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grapefruit nitrile
Grapefruit nitrile is a medium-strength citrus fragrance compound with woody notes, used primarily in perfumery for its fresh grapefruit scent and good substantivity.
General Material Description
Grapefruit nitrile, also known as khusinil (IFF proprietary name) and chemically identified as 2,2,4-trimethyl-4-phenylbutanenitrile, is a synthetic nitrile compound with the molecular formula C13H17N. It appears as a clear, colorless liquid and exhibits a characteristic citrus grapefruit odor combined with woody and green notes. This compound is notable in fragrance chemistry for imparting fresh, vibrant grapefruit-like accents with some complexity provided by its vetiver-like undertones. More information on its molecular structure and properties is available through the PubChem database. Grapefruit nitrile is typically produced through organic synthesis routes rather than extraction from natural sources, offering a consistent scent profile favored in fine fragrance applications.
Occurrence, Applicability & Potential Uses
While grapefruit nitrile does not naturally occur in significant biological sources, it is a valued synthetic fragrance ingredient recognized by fragrance industry standards such as FEMA (US). It is commonly employed to replicate citrus grapefruit notes complemented by woody undertones in perfumery and personal care products. Its usage enhances freshness in compositions requiring a medium-intensity citrus profile with good persistence. The compound's application is mostly confined to fragrance agents, contributing sparkle and bloom to complex aroma blends, especially those intended to evoke freshness and green citrus character while maintaining formulation stability.
Physico-Chemical Properties Summary
Grapefruit nitrile’s physicochemical profile includes a moderate boiling point range of 294 to 295°C at standard atmospheric pressure, indicating relatively low volatility among fragrance nitriles. Its vapor pressure is low (0.002 mmHg at 25°C), supporting prolonged fragrance substantivity estimated at 68 hours at 10% concentration in dipropylene glycol. The compound exhibits moderate lipophilicity with a logP value near 2.9, enabling good solubility in alcohol and limited aqueous solubility (~14.67 mg/L at 25°C). It has an estimated flash point of 230°F (approximately 110°C), allowing stable handling in typical industrial and formulation environments. Shelf life extends to about 24 months or more if stored protected from heat, light, and moisture.
FAQ
What is grapefruit nitrile and what are its main characteristics?
Grapefruit nitrile is a synthetic organic compound used primarily as a fragrance agent. Known chemically as 2,2,4-trimethyl-4-phenylbutanenitrile, it delivers a medium-strength citrus aroma reminiscent of grapefruit, accompanied by woody, green undertones. Its distinct scent profile includes fresh and slightly fruity notes, making it valuable for enhancing citrus themes in perfumes and personal care formulations. The compound appears as a clear liquid with moderate stability and low volatility.
How is grapefruit nitrile typically applied and where is it sourced from?
Grapefruit nitrile is widely utilized in perfumery to impart fresh grapefruit and woody citrus notes. It is incorporated into fragrance blends to add sparkle and lasting freshness, often at up to 10% concentration in fragrance concentrates according to IFRA (Global) guidelines. This compound is produced synthetically through organic chemical processes rather than extracted from natural sources, ensuring consistent purity and supply for industrial applications.
What safety and regulatory information is relevant to grapefruit nitrile?
Grapefruit nitrile carries hazard classifications under European regulations as harmful if swallowed and environmentally hazardous, particularly toxic to aquatic life with long-term effects. Safety measures recommend avoiding skin and eye contact and preventing environmental release. Its use is controlled by fragrance industry standards such as IFRA (Global), which sets limits on usage levels—for grapefruit nitrile, up to 10% in fragrance formulations is recommended, while it is not approved for flavor use. Comprehensive safety assessments are available, ensuring proper handling in industrial and consumer product contexts.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
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Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2926.90.0000 |
| ChemSpider: | View |
General Material Information
| Preferred name | grapefruit nitrile |
| Trivial Name | α,α,γ-Trimethylbenzenebutanenitrile |
| Short Description | khusinil (IFF) |
| Formula | C13 H17 N |
| CAS Number | 75490-39-0 |
| FDA UNII | Search |
| xLogP3-AA | 3.50 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 187.28549194336 |
| Boiling Point | 294 to 295°C @ 760 mm Hg |
| Vapor Pressure | 0.002 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.895 |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| water, 14.67 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Citrus | |
| citrus, gardenia, grapefruit, burnt, autumn, leafy, vetiver | |
| Odor strength | medium |
| Substantivity | 68 hour(s) at 10.00 % in dipropylene glycol |
| Luebke, William tgsc, (2009) | At 100.00 %. citrus gardenia grapefruit burnt autumn leaves vetiver |
| General comment | Adds sparkle and bloom to most compounds. Grapefruit, rhubarb, vetivert, green, woody |
| Arcadi Boix Camps, writing in 2009, when it was still a captive, tells us that it is “chemically related to Symrise’s Hydrocitronitrile but it smells totally different. It is extraordinarily citrussy-grapefruitlike with a torrent of freshness within its molecule.” | Citrus-grapefruit, fruity-rhubarb, woody, green, vetivert |
Potential Uses
| Applications | |
| Odor purposes | Citrus , Grapefruit , Woody |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xn N - Harmful, Dangerous for the environment. | |
| R 22 - Harmful if swallowed. R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for grapefruit nitrile usage levels up to: | |||
| 10.0000 % in the fragrance concentrate. | |||
| Recommendation for grapefruit nitrile flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):75490-39-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :156605 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2,2-dimethyl-4-phenylpentanenitrile |
| Chemidplus:0075490390 |