Anisyl Phenylacetate: Properties, Uses & Lab Guide
Anisyl Phenylacetate: Properties, Uses & Lab Guide
Anisyl phenylacetate is an aromatic ester formed from anisyl alcohol (4-methoxybenzyl alcohol) and phenylacetic acid, valued in fragrance research and flavour science for its characteristic floral–honey aroma profile.
- Chemical Name
- 4-Methoxybenzyl phenylacetate (Anisyl phenylacetate)
- CAS Number
- Needs verification — flag for review
- Molecular Formula
- C₁₆H₁₆O₃
- Molecular Weight
- 256.30 g/mol
- Appearance
- Colourless to pale yellow liquid or solid
- Aroma Character
- Floral, honey-like, rose nuance
- Aladdin SKU
- A464228
Chemical Identity and Structure
Anisyl phenylacetate is an ester formed by the condensation of 4-methoxybenzyl alcohol (anisyl alcohol) with phenylacetic acid. Its systematic name is 4-methoxybenzyl phenylacetate, and it belongs to the broader class of benzylic esters widely encountered in natural flavour and fragrance chemistry. The molecule contains a methoxy-substituted benzyl group on the alcohol side and a phenylacetyl moiety on the acid side, giving rise to its distinctive dual-aromatic character. The molecular formula is C₁₆H₁₆O₃ with a molecular weight of approximately 256.30 g/mol. The ester linkage (–COO–) confers moderate polarity, making the compound miscible with common organic solvents such as ethanol, diethyl ether, and ethyl acetate, while being sparingly soluble in water.
Fragrance and Flavour Applications
Anisyl phenylacetate is primarily employed as a fragrance ingredient and flavour research standard. Its organoleptic profile is typically described as floral, honey-like, and rose-nuanced, which makes it a useful component in formulating fine fragrances, functional fragrances (e.g., fabric softeners, detergents), and food flavour systems. In research settings, it serves as a reference compound for studying ester biosynthesis, enzymatic hydrolysis, and structure–odour relationships. The compound may occur naturally in trace amounts in certain floral essential oils, though commercial supplies are generally produced by chemical synthesis. Regulatory acceptance for use in food and cosmetic applications varies by jurisdiction and should be confirmed against current IFRA, EU, or FDA guidelines before formulation use.
Laboratory Handling and Storage
When working with anisyl phenylacetate in the laboratory, standard precautions applicable to aromatic organic esters should be observed. The compound should be stored in a tightly sealed container, protected from light and moisture, at cool room temperature or under refrigeration (2–8 °C) to maintain purity and prevent hydrolysis. Adequate ventilation or a fume hood is recommended when handling the neat material, as concentrated aromatic esters can cause sensory irritation at high vapour concentrations. Personal protective equipment including nitrile gloves, safety glasses, and a lab coat should be worn. Spills should be absorbed with an inert material and disposed of in accordance with local regulations for organic solvents and fragrance chemicals. Researchers should consult the product-specific Safety Data Sheet (SDS) for detailed hazard classifications, first-aid measures, and disposal guidance prior to use.
Analytical Characterisation Methods
Anisyl phenylacetate can be characterised by several standard analytical techniques. Gas chromatography–mass spectrometry (GC-MS) is the most common approach for identity confirmation and purity assessment, using a non-polar or mid-polar capillary column with electron ionisation detection; characteristic fragment ions arise from cleavage of the ester bond and loss of the methoxybenzyl or phenylacetyl groups. High-performance liquid chromatography (HPLC) with UV detection (λ ≈ 254–280 nm) is suitable for quantitative analysis in complex matrices. Nuclear magnetic resonance (NMR) spectroscopy (¹H and ¹³C) provides definitive structural confirmation: the methoxy singlet appears near δ 3.8 ppm, the benzylic –OCH₂– protons near δ 5.1 ppm, and the phenylacetyl –CH₂– near δ 3.6 ppm in ¹H NMR. Infrared spectroscopy (IR) shows a strong ester carbonyl absorption near 1735 cm⁻¹. Refractive index measurement can serve as a rapid purity check for liquid samples.
Frequently asked questions
What is anisyl phenylacetate used for in research?
Anisyl phenylacetate is used primarily as a fragrance reference standard and flavour chemistry research compound. It is also employed in studies of ester synthesis, enzymatic biotransformation, and structure–odour relationships in olfactory research.
How should anisyl phenylacetate be stored to maintain stability?
The compound should be stored in a tightly sealed, light-resistant container at cool room temperature or under refrigeration (2–8 °C). Exposure to moisture, heat, and light should be minimised to prevent hydrolysis and degradation of the ester bond.
Which analytical technique is best for confirming the identity of anisyl phenylacetate?
GC-MS is the most widely used technique for identity confirmation and purity assessment of anisyl phenylacetate, providing characteristic mass spectral fragmentation patterns. Complementary ¹H NMR spectroscopy offers definitive structural verification.
Is anisyl phenylacetate the same compound listed as Sigma-Aldrich W374008?
The source material references Sigma catalogue number W374008 as an associated identifier for anisyl phenylacetate. Researchers should cross-reference the CAS number and molecular formula to confirm equivalence before substituting suppliers.
References
- Sigma-Aldrich product page for Anisyl phenylacetate, catalogue number W374008. Merck KGaA.
- Burdock, G.A. (Ed.). Fenaroli's Handbook of Flavor Ingredients, 6th ed. CRC Press, 2010. (General reference for flavour ester properties and regulatory status.)
- International Fragrance Association (IFRA). IFRA Standards and Guidelines. (Regulatory framework for fragrance ingredient use.)
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