Stemone ®

Stemone® (22457-23-4) - TECHNICAL INGREDIENT OVERVIEW

• 🏭 Manufacturer — Givaudan

• 🔎 Chemical Name — (NZ)-N-(5-methylheptan-3-ylidene)hydroxylamine

• 🧪 Synonyms — Stemone®, 5-methyl-3-heptanone oxime, ethyl 2-methylbutyl ketoxime, leafy oxime, greenone, heptoxime

• 🧬 Chemical Formula — C₈H₁₇NO

• 📂 CAS Number — 22457-23-4

• 📘 FEMA Number — Not listed (not approved for food use)

• ⚖️ Molecular Weight — 143.23 g/mol

• 📝 Odor Type — Green, leafy, natural

• 📈 Odor Strength — Medium to strong

• 👃🏼 Odor Profile — Green, fruity-fig, leafy, fresh, vegetal, natural, tomato stem, blackcurrant bud

• ⚗️ Uses — Enhances green top notes in floral, fruity, and citrus compositions; fig and tomato leaf accords; naturalistic reconstructions; lily-of-the-valley, narcissus, and mandarin accords

• 🧴 Appearance — Colorless to pale yellow liquid

• 🌡️ Boiling Point — 70°C at 0.1 kPa (0.75 mmHg)

• 🔬 Refractive Index — n²⁰D 1.4519

What is Stemone®?

Stemone® is a synthetic fragrance molecule belonging to the oxime family, specifically designed to deliver a hyper-realistic green and leafy scent profile. Chemically, it's a low molecular weight oxime compound featuring a hydroxylamine functional group that forms a stable imine structure—this is what gives Stemone® its distinctive crushed stem and fig leaf character (Givaudan, n.d.).

Originally developed and patented by Givaudan, one of the world's leading fragrance houses, Stemone® has become a cornerstone ingredient in modern green perfumery. Its ability to capture the fresh, verdant smell of living plants—particularly fig leaves, tomato stems, and blackcurrant buds—makes it invaluable for perfumers seeking naturalistic effects that are difficult to achieve with natural extracts alone (Fragrantica, 2015).

Unlike many synthetic molecules that smell "chemical" or artificial, Stemone® delivers an authentic botanical quality that adds depth and realism to fragrance compositions, making it especially popular in contemporary niche perfumery.

Historical Background

Stemone® was discovered and developed by Givaudan in 1967, marking a significant milestone in the company's innovation in green fragrance materials. During this period, the fragrance industry was actively exploring new synthetic routes to recreate natural plant scents with greater precision and stability than what natural extracts could offer.

The molecule emerged from Givaudan's research into oxime chemistry—a class of compounds formed by the reaction of ketones with hydroxylamine. Perfumers quickly recognized Stemone®'s unique ability to evoke the smell of crushed green stems and fig leaves, an olfactory impression that was previously challenging to achieve synthetically.

According to Hervé Fretay, Givaudan's Global Director of Naturals and Fragrance Ingredient Marketing, Stemone® joined other iconic Givaudan discoveries like Undecavertol as a pioneering green note material (Fragrantica, 2015). Over the past five decades, it has become a standard tool in perfumers' palettes worldwide, valued for its power to modernize and naturalize green accords across all fragrance categories.

The molecule's commercial success led to its adoption beyond Givaudan, with the ingredient now available from multiple suppliers serving the global fragrance industry.

Olfactory Profile

Scent Family

Stemone® belongs to the Green fragrance family, with strong Leafy-Vegetal and Fruity-Fresh subfacets.

Main Descriptors

• Primary: Green, leafy, natural, fresh

• Secondary: Fig leaf, tomato stem, blackcurrant bud

• Tertiary: Fruity-sweet undertone, crushed stems, herbaceous

The scent captures the moment of crushing fresh green plant material between your fingers—vivid, sappy, and alive. It balances sharp green freshness with a smooth, slightly sweet fruitiness that prevents it from becoming too harsh or metallic.

Intensity

Medium to strong. Stemone® is highly potent and diffusive, meaning a little goes a long way. Even at low concentrations (0.1-0.5%), it noticeably lifts and brightens a composition. At higher doses (0.5-1%), it dominates with its distinctive green character.

Tenacity

Low to medium. As a top note material, Stemone® evaporates relatively quickly, typically lasting 2-4 hours on a blotter. However, its impact during the opening phase is memorable and diffusive.

Volatility

Top note material with high volatility. Its low molecular weight (143.23 g/mol) and vapor pressure (0.0427 hPa) mean it evaporates rapidly, making it perfect for creating fresh, immediate impressions in the opening of a fragrance (Givaudan, n.d.).

