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5-(methyl thio) valeronitrile
5-(methyl thio) valeronitrile is an organosulfur nitrile found naturally in mustard seeds, noted for its cabbage-like odor and application in natural extractive substances.
General Material Description
5-(methyl thio) valeronitrile is classified as an organosulfur nitrile compound with the molecular formula C6H11NS. It appears as a volatile liquid and exhibits a distinctive odor reminiscent of cabbage and broccoli when diluted at 0.10% in dipropylene glycol. Known under various synonyms including 5-(methylthio)pentanenitrile and 5-methylsulfanylpentanenitrile, this substance is documented in chemical databases such as PubChem (CID 93320). It principally occurs in natural botanical sources like mustard and field mustard seeds, where it contributes to characteristic aroma profiles. The compound’s sensory properties and natural occurrence make it relevant for studies in natural extractives and flavor chemistry.
Occurrence, Applicability & Potential Uses
5-(methyl thio) valeronitrile naturally occurs in mustard seeds and field mustard plants, contributing to their sulfurous and cabbage-like aroma. It is associated with natural substances and extractives, predominantly explored for its organoleptic characteristics rather than direct commercial use. According to FEMA (US) guidelines relevant to flavor ingredient evaluation, this compound is not recommended for use in food flavorings or fragrances due to limited toxicological data. However, it remains of interest in analytical research and profiling of volatile sulfur compounds in plant materials. The compound's occurrence underscores its role in botanical aroma and its potential as a marker compound in natural product chemistry.
Physico-Chemical Properties Summary
5-(methyl thio) valeronitrile features a molecular weight of approximately 129.23 g/mol and a moderate estimated partition coefficient (logP) of 1.125, indicating balanced lipophilicity that affects its interaction within formulations. It has a boiling point range of 241 to 242°C at atmospheric pressure (760 mm Hg), reflecting relatively low volatility compared to lighter sulfur compounds. The compound’s vapor pressure at 25°C is low, about 0.037 mm Hg, supporting reduced evaporation under ambient conditions. It is soluble in alcohols and has moderate water solubility estimated at 3117 mg/L at 25°C. A flash point near 211°F (99.4°C) suggests standard handling precautions for flammable liquids. These physicochemical properties influence its behavior in mixtures, impacting extraction, sensory release, and stability.
FAQ
What is 5-(methyl thio) valeronitrile and where is it found?
5-(methyl thio) valeronitrile is an organosulfur nitrile compound characterized by a cabbage-like odor. It occurs naturally in mustard seeds and field mustard plants as part of their volatile organic components. This compound contributes to the sulfurous aroma typical of these plant sources. Its chemical structure includes a nitrile functional group and a methylthio substituent, and it is a subject of interest for natural extractive research.
How is 5-(methyl thio) valeronitrile used and what are its main properties?
The primary use of 5-(methyl thio) valeronitrile is in natural substances and extractives research rather than commercial flavor or fragrance applications. It features a moderate boiling point around 241 to 242°C and low vapor pressure at room temperature, indicating limited volatility. The compound is moderately soluble in alcohol and water, facilitating extraction and analytical applications. Its distinctive cabbage-like odor is notable in sensory evaluations of mustard-related materials.
What regulatory or safety information is associated with 5-(methyl thio) valeronitrile?
According to current data, 5-(methyl thio) valeronitrile has no classified hazards under OSHA’s Hazard Communication Standard (29 CFR 1910). It is recommended not for use in flavor or fragrance formulation according to natural substance usage guidelines. Toxicological profiles, including oral, dermal, and inhalation toxicity, have not been fully determined. Safety assessments should refer to authoritative databases such as EPA’s Substance Registry Services and PubChem for updates.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 5-methylsulfanylpentanenitrile | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 93320 |
| Pubchem (sid): | 135051217 |
| Flavornet: | 59121-25-4 |
| Publications by PubMed | |
| 4-Methylthio-butanyl derivatives from the seeds of Raphanus sativus and their biological evaluation on anti-inflammatory and antitumor activities. | |
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 |
| FooDB: | FDB029658 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 5-(methyl thio) valeronitrile |
| Trivial Name | 5-(Methylthio)pentanenitrile |
| Short Description | pentanenitrile, 5-(methylthio)- |
| Formula | C6 H11 N S |
| CAS Number | 59121-25-4 |
| FDA UNII | Search |
| Nikkaji Number | J45.902J |
| xLogP3-AA | 1.30 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 129.22567749023 |
| Boiling Point | 241 to 242°C @ 760 mm Hg |
| Vapor Pressure | 0.037 mmHg @ 25 °C |
| Flash Point TCC Value | 99.6 °C TCC |
| logP (o/w) | 1.125 est |
| Solubility | |
| alcohol | Yes |
| water, 3117 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Cabbage | |
| broccoli, cabbage | |
| General comment | At 0.10 % in dipropylene glycol. broccoli cabbage |
Occurrences
| (data available) |
Safety Information
Safety information
| 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: | |||
| natural substances and extractives | |||
| Recommendation for 5-(methyl thio) valeronitrile usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for 5-(methyl thio) valeronitrile flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :93320 |
| National Institute of Allergy and Infectious Diseases:Data |
| 5-methylsulfanylpentanenitrile |
| Chemidplus:0059121254 |