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meta-dimethyl hydroquinone

Meta-dimethyl hydroquinone, also called 1,3-dimethoxybenzene, is an aromatic compound used in flavor and fragrance applications, possessing a medicinal, root beer-like odor and chemical flavor notes.
Chemical Structure

General Material Description

Meta-dimethyl hydroquinone, commonly referenced by its preferred chemical name 1,3-dimethoxybenzene, is a volatile aromatic ether with the molecular formula C8H10O2. It appears as a clear liquid characterized by medicinal and root beer-like odor notes and exhibits a chemical flavor profile with spice and cooling qualities. This compound is also known under various synonyms, including m-dimethoxybenzene, dimethyl resorcinol, and meta-dimethyl hydroquinone, among others. It finds relevance in the flavor and fragrance industry as a key agent contributing to complex aroma profiles. The controlled vocabulary link for this compound is available on PubChem. It can be sourced through both synthetic methods and occurs naturally in several foodstuffs such as coffee, brandy, and certain cheeses.

Occurrence, Applicability & Potential Uses

Meta-dimethyl hydroquinone naturally occurs in various biological matrices, including brandy, coffee, butter, blue and gruyere cheese, kiwi fruit, rice, and in red mangrove bark oil from Cuba. Its presence contributes to the characteristic aromas of these materials. This compound is widely applied as a flavoring and fragrance agent in industrial formulations. Flavor enhancement uses often target brandy and cheese notes to reproduce or intensify complex sensory impressions. Regulatory evaluations under FEMA (US) classify it with FEMA number 2385, supporting its use in consumer products within defined concentration limits. Additionally, the International Fragrance Association (IFRA) regulates its use for perfuming agents, with guidance allowing concentrations up to 1.0% in fragrance concentrates to ensure safe application.

Physico-Chemical Properties Summary

Meta-dimethyl hydroquinone exhibits moderate volatility with a vapor pressure of 0.528 mmHg at 25°C, influencing its evaporation rate in applications. It has a melting point range of -55 to -52°C and boils between 215 and 217.5°C at atmospheric pressure, indicating thermal stability suitable for flavor and fragrance formulations. Its specific gravity ranges from 1.0661 to 1.07 at 25°C, and the refractive index is between 1.523 and 1.527 at 20°C, aiding in identification and purity assessment. The compound is slightly soluble in water, with an estimated solubility of 1105 mg/L at 25°C, but shows good solubility in alcohol, enabling use in various solvent systems. The logP value of 2.21 reflects moderate lipophilicity, affecting its partitioning behavior and interaction within mixtures. The flash point is approximately 86.7°C (186°F), implying relative safety in handling under standard conditions.

FAQ

What is meta-dimethyl hydroquinone and what are its key characteristics?
Meta-dimethyl hydroquinone is an aromatic ether chemically known as 1,3-dimethoxybenzene with the formula C8H10O2. It is a clear liquid noted for its medicinal, root beer-like odor and chemical flavor profile with spice and cooling notes. It has multiple synonyms and is utilized mainly as a flavor and fragrance agent due to these distinctive sensory properties.
Where does meta-dimethyl hydroquinone occur naturally and how is it applied?
This compound naturally appears in foods and beverages such as brandy, coffee, certain cheeses including blue and gruyere, butter, kiwi, and rice, as well as in red mangrove bark oil. It is primarily applied in flavoring formulations to enhance brandy and cheese notes and in fragrance products for its perfuming qualities. Regulatory guidance, such as IFRA standards, supports its use within safe concentration limits.
What regulations and safety assessments apply to meta-dimethyl hydroquinone for flavor and fragrance use?
Meta-dimethyl hydroquinone is recognized under FEMA (US) with number 2385 and assessed by agencies including JECFA. The IFRA Code of Practice (Global) advises limiting its concentration to a maximum of 1% in fragrance concentrates. Safety data classify it as an irritant under European directives, and exposure limits have been established based on toxicological studies. Comprehensive evaluations by EFSA and other bodies inform guidelines to ensure safe consumer use.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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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):HMDB29672
FooDB:FDB000856
Export Tariff Code:2909.30.6000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View

