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para-vanillyl alcohol

General Material Information

Preferred name	para-vanillyl alcohol
Trivial Name	Vanillyl alcohol
Short Description	p-vanillin alcohol
Formula	C8 H10 O3
CAS Number	498-00-0
FEMA Number	3737
Flavis Number	2.213
ECHA Number	207-852-4
FDA UNII	X7EA1JUA6M
Nikkaji Number	J28.483A
Beilstein Number	1910044
MDL	MFCD00004659
COE Number	690
Bio Activity Summary	External link
NMR Predictor	External link
JECFA Food Flavoring	886 vanillyl alcohol
FDA Patent	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm	498-00-0 ; VANILLYL ALCOHOL
Synonyms	benzenemethanol, 4-hydroxy-3-methoxy- 4-hydroxy-3-methoxy-benzenemethanol 4-hydroxy-3-methoxy-benzyl alcohol 4-hydroxy-3-methoxybenzene methanol 4-hydroxy-3-methoxybenzenemethanol 4-hydroxy-3-methoxybenzyl alcohol 4-hydroxy-3-methoxybenzylalcohol 4-hydroxy-3-methoxyphenyl methanol 4-hydroxy-3-methoxyphenylmethanol 4-hydroxymethyl-2-methoxy-phenol 4-( hydroxymethyl)-2-methoxyphenol 3-methoxy-4-hydroxybenzyl alcohol para- vanillic alcohol p- vanillin alcohol para- vanillin alcohol vanillyl alcohol p- vanillyl alcohol 4-(hydroxymethyl)-2-methoxyphenol 4-Hydroxy-3-methoxybenzenemethanol 3-Methoxy-4-hydroxybenzyl alcohol Vanillic alcohol 4-Hydroxy-3-methoxybenzyl alcohol Vanillin alcohol V 0018 V 0018 (alcohol) NSC 3993 p-(Hydroxymethyl)guaiacol 3-Methoxy-4-hydroxybenzenemethanol 3-Methoxyl-4-hydroxybenzyl alcohol

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

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Literature & References

	4-(hydroxymethyl)-2-methoxyphenol
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	498-00-0
Pubchem (cid):	62348
Pubchem (sid):	135019885

