4-(4-Hydroxyphenyl)-2-butanone
[CAS# 5471-51-2]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: 4-(4-Hydroxyphenyl)-2-butanone
• Synonyms: 1-(4-Hydroxyphenyl)-3-butanone; 4-(4-Hydroxyphenyl)butan-2-one; Raspberry keton; Frambinone
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20
• CAS Registry Number: 5471-51-2
• EC Number: 226-806-4
• FEMA: 2588
• SMILES: CC(=O)CCC1=CC=C(C=C1)O

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 81 - 85 °C (Expl.)
• Boiling point: 292.2±15.0 °C 760 mmHg (Calc.)^*
• Flash point: 122.9±13.0 °C (Calc.)^*
• Index of refraction: 1.535 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4-(4-Hydroxyphenyl)-2-butanone is an organic compound consisting of a butanone backbone substituted at the 4-position with a 4-hydroxyphenyl group. Its molecular formula is C₁₀H₁₂O₂, reflecting the presence of a ketone functional group, an aromatic ring bearing a hydroxyl group, and an aliphatic carbon chain.

The compound belongs to the class of aryl ketones, combining the characteristics of both aromatic and carbonyl functional groups. The 4-hydroxyphenyl substituent introduces phenolic properties, including acidity and the potential for hydrogen bonding through the hydroxyl group. This group also affects the compound’s electronic distribution, influencing its reactivity and interactions.

Chemically, the ketone group at the 2-position of the butanone chain is reactive towards nucleophiles and can undergo typical carbonyl chemistry, such as nucleophilic addition, oxidation, and reduction reactions. The proximity of the aromatic ring to the ketone moiety can influence these reactions through conjugation and steric effects.

Synthesis of 4-(4-hydroxyphenyl)-2-butanone typically involves Friedel-Crafts acylation of phenol derivatives or aldol condensation reactions between appropriate aldehydes and ketones. The phenolic hydroxyl group can also be introduced or modified post-synthesis through selective hydroxylation reactions.

The compound has been studied for its potential biological activity and application as an intermediate in the synthesis of pharmaceuticals, fragrances, and other fine chemicals. The phenolic group contributes to antioxidant properties, while the ketone moiety provides a reactive site for chemical modification.

Physicochemical properties include moderate solubility in polar organic solvents such as ethanol and acetone, with limited solubility in water. The compound is generally a crystalline solid or viscous liquid depending on purity and specific conditions.

Analytical characterization is typically performed using nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry. The IR spectrum shows characteristic absorption bands for the phenolic O–H stretch and ketone C=O stretch near 1700 cm^-1.

In summary, 4-(4-hydroxyphenyl)-2-butanone is an aryl ketone with a phenolic substituent, combining reactive carbonyl and hydroxyl functional groups. Its chemical and physical properties make it a useful intermediate in organic synthesis and potential precursor in pharmaceutical and fragrance industries.

References

2023. Antioxidant Activity of Natural Phenols and Derived Hydroxylated Biphenyls. Molecules, 28(6).
DOI: 10.3390/molecules28062646

2023. Raspberry ketone ameliorates nonalcoholic fatty liver disease in rats by activating the AMPK pathway. European Journal of Pharmacology, 957.
DOI: 10.1016/j.ejphar.2023.176001

2024. Raspberry Ketone Prevents LPS-Induced Depression-Like Behaviors in Mice by Inhibiting TLR-4/NF-κB Signaling Pathway via the Gut-Brain Axis. Molecular Nutrition & Food Research, 68(10).
DOI: 10.1002/mnfr.202400090