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1,4-dimethyl naphthalene
1,4-dimethyl naphthalene is an aromatic hydrocarbon with formula C12H12, known for a moldy, tarry flavor note and limited use outside fragrance and flavor industries.
General Material Description
1,4-dimethyl naphthalene is an aromatic hydrocarbon characterized by two methyl groups attached at positions 1 and 4 of the naphthalene ring system, yielding a molecular formula of C12H12. It appears as a colorless to pale yellow solid or liquid with a distinctive moldy, tar-like odor. Synonyms include 1,4-dimethylnaphthalene, 1,4-DMN, and naphthalene, 1,4-dimethyl-. This compound is indexed in controlled vocabularies such as the ChEBI database. It can be sourced synthetically or found as a minor constituent in certain natural products, including artemisia variabilis flower oil from Italy. Industrial and research interest is limited, with no common applications in flavor or fragrance formulation.
Occurrence, Applicability & Potential Uses
1,4-dimethyl naphthalene naturally occurs in low concentrations within some essential oils, notably artemisia variabilis flower oil from Italy at around 0.50%. While it has a distinctive moldy and tarry aroma, it is not used for commercial fragrance or flavor applications. Regulatory bodies such as REACH (European Union) recognize this compound primarily for information purposes rather than direct consumer product use. Its role is more significant in chemical research or as a reference standard rather than as a functional ingredient in formulation.
Physico-Chemical Properties Summary
The compound demonstrates a relatively high boiling point ranging from 267 to 268 °C at standard atmospheric pressure, supporting its thermal stability in moderate temperature processes. It possesses a specific gravity of approximately 1.016 at 25 °C and exhibits low vapor pressure (0.013 mmHg at 25 °C), indicating limited volatility. Its logP value of 4.37 signifies significant lipophilicity, influencing solubility characteristics and environmental partitioning. Soluble in alcohols but only sparingly soluble in water (~11.4 mg/L at 25 °C), these properties impact its handling and formulation constraints, especially in aqueous or hydro-alcoholic systems. The flash point is about 230 °F (approximately 110 °C), relevant for safety considerations during storage and processing.
FAQ
What is 1,4-dimethyl naphthalene and what are its key characteristics?
1,4-dimethyl naphthalene is an aromatic hydrocarbon containing two methyl groups attached to the naphthalene ring at positions 1 and 4, giving it the molecular formula C12H12. It is known for a moldy tar-like aroma and appears as a colorless or pale yellow substance. It is identified under synonyms such as 1,4-DMN and is cataloged in chemical databases like ChEBI. The compound is primarily used for informational and research purposes, with no common commercial use in fragrances or flavors.
Where does 1,4-dimethyl naphthalene naturally occur and how is it typically used?
This compound occurs naturally in certain plant essential oils, such as artemisia variabilis flower oil from Italy, where it constitutes around 0.50%. Despite its presence in natural sources, 1,4-dimethyl naphthalene is not employed in commercial fragrance or flavor formulations due to its moldy odor and limited desirable sensory attributes. Its primary value resides in chemical research settings and regulatory documentation rather than in applied product development.
What are the regulatory considerations and safety information for 1,4-dimethyl naphthalene?
Regulatory agencies including REACH in the European Union primarily list 1,4-dimethyl naphthalene for informational purposes without authorized use in food flavoring or cosmetic fragrances. Safety data indicate no classified hazards under OSHA's GHS system, with no established oral, dermal, or inhalation toxicity parameters. Usage recommendations specifically exclude this compound from fragrance and flavor categories. Relevant regulatory reviews and residue assessments are available through the European Food Safety Authority (EFSA). Comprehensive chemical safety summaries are accessible from sources such as Sigma-Aldrich and EPA databases.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 1,4-dimethylnaphthalene | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 11304 |
| Pubchem (sid): | 134976162 |
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 |
| CHEBI: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2902.90.9000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 1,4-dimethyl naphthalene |
| Trivial Name | 1,4-Dimethylnaphthalene |
| Short Description | naphthalene, 1,4-dimethyl- |
| Formula | C12 H12 |
| CAS Number | 571-58-4 |
| ECHA Number | 209-335-9 |
| FDA UNII | BQH3S1I0SO |
| Nikkaji Number | J116.786C |
| Beilstein Number | 2039842 |
| MDL | MFCD00004037 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 156.22764587402 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Boiling Point | 267 to 268°C @ 760 mm Hg |
| Vapor Pressure | 0.013 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 4.37 |
| Solubility | |
| alcohol | Yes |
| water, 11.4 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Flavor Type: Moldy | |
| moldy, resinous | |
| General comment | Mouldy tarry |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| 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: | |||
| information only not used for fragrances or flavors | |||
| Recommendation for 1,4-dimethyl naphthalene usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for 1,4-dimethyl naphthalene flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| European Food Safety Authority (EFSA) reference(s): |
| Conclusion on the peer review of the pesticide risk assessment of the active substance 1,4-dimethylnaphthalene View page or View pdf |
| Reasoned opinion on the setting of a new MRL for 1,4-dimethylnaphthalene in potatoes View page or View pdf |
| Outcome of the consultation with Member States, the applicant and EFSA on the pesticide risk assessment for 1,4-dimethylnaphthalene in light of confirmatory data View page or View pdf |
| Review of the existing maximum residue levels for 1,4-dimethylnaphthalene according to Article 12 of Regulation (EC) No 396/2005 View page or View pdf |
| 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 :11304 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 1,4-dimethylnaphthalene |
| Chemidplus:0000571584 |