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Alizarin

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Identification
Molecular formula
C14H8O4
CAS number
72-48-0
IUPAC name
1,2-dihydroxyanthracene-9,10-dione
State
State

Alizarin is a solid at room temperature. It is commonly found in a crystalline form due to its use as a dye, ensuring ease of handling and uniformity in dyeing processes.

Melting point (Celsius)
277.00
Melting point (Kelvin)
550.15
Boiling point (Celsius)
633.00
Boiling point (Kelvin)
906.15
General information
Molecular weight
240.21g/mol
Molar mass
240.2110g/mol
Density
1.5080g/cm3
Appearence

Alizarin typically appears as an orange-red solid or crystal. It can vary slightly in shade depending on its formulation, but its vibrant color is a key characteristic, especially notable because it has been historically used as a dye.

Comment on solubility

Solubility of 1,2-Dihydroxyanthracene-9,10-dione (C14H8O4)

1,2-Dihydroxyanthracene-9,10-dione, also known as chrysazin, presents interesting solubility characteristics relevant for various applications in organic chemistry and materials science. Here’s a comprehensive look at its solubility:

  • Solvent Compatibility: This compound is primarily soluble in organic solvents.
  • Polar Solvents: It shows limited solubility in polar solvents such as water due to the hydrophobic nature of the anthracene ring.
  • Non-Polar Solvents: It is much more soluble in non-polar or weakly polar solvents like ethyl acetate or benzene.
  • Temperature Dependence: The solubility can significantly increase with temperature, enabling better applications in varying experimental conditions.

As a general rule, the presence of hydroxyl groups can enhance the solubility in certain solvents, yet the overall structure maintains a preference for organic environments. Understanding these solubility properties is vital for optimizing its use in various chemical processes and formulations.


Interesting facts

Interesting Facts about 1,2-Dihydroxyanthracene-9,10-dione

1,2-Dihydroxyanthracene-9,10-dione, also known as quinizarin, is a fascinating organic compound with a rich history and a variety of applications. Here are some intriguing aspects of this compound:

  • Structural Significance: The compound features a fused ring structure characteristic of anthraquinone derivatives, making it a valuable building block in various synthetic applications.
  • Colorful Applications: Quinizarin is renowned for its vibrant color, which has led to its use as a dye in textiles, plastics, and even in some artistic applications. It is especially prized for its fastness to light.
  • Roles in Research: In the realm of scientific research, 1,2-dihydroxyanthracene-9,10-dione has been studied for its potential in organic electronic devices due to its semiconducting properties.
  • Biological Impact: Studies have indicated that compounds like quinizarin may exhibit biological activity, potentially influencing various metabolic pathways and presenting avenues for pharmaceutical development.
  • Historical Context: The synthesis of quinizarin has been a topic of interest since the 19th century, showcasing the evolution of organic chemistry practices.

This compound is not just a pigment; it represents a unique intersection of chemistry, art, and technology. As we continue to explore its properties and applications, 1,2-dihydroxyanthracene-9,10-dione stands as a testament to the importance of interdisciplinary research in advancing our understanding of chemical compounds.

Synonyms
Alizarin
72-48-0
Alizarin Red
1,2-dihydroxyanthracene-9,10-dione
Mordant Red 11
1,2-Dihydroxyanthraquinone
1,2-Dihydroxy-9,10-anthracenedione
Alizarin B
Turkey Red
ALIZARINE
1,2-Anthraquinonediol
Alizarina
Alizarine Red
Eljon Madder
Alizarine B
Alizarine NAC
Alizarine Red B
Alizarine Red L
Alizerine NAC
Eljon Madder M
1,2-Dihydroxy-9,10-anthraquinone
Alizarine 3B
Alizarine L paste
Alizarine Red IP
Turkey Red W
Alizarine indicator
Alizarine Red B2
Certiqual Alizarine
Alizarine Red IPP
Alizerine Red IPP
Mitsui Alizarine B
Sanyo Carmine L2B
Mitsui Alizarine BS
Certiqual Alizarine D
Alizarine Lake Red 2P
Alizarine Lake Red 3P
Alizarine Lake Red IPX
C.I. Mordant Red 11
1,2-Dihydroxyanthra-9,10-quinone
C.I. Mordant Red 11C
1,2-Dihydroxy anthraquinone
D And C Orange Number 15
D and C Orange Number 15D
Deep Crimson Madder 10821
Deep Crimson Madder 10821E
1,2-Dihydroxyanthrachinon
C.I. 58000
Alizarine paste 20% bluish
9,10-Anthracenedione, 1,2-dihydroxy-
Alizarine Paste 20 percent Bluish
C.I. 58000C
1,2-Dihydroxy-anthraquinone
D and C Orange No. 15
Anthraquinonic
CCRIS 3530
Anthraquinone, 1,2-dihydroxy-
CHEBI:16866
NSC7212
CI 58000
NSC 7212
EINECS 200-782-5
UNII-60MEW57T9G
MFCD00001201
BRN 1914037
60MEW57T9G
1322-60-7
DTXSID5045960
AI3-18244
NSC-7212
1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
DIHYDROXY-9,10-ANTHRACENEDIONE
CHEMBL55814
DTXCID3025960
ROUGE COVALAC W 3514
4-08-00-03256 (Beilstein Handbook Reference)
Az
D&C ORANGE NO. 15 (DELISTED)
NCGC00095227-01
Turkey Red (VAN)
CAS-72-48-0
1,2-Dihydroxyanthrachinon [Czech]
Hystazarin
Pincoffin
Alizarin (C.I. 58000)
Alizarin, p.a.
Alizarin (Standard)
Sanyo Carmine l2BT
ATHRAQUINONES A
Spectrum_000386
SpecPlus_000320
9, 1,2-dihydroxy-
ALIZARIN [MI]
Spectrum2_000397
Spectrum3_000262
Spectrum4_001555
Spectrum5_000150
Epitope ID:116187
SCHEMBL18614
BSPBio_001704
CBDivE_014227
KBioGR_002050
KBioSS_000866
SPECTRUM210850
MLS002207283
DivK1c_006416
Alizarin, Dye content 97 %
SPBio_000613
HY-N0563R
KBio1_001360
KBio2_000866
KBio2_003434
KBio2_006002
KBio3_001204
HMS1923C03
HMS3651P05
1,10-dihydroxy-2,9-anthraquinone
2,9-dihydroxy-1,10-anthraquinone
9,10-dihydroxy-1,2-anthraquinone
HY-N0563
Tox21_111486
BBL027327
BDBM50206434
CCG-38668
MSK160876
s2526
STK801841
AKOS001639988
Tox21_111486_1
1,2-Dihydroxyanthra-9,10-quinone #
9,10-Anthraquinone, 1,2-dihydroxy-
FA39740
FS-3935
LN: L C666 BV IVJ EQ FQ1
SDCCGMLS-0066502.P001
NCGC00095227-02
NCGC00095227-03
NCGC00095227-04
NCGC00095227-06
1,2-bis(oxidanyl)anthracene-9,10-dione
AC-11708
DA-50329
NCI60_041501
SMR001306798
SY012985
1,2-Dihydroxyanthraquinone;Mordant Red 11
CS-0009103
D0242
NS00013520
SW101224-2
C01474
EN300-136088
F17721
A837539
AE-641/00185064
Q267813
SR-05000002485
SR-05000002485-1
BRD-K73191876-001-04-7
BRD-K73191876-001-11-2
BRD-K73191876-001-12-0
F0905-1727
200-782-5
InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18