General Material Information

Preferred name meta-dimethyl hydroquinone
Trivial Name 1,3-Dimethoxybenzene
Short Description m-dimethoxybenzene
Formula C8 H10 O2
CAS Number 151-10-0
Deleted CAS Number 2104659-85-8
FEMA Number 2385
Flavis Number 4.016
ECHA Number 205-783-4
FDA UNII 2694Z07HQY
Nikkaji Number J5.861K
Beilstein Number 0878582
MDL MFCD00008384
COE Number 189
NMR Predictor External link
JECFA Food Flavoring 1249 m-dimethoxybenzene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 151-10-0 ; M-DIMETHOXYBENZENE
Synonyms
  • benzene, 1,3-dimethoxy-
  • benzene, m-dimethoxy-
  • benzene,3-dimethoxy-
  • 1,3-dimethoxy benzene
  • 1,3-dimethoxy-benzene
  • 1,3-dimethoxybenzene
  • m- dimethoxybenzene
  • meta- dimethoxybenzene
  • 1,3-dimethoxybenzol
  • meta- dimethyl hydroquinone
  • dimethyl resorcinol
  • dimethyl resourcinol
  • m- dimethylhydroquinone
  • dimethylresorcinol
  • 3-methoxyanisole
  • resorcinol dimethyl ether
  • 1,3-Dimethoxybenzene
  • m-Dimethoxybenzene
  • 3-Methoxyanisole
  • m-Methoxyanisole
  • NSC 8699
  • 3-Methoxyphenyl methyl ether
  • 2,4-Dimethoxybenzene

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 138.16610717773
Specific gravity @ 25 °C
Pounds per Gallon 8.871 to 8.903
Refractive Index 1.523 to 1.527 @ 20 °C
Melting Point -55 to -52°C @ 760 mm Hg
Boiling Point 85 to 87°C @ 7 mm Hg
Boiling Point 215 to 217.5°C @ 760 mm Hg
Vapor Pressure 0.528 mmHg @ 25 °C
Vapor Density 4.7
Flash Point TCC Value 85.56 °C TCC
logP (o/w) 2.21
Solubility
alcohol Yes
water, 1105 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Medicinal
acidic, fruity, nutmeg, neroli, sweet, cooling, medicinal, root beer
Odor strength medium , recommend smelling in a 1.00 % solution or less
Substantivity 64 hour(s) at 100.00 %
Luebke, William tgsc, (1998) At 1.00 % in dipropylene glycol. acid fruity nutmeg neroli
Mosciano, Gerard P&F 17, No. 3, 57, (1992) Sweet, cooling, medicinal, root beer-like
Flavor Type: Chemical
chemical, medicinal, spicy, cooling, root beer
Mosciano, Gerard P&F 17, No. 3, 57, (1992) Chemical, medicinal, spice, cooling root beer-like
General comment Chemical medicinal spice cooling root beer

Occurrences

Potential Uses

Applications
Odor purposes Anise , Coconut , Earth , Hazelnut , Neroli , Nutmeg , Root beer , Vanilla , Wintergreen
Flavoring purposes Brandy , Cheese
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
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:
oral-rat LD50 2500 mg/kg
(Moreno, 1978l)

oral-rat LD50 [sex: M,F] 2560 mg/kg
(Bär & Griepentrog, 1967)

intraperitoneal-mouse LD50 900 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA BEHAVIORAL: TREMOR
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 185, 1957.

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
Recommendation for meta-dimethyl hydroquinone usage levels up to:
1.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 4.60 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -8.00000
beverages(nonalcoholic): -3.00000
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: --
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 23 (FGE.23): Aliphatic, alicyclic and aromatic ethers including anisole derivatives From chemical groups 15, 16 and 26 (Commission Regulation (EC) No 1565/2000 of 18 July 2000
View page or View pdf

Flavouring Group Evaluation 59 (FGE.59): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 (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 23, Revision 1 (FGE.23Rev1): Aliphatic, alicyclic and aromatic ethers including anisole derivatives from chemical groups 15, 16, 26 and 30[1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 59, Revision 1 (FGE.59Rev1): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting and 63rd meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 Rev2 (2010)
View page or View pdf

Scientific Opinion on the safety and efficacy of aromatic ethers including anisole derivatives (chemical group 26) when used as feed additives for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):151-10-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9025
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1,3-dimethoxybenzene
Chemidplus:0000151100
RTECS:CZ6474000 for cas# 151-10-0