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4-ethoxyphenol
4-ethoxyphenol is a phenol derivative used primarily for its antioxidant effects and found in star anise oil with distinct fruity and phenolic notes.
General Material Description
4-ethoxyphenol is a phenolic compound with the molecular formula C8H10O2, known by synonyms such as p-ethoxyphenol and hydroquinone monoethyl ether. This colorless to pale liquid displays characteristic aromatic features associated with phenolic ethers, including mild fruity, cherry, and medicinal notes, often described as phenolic and nutty. Structurally, it consists of a hydroxy group para-substituted with an ethoxy group on a benzene ring. Referenced in the PubChem database, it is naturally present in essential oils such as star anise. It has been sourced industrially via synthetic routes but also occurs as a minor constituent in various botanical extracts. This compound's chemical characteristics contribute to its applications as an antioxidant and a flavoring-related agent in certain specialized uses.
Occurrence, Applicability & Potential Uses
4-ethoxyphenol naturally occurs in star anise oil, contributing to its aromatic profile. Its phenolic structure imparts antioxidant properties utilized in essential oils and food contact materials, notably sealing gaskets for food containers. Regulatory bodies such as FEMA (US) categorize it under flavoring substances, assigning it a FEMA number 3695 and evaluating its safety for specific uses. The compound is applied to enhance product stability by preventing oxidative degradation. Despite historical cosmetic applications, its use in fragrances is prohibited due to safety concerns regulated by IFRA (Global), which restricts its application stemming from effects such as depigmentation. In food technology, usage levels are controlled and monitored, with provisions established to minimize consumer exposure while harnessing its functional benefits.
Physico-Chemical Properties Summary
4-ethoxyphenol exhibits a melting point ranging from 64 to 67°C and a boiling point near 246 to 247°C at standard atmospheric pressure, indicating solid state near ambient temperature and moderate volatility. Its vapor pressure at 25°C is low, about 0.017 mmHg, reflecting limited evaporation under room conditions. The compound possesses a logP value of approximately 1.81, suggesting moderate lipophilicity which affects its solubility profile and partitioning behavior. It dissolves readily in alcohols, dipropylene glycol, and propylene glycol, but shows minimal water solubility estimated at 9222 mg/L at 25°C. These properties influence its incorporation into formulations, favoring compatibility with organic solvents and oils. The flash point measured at 255°F (approximately 124°C) confirms its relative thermal stability prior to ignition. Collectively, these parameters guide its handling, storage, and application in industrial settings.
FAQ
What is 4-ethoxyphenol and what are its main characteristics?
4-ethoxyphenol is a phenolic ether compound with the molecular formula C8H10O2. It is known for its antioxidant properties and presence in natural essential oils such as star anise oil. The substance has a mild fruity and phenolic aroma with cherry and medicinal notes. It is often referenced by synonyms including p-ethoxyphenol and hydroquinone monoethyl ether. The compound appears as a pale solid near room temperature and is chemically characterized by a hydroxy group para-substituted with an ethoxy group on a benzene ring.
Where does 4-ethoxyphenol occur naturally, and how is it utilized industrially?
4-ethoxyphenol occurs naturally in star anise essential oil, contributing to its characteristic aroma. Industrially, it is used primarily as an antioxidant within essential oils and in food contact materials such as sealing gaskets for food containers, helping to prevent oxidation and degradation. Its application in fragrances has been discontinued due to regulatory restrictions. The compound also serves as a flavoring-related agent under strict usage limits defined by regulatory authorities.
What regulatory standards apply to 4-ethoxyphenol and how is its safety managed?
Regulatory oversight for 4-ethoxyphenol includes evaluations by FEMA (US) where it is assigned FEMA number 3695 and classified in flavoring substance assessments. IFRA (Global) standards prohibit its use as a fragrance ingredient due to critical effects such as depigmentation. The European Food Safety Authority (EFSA) has conducted detailed assessments within flavoring group evaluations, ensuring usage levels in food-related applications comply with safety guidelines. Usage in food contact materials is regulated by FDA and other authorities to control exposure. Safety data indicate it is an irritant to eyes, skin, and respiratory system, necessitating appropriate handling precautions.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
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 |
| FDA Indirect Additives used in Food Contact Substances: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB32036 |
| FooDB: | FDB008737 |
| Export Tariff Code: | 2927.00.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 4-ethoxyphenol |
| Trivial Name | 4-Ethoxyphenol |
| Short Description | p-ethoxyphenol |
| Formula | C8 H10 O2 |
| CAS Number | 622-62-8 |
| FEMA Number | 3695 |
| Flavis Number | 4.037 |
| ECHA Number | 210-748-1 |
| FDA UNII | 605352N8AQ |
| Nikkaji Number | J45.017K |
| Beilstein Number | 1907114 |
| MDL | MFCD00002334 |
| COE Number | 2258 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 720 hydroquinone monoethyl ether |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 622-62-8 ; HYDROQUINONE MONOETHYL ETHER |
| Synonyms |
|
Suppliers
| BOC Sciences | ExtraSynthese |
| Parchem | Penta International |
| Sigma-Aldrich: Aldrich | Synerzine |
| TCI AMERICA | Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.16610717773 |
| Melting Point | 64 to 67°C @ 760 mm Hg |
| Boiling Point | 246 to 247°C @ 760 mm Hg |
| Vapor Pressure | 0.017 mmHg @ 25 °C |
| Flash Point TCC Value | 123.89 °C TCC |
| logP (o/w) | 1.81 |
| Solubility | |
| alcohol | Yes |
| dipropylene glycol | Yes |
| propylene glycol | Yes |
| water, 9222 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Animal | |
| hawthorn, phenolic, plastic, nutty | |
| Odor strength | low , recommend smelling in a 10.00 % solution or less |
| Substantivity | 141 hour(s) at 10.00 % in dipropylene glycol |
| Luebke, William tgsc, (2007) | At 10.00 % in dipropylene glycol. mild hawthorn phenolic plastic nutty |
| Flavor Type: Fruity | |
| fruity, cherry, cherry maraschino cherry, medicinal, nutty, phenolic | |
| Luebke, William tgsc, (2007) | Fruity cherry maraschino cherry medicinal nutty phenolic |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Other purposes | Antioxidant in essential oils |
| Cosmetic purposes | Not used anymore |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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. | |
| 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: | |
| intraperitoneal-mouse LDLo 250 mg/kg Revue Belge de Pathologie et de Medecine Experimentale. Vol. 22, Pg. 1, 1952. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| food contact closures with sealing gaskets for food containers | |||
| IFRA Critical Effect: | |||
| Depigmentation | |||
| View the IFRA Standard | |||
| Recommendation for 4-ethoxyphenol usage levels up to: | |||
| PROHIBITED: Should not be used as a fragrance ingredient. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.37 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.40 (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 5.00000 | |
| 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: | - | - | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.50000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | 5.00000 | |
| 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): |
| 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 |
| 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 |
| Scientific Opinion on Flavouring Group Evaluation 96 (FGE.96): Consideration of 88 flavouring substances considered by EFSA for which EU production volumes / anticipated production volumes have been submitted on request by DG SANCO. Addendum to FGE. 51, 52, 53, 54, 56, 58, 61, 62, 63, 64, 68, 69, 70, 71, 73, 76, 77, 79, 80, 83, 84, 85 and 87. View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):622-62-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :12150 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 4-ethoxyphenol |
| Chemidplus:0000622628 |
| RTECS:SL3790000 for cas# 622-62-8 |