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para-dimethyl hydroquinone

Chemical Structure

General Material Information

Preferred name para-dimethyl hydroquinone
Trivial Name 1,4-Dimethoxybenzene
Short Description p-dimethoxybenzene
Formula C8 H10 O2
CAS Number 150-78-7
FEMA Number 2386
Flavis Number 4.034
ECHA Number 205-771-9
FDA UNII 24WC6T6X0G
Nikkaji Number J5.858K
Beilstein Number 0774605
MDL MFCD00008401
COE Number 2059
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1250 p-dimethoxybenzene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 150-78-7 ; P-DIMETHOXYBENZENE
Synonyms
  • benzene, 1,4-dimethoxy-
  • di methyl hydroquinone
  • 1,4-dimethoxy benzene
  • 1,4-dimethoxy-benzene
  • 1,4-dimethoxybenzene
  • 4-dimethoxybenzene
  • p- dimethoxybenzene
  • para- dimethoxybenzene
  • 1,4-dimethoxybenzol
  • dimethyl ether hydroquinone
  • dimethyl hydroquinone
  • p- dimethyl hydroquinone
  • dimethyl hydroquinone ether
  • dimethylhydroquinone
  • p- dimethylhydroquinone
  • hydroquinone dimethyl ether
  • hydrquinone dimethyl ether
  • p- methoxyanisole
  • para- methoxyanisole
  • methyl p-methoxyphenyl ether
  • methyl para-methoxyphenyl ether
  • quinol dimethyl ether
  • Benzene, p-dimethoxy-
  • 1,4-Dimethoxybenzene
  • p-Dimethoxybenzene
  • DMB
  • p-Methoxyanisole
  • 4-Methoxyanisole
  • 1,4-Dimethoxybenzol
  • p-Hydroquinone dimethyl ether
  • Methyl 4-methoxyphenyl ether
  • NSC 7483

