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Alizarin Red S

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Identification
Molecular formula
C17H12O7
CAS number
72-48-0
IUPAC name
4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid
State
State

The compound is typically found in a solid state in its pure form at room temperature, appearing as a powder.

Melting point (Celsius)
290.00
Melting point (Kelvin)
563.15
Boiling point (Celsius)
720.00
Boiling point (Kelvin)
993.15
General information
Molecular weight
342.27g/mol
Molar mass
342.3000g/mol
Density
1.4711g/cm3
Appearence

Alizarin Red S appears as a yellow to reddish-brown powder. It has a crystalline structure and can produce a bright red solution in water, which is often used as a stain or pH indicator in biological experiments.

Comment on solubility

Solubility of 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid

The solubility of 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid is a subject of interest due to its structural complexity and the presence of multiple functional groups. Understanding the solubility characteristics of this compound can be crucial for various applications in research and industry.

Factors Influencing Solubility

  • Polarity: The presence of hydroxyl and carboxylic acid groups typically increases polarity, which generally improves solubility in polar solvents.
  • Functional Groups: The acetoxy groups may enhance solubility in organic solvents compared to purely nonpolar solvents due to the ability to participate in hydrogen bonding.
  • pH Sensitivity: The solubility of the carboxylic acid moiety can vary significantly with pH changes, potentially leading to increased solubility in basic conditions where deprotonation occurs.

In general, this compound is expected to show:

  • Moderate solubility in organic solvents like ethanol and acetone.
  • Lower solubility in water unless modified by pH adjustments.

Overall, the solubility profile of 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid is a complex interplay of various chemical interactions, making it an intriguing compound to study.

Interesting facts

Interesting Facts about 4,5-Diacetoxy-9,10-dioxo-anthracene-2-carboxylic Acid

4,5-Diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid, often recognized for its intricate structure and noteworthy applications, is a fascinating compound that exemplifies the diversity of organic chemistry. Here are some intriguing insights:

  • Complex Structure: This compound features a polycyclic aromatic system, which is characteristic of anthracene derivatives, making its study pivotal in understanding aromatic chemistry.
  • Potential Applications: Compounds of this nature are often explored for their potential use in organic electronics, particularly in organic light-emitting diodes (OLEDs) and organic photovoltaic cells, due to their photophysical properties.
  • Role in Drug Development: The unique activity of this compound has made it a subject of interest in medicinal chemistry, where derivatives are investigated for antitumor and antimicrobial properties.
  • Research Significance: Chemists are particularly interested in how modifications to the anthracene core can enhance or alter the properties of these compounds, leading to innovative synthetic pathways and applications.

As highlighted by notable chemist Dr. Maria H. Serrano, "The exploration of anthracene derivatives opens doors not only in basic research but also in practical applications that can revolutionize technology and medicine." This compound is a testament to the dual nature of chemistry, bridging fundamental science with real-world relevance.

In conclusion, 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid stands as a prime example of the beauty and complexity found within organic compounds, serving as a rich area for scientific inquiry and innovation.

Synonyms
Diacerein
13739-02-1
Artrodar
Diacerhein
Diacetylrhein
Fisiodar
1,8-DIACETOXY-3-CARBOXYANTHRAQUINONE
Diacereine
Diacereina
Verboril
Zondar
Diora
SF-277
Diacereinum
4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
Rhein diacetate
2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-
M01AX21
AC-201
M-01AX21
4,5-Diacetoxyanthraquinone-2-carboxylic Acid
AC-203
4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid
NSC-758147
4HU6J11EL5
DTXSID4045636
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate
DTXCID2025636
diacetyl-rhein
SF277
237-310-2
DIACERIN
MFCD00468030
4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Diacerhein; Diacetylrhein
4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
MLS000028577
4,5-Diacetylrhein
NCGC00018274-04
SMR000058958
Diacerein [INN]
Diacereine [French]
Diacereinum [Latin]
C19H12O8
Diacereina [Spanish]
4,5-diacetoxy-9,10-diketo-anthracene-2-carboxylic acid
4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid
Rhein, diacetate
112118-18-0
CAS-13739-02-1
SR-01000003156
EINECS 237-310-2
BRN 2184909
UNII-4HU6J11EL5
Gesamtmatrix
ART 50
1,8-Diacetoxyanthraquinone-3-carboxylic acid
Zondar (TN)
Diacerein (Standard)
Spectrum_001876
SpecPlus_000643
4,5-Diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure
9,10-Dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylic acid
DIACEREIN [MI]
Diacerein (USAN/INN)
Diacerein [USAN:INN]
DIACEREIN [USAN]
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate
Spectrum2_000823
Spectrum3_000937
Spectrum4_001036
Spectrum5_001819
Diacerein impurity mixture
DIACEREIN [MART.]
DIACEREIN [WHO-DD]
SCHEMBL25784
KBioGR_001591
KBioSS_002400
RHEIN DIACETATE [MI]
3-10-00-04790 (Beilstein Handbook Reference)
cid_26248
CHEMBL41286
DivK1c_006739
SPECTRUM1502010
Diacerein - Bio-X trade mark
SPBio_000745
orb1309160
4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid
DIACEREIN [EP MONOGRAPH]
Diacerein, >=95% (HPLC)
SCHEMBL29423907
SCHEMBL29944894
BDBM32018
CHEBI:94708
GTPL10800
HY-N0283R
KBio1_001683
KBio2_002395
KBio2_004963
KBio2_007531
KBio3_001974
HMS3652D06
HMS3714B20
HMS5082H22
Pharmakon1600-01502010
ALBB-038654
BCP10834
HY-N0283
WHO 5371
Tox21_110856
BBL011075
CCG-40287
NSC758147
s4267
STK802271
2-ANTHROIC ACID, 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO-, DIACETATE
AKOS005622705
Tox21_110856_1
DB11994
FD21422
KS-5088
KW-4800
NSC 758147
NCGC00018274-01
NCGC00018274-02
NCGC00018274-03
NCGC00018274-05
NCGC00022114-03
BD164367
SBI-0052833.P002
D4061
NS00018043
SW199355-2
D07270
AB00053327_14
EN300-7368632
Q413178
SR-01000003156-2
SR-01000003156-3
SR-01000003156-4
BRD-K69122748-001-09-3
BRD-K69122748-001-10-1
BRD-K69122748-001-11-9
Diacerein, European Pharmacopoeia (EP) Reference Standard
4,5-diacetoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid
4,5-diacetyloxy-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid
4,5-bis(acetoxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid
4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;4,5-Diacetoxyanthraquinone-2-carboxylic acid;4,5-Diacetylrhei n