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4-methyl biphenyl
4-methyl biphenyl is an aromatic biphenyl compound with spicy and floral sensory properties, primarily used as a flavoring agent in various food products.
General Material Description
4-methyl biphenyl is an aromatic organic compound classified as a substituted biphenyl, with the molecular formula C13H12. It appears as a colorless to pale liquid or solid, depending on conditions. The compound is noted for its distinctive sensory characteristics, exhibiting spicy, floral, wintergreen, and minty odor and flavor profiles. It is also known by several synonyms including p-methylbiphenyl, 4-methyl diphenyl, and para-methyl phenyl benzene. This compound is referenced in established chemical databases such as PubChem, where detailed physicochemical and safety data are available. 4-methyl biphenyl is commonly obtained through synthetic chemical processes designed to introduce a methyl group at the para-position of the biphenyl structure and is largely used in flavor applications.
Occurrence, Applicability & Potential Uses
Although 4-methyl biphenyl is not typically sourced from natural biological origins, it is widely utilized as a flavoring agent in the food industry. The compound contributes characteristic spicy and minty notes, making it suitable for incorporation into chocolate, herbal products, licorice, mint, and wintergreen flavors. Its designation under the FEMA (US) system as flavoring substance number 3186 confirms its acceptance in flavor formulations. This compound's ability to enhance specific sensory attributes is also leveraged in various beverages and confectionery products. Regulatory evaluations, including those by JECFA and EFSA (EU), support its controlled use within established exposure limits to ensure consumer safety.
Physico-Chemical Properties Summary
4-methyl biphenyl exhibits a melting point between 49 and 50°C and a boiling range of approximately 267 to 268°C at standard atmospheric pressure of 760 mm Hg. Its vapor pressure at 25°C is low, measured at 0.013 mmHg, indicating moderate volatility. The compound's flash point is approximately 230°F (about 110°C). It has a relatively high logP value of 4.63, reflecting its lipophilicity and likely low solubility in water, although some solubility is reported around 4 to 7 mg/L at 25°C. The substance is soluble in alcohols, making it amenable to incorporation in various formulations. These properties influence its handling, storage, and performance in flavor delivery systems, particularly under thermal processing conditions.
FAQ
What is 4-methyl biphenyl and what are its main characteristics?
4-methyl biphenyl is a methyl-substituted biphenyl compound with the formula C13H12. It presents aromatic properties with spicy, floral, and minty sensory notes. Often used as a flavoring agent, it is recognized by several synonyms including p-methylbiphenyl and para-methyl diphenyl. Its texture and appearance may vary with temperature, typically a colorless liquid or solid, depending on the state.
How and where is 4-methyl biphenyl used industrially?
This compound is primarily employed as a flavoring agent in the food and beverage industry. Its spicy and wintergreen notes make it suitable for flavoring chocolate, herbal products, licorice, mint, and wintergreen. Although it is synthetically produced, regulatory bodies such as FEMA (US) have approved its use in controlled quantities for enhancing sensory profiles in various consumables.
What regulatory standards govern the use of 4-methyl biphenyl, and how is it sourced?
4-methyl biphenyl is evaluated and regulated under FEMA (US) guidelines, where it is assigned number 3186 and generally recognized as safe for flavoring at specified levels. Additionally, JECFA and EFSA (EU) have conducted safety assessments supporting its use within established concentrations. The compound is typically synthesized chemically rather than extracted from natural sources. Safety data indicate no significant hazards under normal use, and recommended maximum usage levels are published by regulatory entities.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 1-methyl-4-phenylbenzene | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 644-08-6 |
| Pubchem (cid): | 12566 |
| Pubchem (sid): | 134976595 |
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 |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB32610 |
| FooDB: | FDB010551 |
| Export Tariff Code: | 2902.90.00.90 |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | 4-methyl biphenyl |
| Trivial Name | 4-Methylbiphenyl |
| Short Description | 4-methylbiphenyl |
| Formula | C13 H12 |
| CAS Number | 644-08-6 |
| FEMA Number | 3186 |
| ECHA Number | 211-409-0 |
| FDA UNII | 13J700766D |
| Nikkaji Number | J36.116J |
| Beilstein Number | 1904468 |
| MDL | MFCD00008544 |
| COE Number | 2292 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1334 4-methylbiphenyl |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 644-08-6 ; 4-METHYLBIPHENYL |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
| Penta International | Santa Cruz Biotechnology |
| Sigma-Aldrich | Synerzine |
| TCI AMERICA | WholeChem |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.23864746094 |
| Melting Point | 49 to 50°C @ 760 mm Hg |
| Boiling Point | 267 to 268°C @ 760 mm Hg |
| Boiling Point | 134 to 136°C @ 15 mm Hg |
| Vapor Pressure | 0.013 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 4.63 |
| Solubility | |
| alcohol | Yes |
| water, 6.968 mg/L @ 25 °C (est) | Yes |
| water, 4.05 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| floral, spicy, wintergreen, anise, waxy, minty, tarragon, cooling | |
| General comment | At 1.00 % in dipropylene glycol. floral spicy wintergreen anise waxy mint |
| Mosciano, Gerard P&F 21, No. 3, 51, (1996) | Floral, spicy, wintergreen, estragole and waxy with cooling, minty nuances |
| Flavor Type: Spicy | |
| grape, fig, spicy, tarragon, fennel, floral, wintergreen | |
| General comment | Grape fig |
| Mosciano, Gerard P&F 21, No. 3, 51, (1996) | At 12.00 ppm. Spicy, estragole, fennel, floral and wintergreen |
Potential Uses
| Applications | |
| Flavoring purposes | Chocolate , Herbal , Licorice , Mint , Wintergreen |
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: | |
| oral-rat LD50 2570 mg/kg Food and Cosmetics Toxicology. Vol. 13, Pg. 487, 1975. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 4-methyl biphenyl usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.0085 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.08 (μg/capita/day) | ||
| Threshold of Concern: | 90 (μg/person/day) | ||
| Structure Class: | III | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 4 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 5.00000 | |
| fruit ices: | - | 5.00000 | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the Panel on Food Additives,Flavourings, Processing Aids and Materials in Contact with Food (AFC) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):644-08-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :12566 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 1-methyl-4-phenylbenzene |
| Chemidplus:0000644086 |
| RTECS:DV5460000 for cas# 644-08-6 |