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

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Literature & References

1,4-dimethoxybenzene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:150-78-7
Pubchem (cid):9016
Pubchem (sid):134973236
Pherobase:View
Publications by PubMed
Theoretic calculation for understanding the oxidation process of 1,4-dimethoxybenzene-based compounds as redox shuttles for overcharge protection of lithium ion batteries.
Intramolecular electronic couplings in class II/III organic mixed-valence systems of bis(1,4-dimethoxybenzene).
Ozonolysis of lignin models in aqueous solution: anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and 1,3,5-trimethoxybenzene.
Perception of floral volatiles involved in host-plant finding behaviour: comparison of a bee specialist and generalist.
Highly stable high performance liquid chromatography stationary phase based on direct chemical modification of organic bridges in hybrid silica.
1,4-Dimethoxybenzene, a floral scent compound in willows that attracts an oligolectic bee.
2-Chloro-1,4-dimethoxybenzene as a mediator of lignin peroxidase catalyzed oxidations.
2-Chloro-1,4-dimethoxybenzene cation radical: formation and role in the lignin peroxidase oxidation of anisyl alcohol.
Size-selected gold clusters on porous titania as the most "gold-efficient" heterogeneous catalysts.
2-chloro-1,4-dimethoxybenzene as a novel catalytic cofactor for oxidation of anisyl alcohol by lignin peroxidase.
The de novo production of drosophilin A (tetrachloro-4-methoxyphenol) and drosophilin A methyl ether (tetrachloro-1,4-dimethoxybenzene) by ligninolytic basidiomycetes.
[Antibacterial activity of secondary metabolites from Aspergillus awamori F12 isolated from rhizospheric soil of Rhizophora stylosa Griff].
Aerobic oxidative coupling of arenes and olefins through a biomimetic approach.
Simultaneous determination of charge number and diffusion coefficient of 2-chloro-1,4-dimethoxybenzene in acetonitrile using potential-step chronoamperometry.
Reversible photochemically gated transformation of a hemicarcerand to a carcerand.
Degradation and transformation products of acetaminophen in soil.
Ecological relationship between floral thermogenesis and pollination in Nelumbo lutea (Nelumbonaceae).
Hydrogen-bonded inclusion compounds with reversed polarity: anionic metal-complexes and cationic organic linkers.
Quantitative preparative gas chromatography of caffeine with nuclear magnetic resonance spectroscopy.
Halogen-substituted (C-β-D-glucopyranosyl)-hydroquinone regioisomers: synthesis, enzymatic evaluation and their binding to glycogen phosphorylase.
Synthesis and X-ray crystal structure of a difunctionalized pillar[5]arene at A1/B2 positions by in situ cyclization and deprotection.
Epimeric monosaccharide-quinone hybrids on gold electrodes toward the electrochemical probing of specific carbohydrate-protein recognitions.
Regioselectivity in the nitration of dialkoxybenzenes.
Transcriptional response of zebrafish embryos exposed to neurotoxic compounds reveals a muscle activity dependent hspb11 expression.
Pairwise substitution effects, inter- and intramolecular hydrogen bonds in methoxyphenols and dimethoxybenzenes. Thermochemistry, calorimetry, and first-principles calculations.
Nitration of veratryl alcohol by lignin peroxidase and tetranitromethane.
Oxidation of dimethoxylated aromatic compounds by lignin peroxidase from Phanerochaete chrysosporium.
Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate.
Crystallographic, kinetic, and spectroscopic study of the first ligninolytic peroxidase presenting a catalytic tyrosine.
Guest-induced assembly of tetracarboxyl-cavitand and tetra(3-pyridyl)-cavitand into a heterodimeric capsule via hydrogen bonds and CH-halogen and/or CH-pi interaction: control of the orientation of the encapsulated guest.
Escherichia coli expression and in vitro activation of a unique ligninolytic peroxidase that has a catalytic tyrosine residue.
Analysis of biogenic volatile organic compounds in zucchini flowers: identification of scent sources.
Reactions within p-difluorobenzene/methanol heterocluster ions: a detailed experimental and theoretical investigation.
Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium.
Application of microscale-preparative multidimensional gas chromatography with nuclear magnetic resonance spectroscopy for identification of pure methylnaphthalenes from crude oils.
Degradation of various alkyl ethers by alkyl ether-degrading Actinobacteria isolated from activated sludge of a mixed wastewater treatment.
Induction of forestomach lesions by butylhydroxyanisole and structurally related substances.
Inter- and intraspecific variation in floral scent in the genus salix and its implication for pollination.
para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.
Photoarylation/alkylation of bromonaphthols.
Variability in floral scent in rewarding and deceptive orchids: the signature of pollinator-imposed selection?
Photosensitized oxidation of sulfides: discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen.
Anodic oxidation of mono- and disubstituted 1,4-dimethoxybenzenes.
One-pot synthesis of C-glycosylic compounds (C-glycosides) from D-glucal, p-tolylsulfenyl chloride and aromatic/heteroaromatic compounds in the presence of Lewis acids.
Photochemistry of methoxyhydroquinone and methoxy-p-benzoquinone in solution related to the photoyellowing of the lignocellulosics.
Cis-Trans Isomerization and Oxidation of Radical Cations of Stilbene Derivatives.
Rate parameter changes by added albumin in the microsomal oxidative demethylation of deuteriated and non-deuteriated 4-methoxyanisole.
[Quantitative analysis of tripchlorolide in pharmaceutical preparation by RP-HPLC].
Mechanism of antitumoral activity of catechols in culture.
The ligninase of Phanerochaete chrysosporium generates cation radicals from methoxybenzenes.
Synthesis of new phytogrowth-inhibitory substituted aryl-p-benzoquinones.
Selective monoiodination of aromatic compounds with electrochemically generated I+ using micromixing.
Microbial anaerobic demethylation and dechlorination of chlorinated hydroquinone metabolites synthesized by basidiomycete fungi.
First synthesis of a polysaccharide-supported lignin model compound and study of its oxidation promoted by lignin peroxidase.
Role of face-to-face and edge-to-face aromatic interactions in the inclusion complexation of cyclobis(paraquat-p-phenylene): a theoretical study.
[Studies on the chemical constituents of chloroform extract of Dracaena cochinchinensis].
Facile oxidation of fused 1,4-dimethoxybenzenes to 1,4-quinones using NBS: fine-tuned control over bromination and oxidation reactions.
Volatile methoxybenzene compounds in grains with off-odors.
Effects of BHA and related phenols on the forestomach of rats.
Decrease in glucose oxidation in isolated brown fat cells from rats due to tropolone and dimethoxybenzene.
Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes: laser flash photolysis and product studies.
Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions.
Characterization of a novel manganese peroxidase-lignin peroxidase hybrid isozyme produced by Bjerkandera species strain BOS55 in the absence of manganese.
On the mechanism of inhibition of the veratryl alcohol oxidase activity of lignin peroxidase H2 by EDTA.
Are free radicals involved in tumor promotion?
Metallocyclic receptors with Re(I)/Os(II)-based moieties: molecular photophysics and selective molecular sensing.
Iodide as the mediator for the reductive reactions of peroxidases.
Transformation of chlorinated phenolic compounds in the genusRhodococcus.
Protective effects of butylated hydroxyanisole and its analogs on the lung toxicity of butylated hydroxytoluene in mice.
Inhibition by 2(3)-tert-butyl-4-hydroxyanisole and other antioxidants of epidermal ornithine decarboxylase activity induced by 12-O-tetradecanoylphorbol-13-acetate.

