Phenirat

Phenirat® (103-60-6) Technical Ingredient Overview

• 🏭 Manufacturer — Symrise (also produced by other major fragrance houses including H&R, Takasago)

• 🔎 Chemical Name — 2-Phenoxyethyl 2-methylpropanoate (2-Phenoxyethyl isobutyrate)

• 🧪 Synonyms — Phenirat®, Phenoxyethyl isobutyrate, Ethylene glycol monophenyl ether isobutyrate, Beta-Phenoxyethyl iso-butyrate, Phenylcellosolve isobutyrate

• 📂 CAS Number — 103-60-6

• 📘 FEMA Number — 2873 (GRAS status for flavor use)

• ⚖️ Molecular Weight — 208.25-208.26 g/mol

• 🧬 Chemical Formula — C₁₂H₁₆O₃

• 📝 Odor Type — Green (with pronounced fruity-floral character)

• 📈 Odor Strength — Medium intensity with good tenacity

• 👃🏼 Odor Profile — Sweet, fruity-floral with rose, honey, and ripe fruit character; light green undertone; apple, pear, and kiwi nuances; pastry-like sweetness

• 👅 Flavor Profile — Pear, apple, kiwi, honey, sweet fruity-tropical notes; green, pastry undertones

• ⚗️ Uses — Floral-fruity modifier, tropical fruit enhancer, raspberry and pear booster, rose and lavender fixative, specialty blends

• 🧴 Appearance — Clear, colorless to pale yellow mobile liquid

What is Phenirat®?

Phenirat® (2-Phenoxyethyl isobutyrate) is a synthetic aromatic ester created through the esterification of 2-phenoxyethanol (ethylene glycol monophenyl ether) with isobutyric acid. This process, typically conducted in the presence of boric acid in benzene solution or using other acid catalysts, yields a versatile fragrance material that has found extensive application across both perfumery and flavor industries (Surburg & Panten, 2006).

Structurally, Phenirat® combines a phenoxyethyl alcohol backbone with an isobutyric acid moiety, resulting in a compound with moderate volatility and smooth diffusion characteristics. This molecular architecture contributes to its unique ability to bridge green, floral, and fruity olfactory notes in a naturalistic manner, making it ideal for nuanced layering in complex compositions.

Despite being classified as a "green" fragrance material, Phenirat® presents a surprisingly rounded and honeyed character with distinct rose and ripe fruit associations. This unexpected olfactory complexity makes it far more versatile than its simple structural formula might suggest. The compound belongs to the fragrance structural group known as Aryl Alkyl Alcohol Simple Acid Esters (AAASAE), which are characterized by excellent stability and broad compatibility with other perfumery materials.

Phenirat® has not been reported to occur in nature; all commercial material is synthetic. The worldwide annual usage volume falls in the range of 100-1,000 metric tons, indicating its significant commercial importance (IFRA, 2008).

Historical Background

Phenirat® emerged during the mid-20th century expansion of synthetic ester chemistry for perfumery applications. While the exact date of its first commercial introduction is not precisely documented, the material gained prominence in the 1950s-1960s as perfumers sought versatile fruity-floral modifiers that could function as both fixatives and top-note enhancers.

The name "Phenirat" is derived from "phenoxy" (referring to its phenoxyethanol backbone) and likely the manufacturer's designation, with H&R (Haarmann & Reimer, now part of Symrise) being credited with the Phenirat® tradename in the literature.

Steffen Arctander, in his comprehensive work on perfume materials, described Phenirat® with notable enthusiasm, characterizing it as having a "sweet-fruity, rosy-floral, slightly honey-like odor of excellent tenacity." He expressed surprise that many perfume laboratories of his era did not stock this material, noting that "its odor type should place it among the most frequently used materials for daily use in fragrances for household products, soaps, detergents, room sprays, etc." (Arctander, 1969).

The compound's dual utility in both perfumery and flavoring led to its inclusion in the FEMA GRAS list (FEMA 2873) and approval by the Joint FAO/WHO Expert Committee on Food Additives (JECFA 1028), cementing its status as a safe and versatile aromatic ester across multiple applications.

In contemporary perfumery, Phenirat® continues to serve as a valuable tool for perfumers working with fruit-forward compositions, modern florals, and functional fragrances where its non-overpowering character and moderate tenacity provide controlled sensory enhancement without dominating the composition.

Olfactory Profile

Scent Family: Fruity-Floral / Green-Rosy

Main Descriptors:

• Top notes: Sweet, fruity opening with fresh green apple and pear character; light, airy floral hints

• Heart notes: Rosy-floral softness emerges; honey-like sweetness develops; kiwi and ripe fruit nuances; powdery fruit blossom aspects

• Base notes: Gentle persistence with pastry-like warmth; subtle green undertone provides freshness throughout

Intensity: Medium odor strength; non-overpowering and easy to work with in precise formulations

Tenacity: Excellent for an ester of this type; provides lasting radiance and fixative support, particularly in rose and lavender compositions

Volatility: Moderate volatility with smooth diffusion; boiling point at 182°C (at 0.53 kPa: 125-127°C); functions primarily as top-to-heart note material

Character: Despite its "green" classification, Phenirat® reads as predominantly fruity-floral with honeyed sweetness. The greenness manifests as freshness rather than sharp herbal notes, providing lift without creating harsh top notes

Related Scentspiracy Materials

Explore complementary fruity-floral and rosy materials:

• Phenylethyl Acetate - Rosy-fruity ester with honey-like character

• Phenyl Ethyl Alcohol - Classic rose-scented compound

• Methyl Phenylacetate - Powerful honey-floral with jasmine nuances

• Phenyl Hexanol (Phenoxanol) - Tenacious white-floral with rose-muguet character