Applications in Fine Fragrance

Stemone® serves as a powerful modifier and enhancer in modern perfumery, particularly valued for its ability to add naturalistic freshness to synthetic-heavy structures. Its key applications include:

• Green-Floral Accords: Enhances lily-of-the-valley, narcissus, and violet compositions with a natural leafy facet

• Citrus Fragrances: Modernizes mandarin, grapefruit, and bergamot openings with green vibrancy

• Fig Compositions: Essential for realistic fig leaf reconstructions when combined with coconut lactones and orris notes

• Fruity Blends: Adds natural depth to blackcurrant, raspberry, and pear accords

• Fresh Fougères: Brings botanical realism to aromatic and herbal structures

Stemone® pairs exceptionally well with other green materials like galbanum, violet leaf, and cis-3-hexenol, as well as with fresh aldehydes and citrus oils. It's especially effective in transparent, natural-smelling compositions where authenticity is paramount.

Performance in Formula

In fragrance formulations, Stemone® behaves predictably and blends smoothly with both natural and synthetic ingredients. Key performance characteristics include:

• Dosage: Typically used at 0.1-1% in the finished fragrance concentrate; trace amounts (0.05-0.1%) provide freshening effects, while 0.5-1% delivers a distinct green signature

• Stability: Stable in alcoholic solutions and most cosmetic bases; avoid use in formulations containing bleach or strong oxidizers

• Blending: Mixes easily with aldehydes, esters, terpenes, and essential oils; can become metallic if overused or paired with certain synthetic musks

• Effect on Structure: Adds transparency and lift to heavy florals; brings naturality to synthetic bouquets; can thin out overly dense compositions

Synthesis Note: Stemone® is produced by oximation of 5-methyl-3-heptanone (the corresponding ketone) with hydroxylamine. The molecule contains an asymmetric carbon and a double bond, which creates four possible stereoisomers. The commercial material used in perfumery is a mixture of these isomers, and it is this specific blend that delivers the characteristic green-leafy profile (Common Fragrances & Flavour Materials, 2002).

Natural Occurrence: Stemone® does not occur in nature and cannot be isolated from botanical sources. Its synthetic origin allows for consistent quality and availability compared to natural green materials like fig leaf absolute, which shares similar olfactory characteristics but is produced in very limited quantities (typically under 200 kg annually) through solvent extraction of Ficus carica leaves (Arctander, 1960).

Note: While Stemone® has good stability in most bases, its top-note volatility means it will naturally dissipate over time in the wear-down of a fragrance.

Industrial & Technical Uses

Stemone® is exclusively used in fragrance applications and is not approved for flavoring or food contact. Its primary industrial applications include:

• Fine Fragrances: Eau de parfum, eau de toilette, and cologne formulations

• Functional Perfumery: Shampoos, shower gels, body lotions, and soaps

• Home Care: Laundry detergents, fabric softeners, and household cleaning products

• Scented Products: Candles and air fresheners (limited due to high volatility)

The molecule's chemistry makes it particularly useful in alkaline formulations typical of many personal care and home care products, where it maintains its green character even in challenging pH conditions.

Regulatory & Safety Overview

1. IFRA Status: Stemone® (CAS 22457-23-4) is not restricted under the IFRA Standards up to and including the 51st Amendment (January 2024). It is approved for unrestricted use in all fragrance product categories without maximum allowable concentration limits (IFRA, 2024; https://ifrafragrance.org/safe-use/standards-documentation).

2. EU Cosmetics Regulation: Not listed among the 26 declarable allergens under EU Regulation (EC) No 1223/2009. No special labeling requirements.

3. FEMA GRAS Status: Not listed. Stemone® is not approved for use in food, beverages, or flavorings.

4. REACH Registration: Registered under the European Chemicals Agency (ECHA). Not classified as hazardous under CLP regulation.

5. Toxicology: Safety assessments indicate low skin irritation and non-sensitizing properties at typical use concentrations. No known phototoxicity. No evidence of genotoxicity or reproductive toxicity in standard testing protocols (ECHA, n.d.).

6. Usage Recommendations: Follow Good Manufacturing Practices (GMP). Use appropriate personal protective equipment when handling concentrated material. Store in closed containers away from heat and oxidizing agents.

   
   

   ✅ Stemone® is approved for unrestricted use in perfumery and complies with global fragrance safety standards.

References

• Arctander, S. (1960). Perfume and flavor materials of natural origin. Published by the author.

• Common Fragrances & Flavour Materials. (2002). In H. Surburg & J. Panten (Eds.), Common fragrance and flavor materials: Preparation, properties and uses (5th ed.). Wiley-VCH.

• European Chemicals Agency (ECHA). (n.d.). Substance information: CAS 22457-23-4. Retrieved from https://echa.europa.eu/

• Fragrantica. (2015). What fragrances are made of: Givaudan, Part 3 [Interview with Hervé Fretay]. Retrieved from https://www.fragrantica.com/news/What-Fragrances-Are-Made-of-Givaudan-Part-3-6861.html

• Givaudan. (n.d.). Stemone™ technical documentation. Givaudan Fragrance Ingredients Business.

• International Fragrance Association (IFRA). (2024). IFRA Standards – 51st Amendment. Retrieved from https://ifrafragrance.org/safe-use/standards-documentation

• National Center for Biotechnology Information (NCBI). (n.d.). PubChem Compound Summary for CID 86289010, Stemone. Retrieved from https://pubchem.ncbi.nlm.nih.gov/