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guaiacyl acetate

General Material Information

Preferred name	guaiacyl acetate
Trivial Name	Phenol, 2-methoxy-, 1-acetate
Short Description	2-methoxyphenyl acetate
Formula	C9 H10 O3
CAS Number	613-70-7
FEMA Number	3687
Flavis Number	9.174
ECHA Number	210-350-8
FDA UNII	K5YN7743HC
Nikkaji Number	J31.560E
MDL	MFCD00017221
COE Number	552
Bio Activity Summary	External link
NMR Predictor	External link
JECFA Food Flavoring	718 guaiacyl acetate
FDA Patent	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm	613-70-7 ; GUAIACYL ACETATE
Synonyms	acetic acid 2-methoxyphenyl ester 1-acetoxy-2-methoxybenzene 2-acetoxyanisole o- acetoxyanisole ortho- acetoxyanisole acetyl guaiacol o- acetyl guaiacol ortho- acetyl guaiacol o- anisyl acetate ortho- anisyl acetate eucol guaiacol acetate 2-methoxyphenol acetate 2-methoxyphenyl acetate o- methoxyphenyl acetate ortho- methoxyphenyl acetate (2-methoxyphenyl) acetate phenol, 2-methoxy-, acetate phenol, o-methoxy-, acetate (2-methoxyphenyl) acetate Phenol, 2-methoxy-, 1-acetate 1-Acetoxy-2-methoxybenzene o-Methoxyphenyl acetate o-Acetoxyanisole 2-Methoxyphenyl acetate o-Anisyl acetate O-Acetyl-2-methoxyphenol 2-Acetoxyanisole O-Acetylguaiacol NSC 3831

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

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Literature & References

	(2-methoxyphenyl) acetate
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	613-70-7
Pubchem (cid):	61155
Pubchem (sid):	135018159
Pherobase:	View

