2,3-Dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione
[CAS# 81-59-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anthracenes
• Name: 2,3-Dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione
• Molecular Formula: C₁₄H₁₀O₆
• Molecular Weight: 274.23
• CAS Registry Number: 81-59-4
• EC Number: 201-364-5
• SMILES: C1CC(=O)C2=C(C3=C(C=CC(=C3C(=C2C1=O)O)O)O)O

Properties

• Solubility: Insoluble (1.9E^-3 g/L) (25 °C), Calc.^*
• Density: 1.79±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 543.8±50.0 °C (760 Torr), Calc.^*
• Flash point: 296.8±26.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2021 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2,3-Dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione, commonly known as anthraquinone, has a long history dating back to ancient civilizations where it was extracted from plants for its dyeing properties. The chemical structure of anthraquinone was elucidated in the 19th century, marking a significant milestone in organic chemistry. Its synthesis from anthracene and subsequent derivatization led to the discovery of numerous anthraquinone derivatives with diverse chemical and biological properties. Today, anthraquinone is primarily produced synthetically on an industrial scale, with applications spanning various industries.

Anthraquinone and its derivatives are widely used as dyes and pigments in the textile industry. They impart vibrant and long-lasting colors to fabrics, making them indispensable for dyeing natural and synthetic fibers.

Anthraquinone derivatives are employed as bleaching agents in the pulp and paper industry. They facilitate the removal of lignin and other impurities from wood pulp during the bleaching process, resulting in brighter and more durable paper products.

Anthraquinone derivatives exhibit diverse pharmacological activities, including anticancer, antimicrobial, and antioxidant properties. Compounds such as emodin and aloe-emodin are under investigation for their potential therapeutic applications in cancer treatment, infectious diseases, and inflammatory conditions.

Anthraquinone derivatives serve as valuable intermediates in organic synthesis for the preparation of complex molecules and pharmaceutical compounds. Their functional groups undergo various chemical transformations, including oxidation, reduction, and substitution reactions, enabling the synthesis of diverse organic scaffolds.

Anthraquinone derivatives are explored as electrode materials in rechargeable lithium-ion batteries and redox flow batteries. Their reversible redox behavior and high stability make them promising candidates for energy storage applications, contributing to the development of efficient and sustainable battery technologies.

Anthraquinone derivatives are used as photosensitizers in photography and photodynamic therapy. They sensitize photochemical reactions by absorbing light and generating reactive oxygen species, which can be utilized for image development or targeted destruction of cancer cells in photodynamic therapy.

References

2003. Mitoxantrone. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-13-0163