Acacetin
[CAS# 480-44-4]

Identification

• Classification: Natural product >> Flavonoids
• Name: Acacetin
• Synonyms: 5,7-Dihydroxy-4'-methoxyflavone; 5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• CAS Registry Number: 480-44-4
• EC Number: 207-552-3
• SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Melting point: 260 - 265 °C (Expl.)
• Boiling point: 518.6±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 198.3±23.6 °C (Calc.)^*
• Index of refraction: 1.669 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Acacetin is a natural flavonoid compound classified under the flavone subgroup, commonly found in various plants such as Acacia, Robinia pseudoacacia (black locust), and Turnera diffusa (damiana). It has the molecular formula C₁₆H₁₂O₅ and a characteristic structure featuring a 4'-methoxy group and hydroxyl groups at positions 5 and 7 on the flavone backbone.

Acacetin was first isolated from natural sources during phytochemical investigations of medicinal plants. Its discovery contributed to the broader understanding of flavonoid diversity and their role in plant physiology. Flavonoids, including acacetin, serve multiple biological functions in plants, such as UV filtration, symbiotic nitrogen fixation, and defense against pathogens.

In recent decades, acacetin has attracted considerable attention for its biological activities relevant to human health. Studies have identified it as possessing antioxidant, anti-inflammatory, antimicrobial, and anticancer properties. The antioxidant activity of acacetin is linked to its ability to scavenge reactive oxygen species and chelate metal ions, thus protecting cells from oxidative damage.

Pharmacologically, acacetin has been investigated for its cardioprotective effects. It modulates various molecular pathways related to cardiac function, such as inhibiting phosphodiesterase enzymes and regulating ion channels, which may help in arrhythmia management. Furthermore, acacetin demonstrates potential neuroprotective effects through mechanisms involving reduction of neuroinflammation and protection against neurodegeneration.

In addition to its biological effects, acacetin serves as a valuable chemical scaffold in medicinal chemistry for the development of novel therapeutic agents. Its flavone structure allows for various chemical modifications to enhance bioavailability and target specificity.

Applications of acacetin extend beyond medicine into the food and cosmetic industries, where its antioxidant properties contribute to product stabilization and preservation. Extracts rich in acacetin are also used in traditional herbal remedies, underscoring its ethnopharmacological relevance.

Overall, acacetin represents a significant natural compound with multifaceted biological activities and promising therapeutic potential. Ongoing research continues to elucidate its mechanisms of action and optimize its applications in health sciences.

References

2025. New Acacetin Glycosides from the Genus Dracocephalum. Chemistry of Natural Compounds, 61(3).
DOI: 10.1007/s10600-025-04676-5

2019. Selective Inhibition of Human Monoamine Oxidase B by Acacetin 7-Methyl Ether Isolated from Turnera diffusa (Damiana). Molecules, 24(4).
DOI: 10.3390/molecules24040810

2017. Acacetin protects against cardiac remodeling after myocardial infarction by mediating MAPK and PI3K/Akt signal pathway. Journal of Pharmacological Sciences, 135(4).
DOI: 10.1016/j.jphs.2017.11.009