Aldehyde C16 EPG (Ethyl Phenyl Glycidate)

• 🏭 Manufacturer — IFF

• 🔎 Chemical name — ETHYL 3-PHENYLOXIRANE-2-CARBOXYLATE

• 📂 CAS N° — 121-39-1

• 📘 FEMA — 2454

• ⚖️ MW — 192.21 g/mol

• 📝 Odor type — Fruity

• 📈 Odor Strength — Medium

• 👃🏼 Odor Profile — Strong fruity aroma suggestive of strawberry

• ⚗️ Uses — Core strawberry note in fruity, gourmand, floral compositions. Blends well with ionones (violet), hydroxycitronellal, aldehydes, lactones (milky tones), and woody notes (Arctander, 1969).

Aldehyde C-16 (Ethyl Methylphenylglycidate) & Ethyl 3-Phenylglycidate (Aldehyce c16 EPG): A Comprehensive Overview

Introduction

The world of aroma chemicals contains many compounds with overlapping names but distinct properties. Two compounds often confused are Aldehyde C-16 (Ethyl Methylphenylglycidate, CAS 77-83-8) and Ethyl 3-Phenylglycidate (Strawberry Glycidate 2, CAS 121-39-1).

Both have been used in flavors and fragrances, but Aldehyde C-16 has a more established history in perfumery, while Ethyl 3-Phenylglycidate remains a niche molecule primarily used in research and flavor applications.

Aldehyde C-16 (Ethyl Methylphenylglycidate)

Historical Context

• Discovery (1903–1910s): The origins of Aldehyde C-16 trace back to the early 20th century with advancements in glycidic esters. It was first synthesized through a Darzens condensation reaction involving acetophenone and ethyl chloroacetate, creating a mixture of stereoisomers that contribute to its characteristic strawberry scent (Sell, 2006).

• Perfume and Flavor Adoption (1920s–1960s):

  • Lipstick and Cosmetics (1920s): Used to mask unpleasant base odors from castor oil and stearic acid in lipsticks, while imparting a pleasant fruity-jam note (Arctander, 1969).

  • Flavor Industry (1920s-1960s): Utilized in hard candies and confectionery before improved synthetic strawberry flavors became dominant (Perfumer & Flavorist, 2016).

• Impact of Chanel No. 5 (1921): Although Aldehyde C-16 was not directly used in Chanel No. 5, the fragrance's success popularized aldehydes, including those with fruity characteristics like C-16. This led to its increased use in perfumery (Edwards, 1997).

• Modern Applications (1970s–Present): Despite the decline in food applications, Aldehyde C-16 remains a key component in perfumery, valued for its sweet, fruity, strawberry-like character with floral and honeyed nuances (Good Scents Company, n.d.).

Chemical and Physical Properties

• CAS Number: 77-83-8

• Chemical Formula: C₁₂H₁₄O₃

• Molecular Weight: 206.24 g/mol

• Appearance: Clear, colorless to pale yellow liquid

• Odor: Strong, fruity, strawberry-like, with floral and honey undertones

• Boiling Point: 260–302°C

• Melting Point: Below -50°C

• Density: 1.09 g/mL at 25°C

• Flash Point: 131°C

• Refractive Index: 1.496–1.506 at 20°C

• Vapor Pressure: 0.00023 kPa at 20°C

Uses in Perfumery & Flavoring

• Fragrance Applications:

  • Core strawberry note in fruity, gourmand, floral compositions.

  • Blends well with ionones (violet), hydroxycitronellal, aldehydes, lactones (milky tones), and woody notes (Arctander, 1969).

• Flavor Industry:

  • Previously used in candies, gums, chocolates.

  • GRAS (Generally Recognized as Safe) for food use but less common today (FDA, 2021).

• Cosmetic Industry:

  • Found in lipsticks, body care, and soaps.

Safety and Regulatory Information

• GRAS Status: Recognized as safe by the U.S. FDA (FDA, 2021).

• Toxicity: Long-term studies show no carcinogenic effects (Good Scents Company, n.d.).

• Environmental Impact:

  • Low bioaccumulation (ECHA, 2023).

  • Toxic to aquatic life.

References

• Arctander, S. (1969). Perfume and Flavor Materials of Natural Origin. Allured Publishing.

• Edwards, M. (1997). Perfume Legends: French Feminine Fragrances. Crescent House Publishing.

• European Chemicals Agency (ECHA). (2023). Substance Information: Ethyl Methylphenylglycidate. Retrieved from https://echa.europa.eu

• FDA (U.S. Food and Drug Administration). (2021). GRAS Substances Database. Retrieved from https://www.fda.gov

• Good Scents Company. (n.d.). Ethyl Methylphenylglycidate Data Sheet. Retrieved from http://www.thegoodscentscompany.com

• Perfumer & Flavorist. (2016). An Aroma Chemical Profile: Ethyl Methyl Phenyl Glycidate. Retrieved from https://www.perfumerflavorist.com

• PubChem Database. (2023). Ethyl 3-Phenylglycidate Compound Information. Retrieved from https://pubchem.ncbi.nlm.nih.gov

• Sell, C. (2006). The Chemistry of Fragrances: From Perfumer to Consumer. Royal Society of Chemistry.