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2,5-xylenol
2,5-xylenol is a dimethyl-substituted phenol used as a flavor and fragrance agent with a phenolic, smoky odor.
General Material Description
2,5-xylenol, also known under trivial synonyms such as 2,5-dimethylphenol or p-xylenol, is an aromatic organic compound featuring a phenolic structure with two methyl groups positioned at the 2 and 5 locations of the benzene ring. It appears as a colorless to pale yellow liquid or solid with a characteristic phenolic odor. The molecular formula is C8H10O, and it has a molecular weight of approximately 122.17 g/mol. It exhibits sensory notes described as sweet naphthyl, phenolic, smoky, and bacon-like, contributing to its utility in flavor and fragrance formulations. This compound is commercially available either by extraction or synthetic preparation and is documented in controlled-vocabulary chemical databases such as PubChem. Its application extends primarily to aroma composition and flavor enhancement in food and cosmetic products.
Occurrence, Applicability & Potential Uses
2,5-xylenol occurs naturally in Arabica coffee beans and is identified as a component in whiskey aromas, contributing phenolic and smoky notes. Its use as a flavoring agent targets bacon and smoke flavor profiles due to its characteristic odor. In cosmetic goods, it serves as a perfuming agent, imparting distinctive scent qualities. Regulatory frameworks such as FEMA (US) provide guidelines on its safe application levels in foods and flavors. The compound's inclusion in the IFRA (Global) Code of Practice ensures safety compliance in fragrances. Its specific sensory properties enable utilization in complex blends requiring phenolic aroma characteristics.
Physico-Chemical Properties Summary
2,5-xylenol possesses moderate volatility with a boiling point range of 211 to 212 °C at standard atmospheric pressure, and a melting point between 75 and 77 °C. It has a specific gravity near 0.971 at 25 °C, indicating a density slightly less than water. The compound’s vapor pressure at room temperature (25 °C) is low, approximately 0.128 mmHg, indicating limited volatility in normal conditions. It exhibits a Log P (octanol-water partition coefficient) of about 2.33, suggesting moderate lipophilicity. Solubility assessments reveal it dissolves in alcohols and shows limited but measurable aqueous solubility (~3500 mg/L at 25 °C). These physicochemical traits affect its behavior in formulations, influencing volatility, solubility, and dispersion within aromatic mixtures.
FAQ
What is 2,5-xylenol and what are its primary characteristics?
2,5-xylenol is an aromatic compound classified as a dimethylphenol, characterized by two methyl groups attached to a phenol ring. It has a molecular weight of approximately 122.17 g/mol and a chemical formula of C8H10O. The compound is recognized for its phenolic, smoky, and bacon-like odor notes. It appears as a colorless or pale yellow substance and is used primarily as a flavor and fragrance ingredient. Multiple synonyms exist, including 2,5-dimethylphenol and p-xylenol, reflecting its structural nomenclature.
Where does 2,5-xylenol occur naturally and how is it used in industry?
This compound naturally occurs in sources such as Arabica coffee beans and whiskey, where it contributes distinct phenolic and smoky aroma facets. Industrially, it is applied as a flavoring agent for food products to impart bacon and smoke flavor notes. It also serves as a perfuming agent in cosmetic formulations. Its usage is governed by standards including FEMA (US) and IFRA (Global), ensuring application within safe exposure limits. The compound’s physicochemical properties determine its suitability in various aromatic blends.
What safety and regulatory considerations apply to 2,5-xylenol?
2,5-xylenol's use in flavors and fragrances is regulated by agencies such as FEMA (US) and IFRA (Global), which set guidelines for maximum usage levels to ensure consumer safety. Toxicity data indicate oral LD50 values in rodents range around hundreds of mg/kg, highlighting the need for controlled exposure. It is classified as toxic (T) and dangerous for the environment (N) under European chemical regulations and requires appropriate handling. Safety data sheets recommend avoiding skin contact and environmental release. Comprehensive evaluations by European Food Safety Authority (EFSA) and JECFA provide scientific assessments supporting its regulated use.
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
| 2,5-dimethylphenol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 95-87-4 |
| Pubchem (cid): | 7267 |
| Pubchem (sid): | 134972199 |
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): | HMDB30540 |
| FooDB: | FDB002413 |
| Export Tariff Code: | 2907.19.6100 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Formulations/Preparations: •xylenol 100; a high purity fraction of 2,4- and 2,5- xylenol (ortho xylenols); typical composition: 2,4- and 2,5-xylenol 93%; meta para cresol 2%; other xylenols 5%. from table •pitt-consol xylenol 410 is a synthetic xylenol blend homolog distribution, wt %: 2,6-xylenol, 1; 2,4-xylenol, 42; 2,5-xylenol, 43; 2,3-xylenol group, 14. xylenol 410 | |
General Material Information
| Preferred name | 2,5-xylenol |
| Trivial Name | 2,5-Dimethylphenol |
| Short Description | 2,5-dimethylphenol |
| Formula | C8 H10 O |
| CAS Number | 95-87-4 |
| FEMA Number | 3595 |
| Flavis Number | 4.019 |
| ECHA Number | 202-461-5 |
| FDA UNII | XH3E3564KX |
| Nikkaji Number | J43.459K |
| Beilstein Number | 1099260 |
| MDL | MFCD00002237 |
| COE Number | 537 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 706 2,5-xylenol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 95-87-4 ; 2,5-XYLENOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 122.16690063477 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Melting Point | 75 to 77°C @ 760 mm Hg |
| Boiling Point | 211 to 212°C @ 760 mm Hg |
| Vapor Pressure | 0.128 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.33 |
| Solubility | |
| alcohol | Yes |
| water, 3835 mg/L @ 25 °C (est) | Yes |
| water, 3540 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Phenolic | |
| sweet, naphthyl, phenolic, smoky, bacon | |
| General comment | At 0.10 % in propylene glycol. sweet naphthyl phenolic smoke bacon |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | Sweet, naphthyl, phenolic, smoke, bacon and Iysol-like |
| Flavor Type: Musty | |
| musty, chemical, stringent, phenolic | |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | At 10.00 ppm. Musty, chemical, stringent and phenolic |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Bacon , Smoke |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| T N - Toxic, Dangerous for the environment. | |
| R 24/25 - Toxic in contact with skin and if swallowed. R 34 - Causes burns. R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. S 01/02 - Keep locked up and 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 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately. 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: | |
| oral-rat LD50 444 mg/kg (Maazik, 1968) oral-rabbit LD50 938 mg/kg (Maazik, 1968) oral-mouse LD50 383 mg/kg (Maazik, 1968) gavage-rat LD50 (De Cresente, 1982) oral-mouse LD50 383 mg/kg BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968. oral-rabbit LD50 938 mg/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: ATAXIA Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968. oral-rat LD50 444 mg/kg Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972. unreported-rat LD50 730 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 227, 1935. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.49 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.03 (μg/capita/day) | ||
| 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: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 4.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 2.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | 2.00000 | |
| jams / jellies: | - | - | |
| meat products: | - | 2.00000 | |
| milk products: | - | - | |
| nut products: | - | 2.00000 | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | 2.00000 | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 2.00000 | |
| 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): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25 View page or View pdf |
| Safety and efficacy of eight compounds belonging to different chemical groups when used as flavourings for cats and dogs View page or View pdf |
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):95-87-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7267 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2261 |
| WGK Germany:3 |
| 2,5-dimethylphenol |
| Chemidplus:0000095874 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:ZE5775000 for cas# 95-87-4 |