification in uremic rats. | 2002-09 |
|
| Cartilage intermediate layer protein expression in calcium pyrophosphate dihydrate crystal deposition disease. | 2002-08 |
|
| Calcinosis cutis in chronic renal failure diagnosed by fine needle aspiration. A case report. | 2002-07-31 |
|
| Spectrophotometric determination of piroxicam and tenoxicam in pharmaceutical formulations using alizarin. | 2002-07-20 |
|
| Late postoperative complication of the foldable lens implantation: opacification of the intraocular lenses. | 2002-07 |
|
| [Morphogenesis of media calcinosis in Mönckeberg disease. Light microscopy, scanning electron microscopy and roentgen microanalysis findings]. | 2002-07 |
|
| A histomorphometric study of adaptive responses of cancellous bone in different regions in the sheep mandibular condyle following experimental forward mandibular displacement. | 2002-07 |
|
| Peroxidase-mediated transformation of hydroxy-9,10-anthraquinones. | 2002-07 |
|
| Caffeine, quercetin and alizarin stimulate the exhalation of metabolic products of [14C]-N-nitrosodiethylamine in mice. | 2002-06 |
|
| [Osteogenic potential of fibroblasts with reconstituted telomerase activity]. | 2002-05 |
|
| Effect of prenatal doxycycline administration on skeletal differentiation in long bones of Albino rat. | 2002-05 |
|
| Vitrification of posterior corneal lamellae. | 2002-04 |
|
| Establishment of a rat long-term culture expressing the osteogenic phenotype: dependence on dexamethasone and FGF-2. | 2002 |
|
| Bone formation in the context of growth retardation induced by hIGFBP-1 overexpression in transgenic mice. | 2002 |
|
| Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration. | 2002 |
|
| The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations--a cautionary tale. | 2001-10-07 |
|
| Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates. | 2001-09-07 |
|
| [The effects of leptin on proliferation and function of human osteoblast]. | 2001-06 |
Sample Use Guides
Osteogenic differentiation of caprine bone marrow-derived mononuclear cells was studied using alizarin red staining of mononuclear cells seeded on on oxidized graphene in presence of fetal bovine serum-containing regular growth
medium and osteocyte differentiation medium after 21 days in culture. Alizarin red content detected in in the osteocytes was about 10-220 uM.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:29:14 GMT 2025
by
admin
on
Mon Mar 31 18:29:14 GMT 2025
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| Record UNII |
60MEW57T9G
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C461
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m1513
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87358
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6293
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ALIZARIN
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60MEW57T9G
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C80142
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C010078
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16866
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200-782-5
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72-48-0
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7212
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DTXSID5045960
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PARENT -> CONSTITUENT ALWAYS PRESENT |