Applications in Fine Fragrance

Phenirat® serves multiple essential functions in modern perfumery:

Primary Applications:

• Rose accords: Functions as both a modifier and fixative, adding fruity sweetness and honey notes while enhancing tenacity

• Lavender compositions: Provides soft floral-fruity roundness and fixative properties

• Fruity-floral blends: Essential for creating naturalistic raspberry, pear, kiwi, and apple accords

• Tropical fruit profiles: Adds juiciness and complexity to exotic fruit compositions

• Honeyed fantasy notes: Contributes sweet, pastry-like warmth to gourmand and floral-fruity hybrids

• Green-floral accords: Bridges fresh green notes with soft floral warmth

Notable Pairings:

• Raspberry ketone: Enhances juiciness and berry character

• Ionones (alpha and beta): Creates beautiful floral-violet bridges

• DMBC Butyrate: Adds sweet-tropical complexity

• Phenylethyl alcohol: Reinforces rosy character with additional depth

• Floral alcohols: Works harmoniously with geraniol, citronellol, linalool

• Green materials: Complements cis-3-hexenol, galbanum, violet leaf notes

Typical Usage Levels:

• Fine fragrance: 0.5-3% in perfume compound

• Functional fragrances: Up to 5% in body sprays, haircare, fabric softeners

• Minimalist compositions: Can be used at lower levels (0.1-0.5%) for subtle fruit enhancement

Performance in Formula

Phenirat® exhibits excellent formulation characteristics:

Physical Properties:

• Density: 1.045-1.049 g/mL at 20°C

• Refractive index: nD²⁰ 1.4920-1.4950

• Boiling point: 182°C (at 0.53 kPa: 125-127°C)

• Flash point: 110°C

• Optical rotation: 0° (not optically active)

• Assay: >98% (GC purity)

• Acid value: <1 mg KOH/g

Solubility & Compatibility:

• Insoluble in water

• Readily soluble in ethanol and most organic solvents

• Excellent compatibility with other perfumery materials

• Stable in alcohol-based and oil-based formulations

Stability Profile:

• Good oxidative stability

• Stable under standard storage conditions

• No significant photodegradation issues

• Maintains quality for >24 months when properly stored

Storage Recommendations:

• Keep in tightly closed containers

• Store in cool, dry place protected from light

• Check quality before use if stored >24 months

Industrial & Technical Uses

Beyond fine fragrance, Phenirat® finds versatile application across multiple industries:

Perfumery Applications:

• Fine fragrances (fruity-florals, tropical florals, modern chypres)

• Functional perfumery (body sprays, shampoos, conditioners)

• Household products (fabric softeners, detergents, room sprays)

• Soap perfumes (bar soaps, liquid soaps)

Flavor Industry (FEMA 2873):

• Fruit flavoring: Pear, apple, kiwi, tropical fruit profiles

• Confectionery: Honey and pastry notes

• Beverages: Fruity-sweet enhancement

• Typical usage: Low ppm ranges due to potency

Cosmetics & Personal Care:

• Acts as emollient and skin-conditioning agent

• Enhances texture and moisture retention in lotions and creams

• Provides pleasant fragrance in leave-on products

Pharmaceutical Applications:

• Used as solvent and carrier in some drug formulations

• Improves solubility and bioavailability of active ingredients

Regulatory & Safety Overview

IFRA Status:

• Permitted for use in all fragrance applications

• Usage levels based on category-specific guidance

• No specific restrictions under IFRA Amendment 51

• Member of the Aryl Alkyl Alcohol Simple Acid Esters (AAASAE) structural group

EU Cosmetics Regulation 1223/2009:

• Not listed among the 26 declarable allergens

• EINECS Number: 203-127-1

• Compliant for use in cosmetic products

• Hazard classification: H402 - Harmful to aquatic life (minor environmental concern)

FEMA GRAS Status:

• FEMA Number 2873: Generally Recognized As Safe for flavor use under controlled limits

• JECFA Number 1028: Approved by Joint FAO/WHO Expert Committee

• 21CFR172.515: Listed in U.S. Code of Federal Regulations

ECHA (REACH) Registration:

• Registered substance under EU REACH

• Not classified as hazardous under CLP (Classification, Labelling and Packaging) regulation

• PubChem ID: 61005

• MDL Number: MFCD00027363

Safety Profile:

• Low toxicity by ingestion and skin contact

• Non-sensitizing at typical use levels in fragrance applications

• No evidence of skin irritation in standard testing protocols

• No phototoxicity observed

• Genotoxicity: Negative in standard battery of tests

• Repeated dose studies: No adverse effects at relevant exposure levels

• UV absorption: Minor absorption at 250-280 nm; peaks at 200 and 220 nm

Environmental Considerations:

• Classified as harmful to aquatic life (H402)

• Worldwide usage: 100-1,000 metric tons per year

• Proper disposal and environmental management recommended

References

• Arctander, S. (1969). Perfume and flavor materials of natural origin. Published by the author.

• International Fragrance Association (IFRA). (2008a). Use level survey. December 2008.

• International Fragrance Association (IFRA). (2008b). Volume of use survey. September 2008.

• Research Institute for Fragrance Materials (RIFM). (2012). Fragrance material review on 2-phenoxyethyl isobutyrate. Food and Chemical Toxicology, 50(Suppl. 2), S65-S73. https://doi.org/10.1016/j.fct.2011.11.046

• Surburg, H., & Panten, J. (2006). Common fragrance and flavor materials: Preparation, properties and uses (5th ed.). Weinheim: Wiley-VCH. https://doi.org/10.1002/3527608214

• WHO Food Additives Series No. 50. (2003). Safety evaluation of certain food additives and contaminants prepared by the fifty-ninth meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA).