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Alizarin

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Identification
Molecular formula
C14H8O4
CAS number
72-48-0
IUPAC name
4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
State
State

Alizarin is typically found in a solid state at room temperature, presenting as orange or red crystals or powder.

Melting point (Celsius)
290.00
Melting point (Kelvin)
563.15
Boiling point (Celsius)
522.00
Boiling point (Kelvin)
795.15
General information
Molecular weight
240.21g/mol
Molar mass
240.2070g/mol
Density
1.5110g/cm3
Appearence

Alizarin is a red dye that appears as orange needles when in its solid form. It is typically used in textile dyeing and can also be found as a powder. It exhibits a bright red color which has historical significance in the manufacture of red pigments for art materials.

Comment on solubility

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

The solubility of 4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid (C15H10O5) is influenced by several factors, primarily due to its complex molecular structure. This compound presents intriguing solubility characteristics which can be summarized as follows:

  • Polarity: Due to the presence of multiple hydroxyl (-OH) and carboxylic acid (-COOH) groups, the compound exhibits a significant degree of polarity, enhancing its ability to interact with polar solvents.
  • Solvent Interaction: It is more likely to be soluble in polar solvents such as water and methanol compared to non-polar solvents like hexane.
  • pH Sensitivity: The solubility can change with pH levels. For instance, in stronger acidic conditions, the carboxylic group can become protonated, potentially decreasing solubility.
  • Temperature Dependency: Like many organic compounds, the solubility of this acid can increase with temperature, allowing for better dissolution in solvents when heated.

In conclusion, while 4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid shows promising solubility in polar solvents, its solubility behavior remains dependent on factors such as temperature and pH. Understanding these characteristics is essential for any applications involving this compound.

Interesting facts

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

4,5-Dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid, often referred to as a significant derivative of anthracene, is a fascinating compound in the field of organic chemistry. This molecule holds particular importance due to its unique chemical structure and potential applications. Here are some compelling aspects of this compound:

  • Structural Significance: Its structure includes multiple functional groups, such as hydroxyl and carboxylic acid, which contribute to its chemical reactivity and acidity. The presence of the anthracene backbone adds to its stability and optical properties.
  • Photochemical Properties: The 9,10-dioxo group showcases the compound’s ability to engage in photochemical reactions. These reactions can lead to interesting polymerization processes and the formation of larger systems from smaller units.
  • Potential Applications: 4,5-Dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid has been studied for its use in various fields, including materials science and organic electronics. Its derivatives can serve in the development of organic semiconductors and solar cells.
  • Biological Relevance: Some compounds related to this structure have shown potential in medicinal chemistry, illustrating how structural modifications can yield compounds with enhanced biological activity.

In summary, 4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid exemplifies how a single compound can bridge various scientific domains—from materials science to biochemistry. The versatility and reactivity of this compound not only make it a subject of academic intrigue but also pave the way for practical applications that could lead to innovative technologies.

Synonyms
Rhein
478-43-3
Monorhein
Rhubarb Yellow
Cassic acid
Rheic acid
1,8-Dihydroxy-3-carboxyanthraquinone
4,5-Dihydroxyanthraquinone-2-carboxylic acid
Chrysazin-3-carboxylic acid
1,8-Dihydroxyanthraquinone-3-carboxylic acid
dipropionyl rhein
NSC 38629
Parietic acid
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
CCRIS 5129
2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
EINECS 207-521-4
YM64C2P6UX
BRN 2222155
DTXSID4026000
4,5-Dihydroxy-2-anthraquinonecarboxylic acid
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
NSC-38629
RHEIN [MI]
9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
DTXCID606000
1,8-dihydroxy-3-carboxyl-9,10-anthraquinone
4-10-00-04088 (Beilstein Handbook Reference)
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid
2-Anthraquinonecarboxylic acid, 4,5-dihydroxy-
DIHYDROXY-3-CARBOXYLANTHRAQUINONE, 1,8-
RHEIN [INCI]
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-(8CI)
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
MFCD00009618
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)
MLS000069639
CHEBI:8825
4,5-DiOH-anthraquinone-2-COOH
SMR000058210
Rheinic acid
1,8-DIHYDROXY-3-CARBOXYL ANTHRAQUINONE
C15H8O6
Rhein(Monorhein)
UNII-YM64C2P6UX
Rhein (Standard)
RHN
Rhein; Rhubarb Yellow
Rhein, technical grade
4ie7
ST057726
regid855879
Rhein, analytical standard
SCHEMBL25253
US9238626, Rhein
cid_10168
MLS006011744
CHEMBL418068
MEGxp0_001866
4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
ACon1_000217
BDBM32021
HY-N0105R
GLXC-05271
BCP28202
FDC16642
HY-N0105
MSK40045
NSC38629
Tox21_201098
4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylicacid
BBL009695
LMPK13040015
s2400
STL141046
AKOS005259272
AC-7978
CS-5239
DB13174
FR27724
NCGC00018199-01
NCGC00018199-02
NCGC00018199-03
NCGC00018199-04
NCGC00018199-05
NCGC00018199-06
NCGC00018199-07
NCGC00023342-03
NCGC00023342-04
NCGC00258650-01
AS-11635
CAS-478-43-3
SY051290
DB-014981
D3986
NS00015851
4, 5-Dihydroxyanthraquinone-2-carboxylic acid
EN300-303248
Q720356
4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylicacid
BRD-K27335680-001-01-9
BRD-K27335680-001-10-0
2-Anthroic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
4,5-dihydroxy-9,10-diketo-anthracene-2-carboxylic acid
2-Anthracenecarboxylic acid,10-dihydro-4,5-dihydroxy-9,10-dioxo-
4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid
4,5-bis(oxidanyl)-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid
4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid #
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracene carboxylic acid
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9CI
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic Acid-13C6
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid;4,5-Dihydroxy-2-anthraquinonecarboxylic acid;Chrysazin-3-carboxyli c acid