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):HMDB29671
FooDB:FDB000855
Export Tariff Code:2909.30.6000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 138.16610717773
Melting Point 56 to 60°C @ 760 mm Hg
Boiling Point 210 to 213°C @ 760 mm Hg
Vapor Pressure 0.25 mmHg @ 25 °C
Vapor Density 4.8
Flash Point TCC Value 100 °C TCC
logP (o/w) 2.04
Shelf life 36 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 1543 mg/L @ 25 °C (est) Yes
water No
Stability
non-discoloring in most media Unspecified

Organoleptic Properties

Odor Type: Green
sweet, green, hay new mown hay, fennel
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity 76 hour(s) at 100.00 %
Luebke, William tgsc, (1981) At 1.00 % in dipropylene glycol. sweet green new mown hay fennel
Flavor Type: Green
green, hawthorn, hay new mown hay, anisic, anise, fennel, powdery, fatty
Luebke, William tgsc, (1981) Sweet green hawthorn new mown hay anisic anise fennel powdery fatty
General comment Aromatic, dusty, earthy

Occurrences

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 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)
Skin irritation (Category 2), H315
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H315 - Causes skin irritation
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P271 - Use only outdoors or in a well-ventilated area.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 3600 mg/kg
(Moreno, 1973ae)

oral-rat LD50 8500 mg/kg
(Moreno, 1973ae)

oral-mouse LD50 4000 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 4(2), Pg. 30, 1960.

intraperitoneal-mouse LD50 100 mg/kg
National Technical Information Service. Vol. AD277-689

oral-rat LD50 3600 mg/kg
Food and Cosmetics Toxicology. Vol. 16, Pg. 715, 1978.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 16, Pg. 715, 1978.

Inhalation Toxicity:
inhalation-rat LC50 500 mg/24hours
Food and Cosmetics Toxicology. Vol. 16, Pg. 715, 1978.

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 para-dimethyl hydroquinone usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 15.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 7.00 (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: -5.80000
beverages(nonalcoholic): -8.10000
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: -4.70000
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
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):150-78-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9016
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
1,4-dimethoxybenzene
Chemidplus:0000150787
EPA/NOAA CAMEO:hazardous materials
RTECS:150-78-7