Publications by PubMed
Volatile fingerprint of Brazilian defective coffee seeds: corroboration of potential marker compounds and identification of new low quality indicators.
Aromatic profile of ciders by chemical quantitative, gas chromatography-olfactometry, and sensory analysis.
[Rapid identification 15 effective components of anti common cold medicine with MRM by LC-MS/MS].
Cooperative regulation of anxiety and panic-related defensive behaviors in the rat periaqueductal grey matter by 5-HT1A and μ-receptors.
Anxiolytic-like effect of lavender essential oil inhalation in mice: participation of serotonergic but not GABAA/benzodiazepine neurotransmission.
Enhancements of skin cell proliferations and migrations via 6-dehydrogingerdione.
Characterization of wood plastic composites made from landfill-derived plastic and sawdust: volatile compounds and olfactometric analysis.
Quantification and evaluation of kinetic bio-catalytic pathway of horseradish peroxidase in an electron mediated reaction system and its applications in plant extracts.
PEI-coated gold nanoparticles decorated with laccase: a new platform for direct electrochemistry of enzymes and biosensing applications.
In vitro degradation of lysine by ruminal fluid-based fermentations and by Fusobacterium necrophorum.
Immunolocalization of 8-5' and 8-8' linked structures of lignin in cell walls of Chamaecyparis obtusa using monoclonal antibodies.
Understanding changes in lignin of Panicum virgatum and Eucalyptus globulus as a function of ionic liquid pretreatment.
Evaluation of a potential starter culture for enhance quality of coffee fermentation.
Amperometric determination of total phenolic content in wine by laccase immobilized onto silver nanoparticles/zinc oxide nanoparticles modified gold electrode.
Depolymerization of oak wood lignin under mild conditions using the acidic ionic liquid 1-H-3-methylimidazolium chloride as both solvent and catalyst.
Comparative study of organosolv lignin extracted from prairie cordgrass, switchgrass and corn stover.
Development of an amperometric polyphenol biosensor based on fungal laccase immobilized on nitrocellulose membrane.
An amperometric biosensor based on laccase immobilized onto MnO2NPs/cMWCNT/PANI modified Au electrode.
Simultaneous determination of codeine, ephedrine, guaiphenesin and chlorpheniramine in beagle dog plasma using high performance liquid chromatography coupled with tandem mass spectrometric detection: application to a bioequivalence study.
Quality evaluation of olive oil by statistical analysis of multicomponent stable isotope dilution assay data of aroma active compounds.
Extraction of lignins from aqueous-ionic liquid mixtures by organic solvents.
Fabrication of polyphenol biosensor based on laccase immobilized on copper nanoparticles/chitosan/multiwalled carbon nanotubes/polyaniline-modified gold electrode.
Polyphenol biosensor based on laccase immobilized onto silver nanoparticles/multiwalled carbon nanotube/polyaniline gold electrode.
Phenol Glycosides with In Vitro anti-Helicobacter pylori Activity from Hypericum erectum Thunb.
Modulating the synthetase activity of penicillin G acylase in organic media by addition of N-methylimidazole: using vinyl acetate as activated acyl donor.
A hydrogel-based enzyme-loaded polymersome reactor.
Effects of foliar fertilization and arbuscular mycorrhizal colonization on Salvia officinalis L. growth, antioxidant capacity, and essential oil composition.
Fate of key odorants in Sauternes wines through aging.
A sensitive liquid chromatography-electrospray ionization-mass spectrometry method for the simultaneous determination of pentoxyverine citrate and guaifenesin in human plasma---application to pharmacokinetic and bioequivalence studies.
Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols.
Highly acylated (acetylated and/or p-coumaroylated) native lignins from diverse herbaceous plants.
Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine.
Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols.
Effect of essential oil active compounds on rumen microbial fermentation and nutrient flow in in vitro systems.
Phenolic constituents in the fruits of Cinnamomum zeylanicum and their antioxidant activity.
Theoretical prediction of the relationship between phenol function and COX-2/AP-1 inhibition for ferulic acid-related compounds.
Structure and function of the antennal sensilla of the palm weevil Rhynchophorus palmarum (Coleoptera, Curculionidae).
Simultaneous determination of some active ingredients in cough and cold preparations by gas chromatography, and method validation.
Use of ozone and/or UV in the treatment of effluents from board paper industry.
Inhibitory effect on activator protein-1, nuclear factor-kappaB, and cell transformation by extracts of strawberries (Fragaria x ananassa Duch.).
Perceptual interactions in odour mixtures: odour quality in binary mixtures of woody and fruity wine odorants.
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.
Anti-tumor-promoting activities of selected pungent phenolic substances present in ginger.
Purification of the precursor for the automated radiosynthesis of [18F]FCWAY by counter-current chromatography.
Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines.
Characterization of odor-active compounds in Californian chardonnay wines using GC-olfactometry and GC-mass spectrometry.
Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae).
Gateways to Clinical Trials. June 2002.
Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin.
Microbial enantioselective ester hydrolysis for the preparation of optically active 4,1-benzoxazepine-3-acetic acid derivatives as squalene synthase inhibitors.
Aromatase inhibitors from Broussonetia papyrifera.
Antioxidative and antitumor promoting effects of [6]-paradol and its homologs.
Synthesis of (+)-lariciresinol 3a-acetate, a lignan from Aglaia elaeagnoidea.
Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure.
Determination of 1-(2-methoxyphenyl)piperazine derivatives of isocyanates at low concentrations by temperature-programmed miniaturized liquid chromatography.
Diarylheptanoids suppress expression of leukocyte adhesion molecules on human vascular endothelial cells.
Biosynthesis, molecular structure, and domain architecture of potato suberin: a (13)C NMR study using isotopically labeled precursors.
Effects of the sniffing port air makeup in gas chromatography-olfactometry.
The mechanism of action of amtolmetin guacyl, a new gastroprotective nonsteroidal anti-inflammatory drug.
Anti-tumor promoting potential of naturally occurring diarylheptanoids structurally related to curcumin.
[Chemical constituents of the leaves of Ginkgo biloba].
[Substituted methoxyphenol with antioxidative activity: correlation between physicochemical and biological results].
Studies on the preparation of bioactive lignans by oxidative coupling reaction. III. Synthesis of polyphenolic benzofuran and coumestan derivatives by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate and their inhibitory effect on lipid peroxidation.
Immunostimulation of tiger shrimp (Penaeus monodon) hemocytes for generation of microbicidal substances: analysis of reactive oxygen species.
Development and validation of a high-performance liquid chromatographic method for the determination of methocarbamol in human plasma.
Enzymatic reduction of xenobiotic alpha,beta-unsaturated ketones: formation of allyl alcohol metabolites from shogaol and dehydroparadol.
Effects of glucocorticoids on 5-HT1A presynaptic function in the mouse.
[A bioequivalence study in man of tablet and capsule formulations of the nonsteroidal anti-inflammatory compound 2-methoxyphenyl 1-methyl-5-(p-methylbenzoylpyrrol)-2-acetamidoacetate].
[A bioequivalence study of tablet and powder formulations of the nonsteroidal anti-inflammatory drug 2-methoxyphenyl 1-methyl-5-(p-methylbenzoylpyrrol)-2-acetamidoacetate].
Studies to demonstrate inhibition of functional activity of neutrophil lysosomal enzymes with ANCA.
A liquid chromatographic assay using a high-speed column for the determination of lamotrigine, a new antiepileptic drug, in human plasma.
High-performance liquid chromatographic analysis of methocarbamol enantiomers in biological fluids.
The effects of corticosterone on 5-HT receptor function in rodents.
Design and evaluation of a solid sampler for the monitoring of airborne 1,6-hexamethylene diisocyanate (HDI) and its prepolymers in two-component spray painting.
Analysis of carbohydrate residues on human thyroid peroxidase (TPO) and thyroglobulin (Tg) and effects of deglycosylation, reduction and unfolding on autoantibody binding.
Degradation of synthetic lignins and some lignin monomers by the yeastRhodotorula glutinis.
[An application of electrochemical detector to dental pharmacology].
Biomimetic oxidation of nonphenolic lignin models by Mn(III): new observations on the oxidizability of guaiacyl and syringyl substructures.
Antioxidant properties of conjugated bilirubin and biliverdin: biologically relevant scavenging of hypochlorous acid.
Inhibition of peroxidase-catalyzed reactions by deferoxamine.
Radiochemical detection of dihydrodiol dehydrogenase: distribution of the enzyme in male Sprague-Dawley rat tissues and its sensitivity to inhibition by indomethacin and 6-medroxyprogesterone acetate.
Cytochrome c/H2O2-mediated one electron oxidation of carcinogenic N-fluorenylacetohydroxamic acids to nitroxyl free radicals.
Aromatic retinoic acid analogues. 2. Synthesis and pharmacological activity.
Constituents of essential oil of Aframomum giganteum.
[Experimental studies on the sealing properties of various kind of root canal sealers and pastes in vitro, with special reference to non-eugenol preparations (author's transl)].
[The alleged antagonism to vitamin E of phenolic esters, particulary of guaiacol acetate].
Publications by J-Stage
Microbial Enantioselective Ester Hydrolysis for the Preparation of Optically Active 4,1-Benzoxazepine-3-acetic Acid Derivatives as Squalene Synthase Inhibitors

