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meta-eugenol
Meta-eugenol is a natural aromatic phenol with a spicy, carnation odor, occurring in betel and used in natural extractives.
General Material Description
Meta-eugenol, also known as chavibetol or 5-allyl-2-methoxyphenol, is a naturally occurring phenolic compound characterized by its spicy, carnation-like aroma. It has the molecular formula C10H12O2 and a molecular weight of approximately 164.2 g/mol. The compound appears as a colorless to pale yellow liquid under standard conditions. A key member of the phenylpropanoid class, meta-eugenol features a methoxy group and an allylic side chain on the aromatic ring. Its sensory attributes make it notable in flavor and fragrance research. Meta-eugenol is found primarily in plant sources such as betel leaves and Haplophyllum myrtifolium, from which it can be extracted as a natural substance. Its chemical identity and properties are well documented in public chemical databases including PubChem. This compound’s natural origin and distinctive odor profile underline its relevance in the study of aromatic compounds and natural extractives.
Occurrence, Applicability & Potential Uses
Meta-eugenol is naturally present in several plants, notably in the betel leaf (Piper betle) and Haplophyllum myrtifolium. These botanical sources contribute to its extraction for use in natural substances and extractives, where its spicy odor profile is valued. The compound's inclusion in natural formulations is governed by regulations such as REACH (EU), which oversee its application and safety in industrial contexts. Meta-eugenol's spicy carnation scent is harnessed for olfactory purposes in fragrance applications; however, its specific usage levels are restricted in some frameworks due to limited toxicological data. While it shows potential in flavors and fragrances, guidance typically recommends caution or non-use for flavor formulation. As a natural aromatic phenol, meta-eugenol finds niche applicability in perfumery and related industries focusing on natural extractives.
Physico-Chemical Properties Summary
Meta-eugenol displays several physical and chemical properties relevant to its handling and formulation. It is a liquid with a specific gravity of 1.0646 at 25 °C, indicating a density slightly higher than water. The compound melts between 8 and 9 °C and boils at 254 to 255 °C at standard atmospheric pressure, reflecting moderate volatility. Its vapor pressure at 25 °C measures approximately 0.011 mmHg, consistent with low volatility typical for phenolic ethers. The estimated octanol-water partition coefficient (log P) is about 2.204, suggesting moderate hydrophobicity, which influences solubility and bioavailability in formulations. Meta-eugenol is soluble in alcohol and has limited water solubility at around 305 mg/L at 25 °C, with conflicting data about water solubility requiring attention in processing. It has a flash point of 252 °F (approximately 122 °C), indicating relative safety from ignition at room temperature under typical conditions. These properties inform proper storage, extraction, and formulation strategies in natural product applications.
FAQ
What is meta-eugenol and where is it found?
Meta-eugenol, also known as chavibetol, is a naturally occurring aromatic phenol characterized by a spicy and carnation-like odor. It is found in various plants including betel leaves (Piper betle) and Haplophyllum myrtifolium. The compound consists of a methoxy group and an allyl side chain attached to a phenol ring, giving it distinctive sensory and chemical characteristics.
How is meta-eugenol used and what are its main applications?
Meta-eugenol is primarily used as a natural substance and extractive owing to its characteristic spicy aroma. Its applications focus on fragrance purposes where it contributes to compositions needing spicy or carnation-like notes. Despite its aromatic properties, usage in flavorings is generally not recommended due to regulatory guidance. The compound is extracted from botanical sources for selective use in perfumery and related industries.
What regulatory standards apply to meta-eugenol and how is it sourced?
Meta-eugenol is subject to chemical regulations such as REACH (EU), which provide frameworks for its registration and safe use. It occurs naturally in specific plants like betel and Haplophyllum myrtifolium, from which it is sourced as a natural extractive. Current guidelines recommend restricted or no use in flavoring applications, and safety assessments have recorded no significant hazard classifications under OSHA HCS (29 CFR 1910). Proper sourcing from verified plant materials ensures quality and compliance.
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | meta-eugenol |
| Trivial Name | Chavibetol |
| Short Description | chavibetol |
| Formula | C10 H12 O2 |
| CAS Number | 501-19-9 |
| FDA UNII | OE7NQ16G4D |
| Nikkaji Number | J6.118B |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 164.20404052734 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Melting Point | 8 to 9°C @ 760 mm Hg |
| Boiling Point | 254 to 255°C @ 760 mm Hg |
| Boiling Point | 127 to 128°C @ 10 mm Hg |
| Vapor Pressure | 0.011 mmHg @ 25 °C |
| Flash Point TCC Value | 122.4 °C TCC |
| logP (o/w) | 2.204 est |
| Solubility | |
| alcohol | Yes |
| water, 304.7 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Spicy | |
| spicy, carnation | |
| General comment | At 100.00 %. spicy carnation |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Betel |
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 meta-eugenol usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for meta-eugenol 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 :596375 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| 2-methoxy-5-prop-2-enylphenol |
| Chemidplus:0000501199 |