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
Metabolomics Database:	Search
HMDB (The Human Metabolome Database):	HMDB32030
FooDB:	FDB008730
Export Tariff Code:	2918.99.4700
ChemSpider:	View

Suppliers

BOC Sciences	Fleurchem
Matrix Scientific	Penta International
Reincke & Fichtner	Santa Cruz Biotechnology
Sigma-Aldrich: Aldrich	Synerzine
TCI AMERICA	The John D. Walsh Company
Fleurchem, Inc.	Penta International Corporation
Synerzine, Inc.	The John D. Walsh Company, Inc

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	166.17630004883
Specific gravity	@ 20 °C
Pounds per Gallon	9.464 to 9.48
Refractive Index	1.513 to 1.515 @ 20 °C
Melting Point	31 to 32°C @ 760 mm Hg
Boiling Point	122 to 124°C @ 18 mm Hg
Boiling Point	239 to 241°C @ 760 mm Hg
Acid Value	1 max KOH/g
Vapor Pressure	0.042 mmHg @ 25 °C
Flash Point TCC Value	110 °C TCC
logP (o/w)	1.38
Shelf life	24 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, 4249 mg/L @ 25 °C (est)	Yes

Organoleptic Properties

Odor Type: Woody
sweet, woody, spicy, dry, clove, powdery, smoky, phenolic, guaiacol, ham, vanilla
Luebke, William tgsc, (1987)	At 100.00 %. sweet woody spice dry clove powdery smoky
Mosciano, Gerard P&F 23, No. 3, 55, (1998)	At 5.00 %. Phenolic, guaiacol, smoky and ham-like with a woody, vanilla nuance
Flavor Type: Woody
woody, guaiacol, smoky, astringent, phenolic, vanilla, coumarinic
Mosciano, Gerard P&F 23, No. 3, 55, (1998)	At 50.00 ppm. Woody, guaiacol, smoky, astringent and phenolic with vanillin and coumarin nuances

Potential Uses

Applications	flavor and fragrance agents
Odor purposes	Acacia, Allspice, Almond, Alpine bouquet, Amber, Ambreine, Animal, Autumn, Azalea, Balsam, Bayberry, Beeswax absolute replacer, Bouquet, Boxwood berry, Cabreuva wood, Calamus oil replacer, Carnation, Cassia, Cassia blossom, Castoreum, Champaca, Chestnut blossom, Christmas, Cigar, Cistus, Clove, Clove blossom, Copaiba balsam, Coronilla, Country meadow, Cyclamen, Deertongue absolute replacer, Dogwood, Fern, Fig, Flouve, Flouve blossom, Forest, Ginger white ginger, Guaiacwood, Gurjun balsam, Habuba, Hawthorn, Hay new mown hay, Heather, Hinoki oil replacer, Hugonia, Incense, Iris blossom, Jonquil, Labdanum, Millefleurs, Moss, Musk, Opoponax, Oriental, Orris, Osmanthus, Petunia, Phlox, Pinion, Rose, Rose moss rose, Rose tea rose, Rose white rose, Sherry, Spice, Sweet grass, Tobacco, Tonka bean, Valerian, Vanilla, Wine, Woodruff, Woody, Yerba mate
Flavoring purposes	Barley, Cheese, Chocolate cocoa, Cistus, Cookie, Copaiba balsam, Guaiacwood, Meat smoked meat, Praline, Smoke, Tea, Valerian, Yerba mate
Other purposes	Tea china
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:
Not determined
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 guaiacyl acetate usage levels up to:
	2.0000 % in the fragrance concentrate.

Maximised Survey-derived Daily Intakes (MSDI-EU):		0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		0.10 (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: 13
Click here to view publication 13
		average usual ppm	average maximum ppm
baked goods:		-	15.20000
beverages(nonalcoholic):		-	10.00000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	9.59000
fruit ices:		-	-
gelatins / puddings:		-	10.00000
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	-
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:		-	11.20000
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

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):613-70-7

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :61155

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

(2-methoxyphenyl) acetate

Chemidplus:0000613707