Publications by PubMed
Therapeutic use of H2O2-responsive anti-oxidant polymer nanoparticles for doxorubicin-induced cardiomyopathy.
Importance of glucose-6-phosphate dehydrogenase (G6PDH) for vanillin tolerance in Saccharomyces cerevisiae.
[Phenolic derivatives from Wisteria sinensis sweet caulis].
Inhibitory activity of carbonyl compounds on alcoholic fermentation by Saccharomyces cerevisiae.
Expression profiles of key phenylpropanoid genes during Vanilla planifolia pod development reveal a positive correlation between PAL gene expression and vanillin biosynthesis.
Structural variation of bamboo lignin before and after ethanol organosolv pretreatment.
Evaluation of nonionic adsorbent resins for removal of inhibitory compounds from corncob hydrolysate for ethanol fermentation.
Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs).
[Chemical constituents of Conioselinum vaginatum].
On the factors affecting product distribution in laccase-catalyzed oxidation of a lignin model compound vanillyl alcohol: experimental and computational evaluation.
Anxiolytic property of Lactuca sativa, effect on anxiety behaviour induced by novel food and height.
[Application of the vanillin sulfuric acid colorimetry-ultraviolet spectrometry on quality evaluation of Panax notoginseng].
[Study on chemical composition of ethylacetate fraction from Polygonum amplexicaule var. sinense].
Biotransformation of rice bran to ferulic acid by pediococcal isolates.
Differences in the phenolic composition and antioxidant properties between Vitis coignetiae and Vitis vinifera seeds extracts.
Exploration of Vanilla pompona from the Peruvian Amazon as a potential source of vanilla essence: quantification of phenolics by HPLC-DAD.
Phenolic compounds in particles of mainstream waterpipe smoke.
Effects of alcohol compounds on the growth and lipid accumulation of oleaginous yeast Trichosporon fermentans.
Influence of the environment on the protective effects of guaiacol derivatives against oxidative stress: mechanisms, kinetics, and relative antioxidant activity.
Polymeric proanthocyanidins in skins and seeds of 37 Vitis vinifera L. cultivars: a methodological comparative study.
Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry.
Deactivation of cellulases by phenols.
Ethnobotanical survey, chemical composition, and antioxidant capacity of methanolic extract of the root bark of Annona cuneata Oliv.
Pseudomonas resinovorans SPR1, a newly isolated strain with potential of transforming eugenol to vanillin and vanillic acid.
[Study on the chemical constituents of Antipathes dichotoma].
Miscanthus x giganteus bark organosolv fractionation: fate of lipophilic components and formation of valuable phenolic byproducts.
Aroma characteristics of cocoa tea (Camellia ptilophylla Chang).
The Zymomonas mobilis regulator hfq contributes to tolerance against multiple lignocellulosic pretreatment inhibitors.
Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots.
Antioxidant activity of a red lentil extract and its fractions.
Anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata Bl.
[Olfactory functional magnetic resonance imaging with modified OEP-98C olfactometer and event-related design].
Effects of biomass hydrolysis by-products on oleaginous yeast Rhodosporidium toruloides.
Miscanthus x giganteus extractives: a source of valuable phenolic compounds and sterols.
Scale-up of counter-current chromatography: demonstration of predictable isocratic and quasi-continuous operating modes from the test tube to pilot/process scale.
Detoxification of model phenolic compounds in lignocellulosic hydrolysates with peroxidase for butanol production from Clostridium beijerinckii.
Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy.
New 18-l process-scale counter-current chromatography centrifuge.
New oxidase from Bjerkandera arthroconidial anamorph that oxidizes both phenolic and nonphenolic benzyl alcohols.
Mononuclear Ru(III) Schiff base complexes: synthesis, spectral, redox, catalytic and biological activity studies.
Reactions of tertiary phosphines with alcohols in aqueous media.
[Studies on the chemical constituents of Litsea lancifolia].
Focused microwaves-assisted extraction and simultaneous spectrophotometric determination of vanillin and p-hydroxybenzaldehyde from vanilla fragans.
Capsaicin prevents ethanol-induced teratogenicity in cultured mouse whole embryos.
Structural analogues of homoeriodictyol as flavor modifiers. Part III: short chain gingerdione derivatives.
Two Greek siblings with sepiapterin reductase deficiency.
A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism.
Deposition of lipid, protein, and secretory phospholipase A2 on hydrophilic contact lenses.
Effect of phenolic aldehydes and flavonoids on growth and inactivation of Oenococcus oeni and Lactobacillus hilgardii.
Retronasal but not oral-cavity-only identification of "purely olfactory" odorants.
Metabolic characterization of newly isolated Pseudomonas nitroreducens Jin1 growing on eugenol and isoeugenol.
Studies on the antioxidant activities of natural vanilla extract and its constituent compounds through in vitro models.
[Role of sympathetic nerve activity and arterial endothelial function in pathogenesis of hypertension in patients with obstructive sleep apnea-hypopnea syndrome].
Effect of natural phenol derivatives on skeletal type sarcoplasmic reticulum Ca2+ -ATPase and ryanodine receptor.
Influence of inhibitory compounds and minor sugars on xylitol production by Debaryomyces hansenii.
Final report on the safety assessment of capsicum annuum extract, capsicum annuum fruit extract, capsicum annuum resin, capsicum annuum fruit powder, capsicum frutescens fruit, capsicum frutescens fruit extract, capsicum frutescens resin, and capsaicin.
Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.
Queen pheromone modulates brain dopamine function in worker honey bees.
The neural representation of odor is modulated by the presence of a trigeminal stimulus during odor encoding.
Solubility of the sesquiterpene alcohol patchoulol in supercritical carbon dioxide.
Quantitative determination of phyllanthin and hypophyllanthin in Phyllanthus species by high-performance thin layer chromatography.
Anti-inflammatory action of phenolic compounds from Gastrodia elata root.
Metabolic diversion of the phenylpropanoid pathway causes cell wall and morphological changes in transgenic tobacco stems.
Reduction of carboxylic acids by Nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme.
Non-cannabinoid CB1, non-cannabinoid CB2 antinociceptive effects of several novel compounds in the PPQ stretch test in mice.
Under the influence of the active deodorant ingredient 4-hydroxy-3-methoxybenzyl alcohol, the skin bacterium Corynebacterium jeikeium moderately responds with differential gene expression.
The prediction of isotopic patterns in phenylpropanoids from their precursors and the mechanism of the NIH-shift: basis of the isotopic characteristics of natural aromatic compounds.
Gene silencing of cinnamyl alcohol dehydrogenase in Pinus radiata callus cultures.
Conversion of isoeugenol into vanillic acid by Pseudomonas putida I58 cells exhibiting high isoeugenol-degrading activity.
Metabolic regulation at the tricarboxylic acid and glyoxylate cycles of the lignin-degrading basidiomycete Phanerochaete chrysosporium against exogenous addition of vanillin.
Isolation of antioxidant compounds from the methanolic extract of the roots of Decalepis hamiltonii (Wight and Arn.).
Crystal structure of 6-hydroxy-D-nicotine oxidase from Arthrobacter nicotinovorans.
HPLC determination of salinomycin and related compounds in fermentation media of Streptomyces albus and premixes.
Spectral and catalytic properties of aryl-alcohol oxidase, a fungal flavoenzyme acting on polyunsaturated alcohols.
Characterization of Sphingomonas aldehyde dehydrogenase catalyzing the conversion of various aromatic aldehydes to their carboxylic acids.
Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem.
Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.
Comparison between cachaça and rum using pattern recognition methods.
Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.
NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins.
A novel potato defence-related alcohol:NADP+ oxidoreductase induced in response to Erwinia carotovora.
Lignin degradation in a compost environment by the deuteromycete Paecilomyces inflatus.
Characterization of an extracellular salicyl alcohol oxidase from larval defensive secretions of Chrysomela populi and Phratora vitellinae (Chrysomelina).
Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast.
O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction.
New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes.
Characterization of the eugenol hydroxylase genes (ehyA/ehyB) from the new eugenol-degrading Pseudomonas sp. strain OPS1.
Tuning of the product spectrum of vanillyl-alcohol oxidase by medium engineering.
Stability of capsinoid in various solvents.
Contribution of C-fibers to leucocyte recruitment in bronchoalveolar lavage fluid and pleural cavity in the rat.
Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines.
Anticonvulsive and free radical scavenging activities of vanillyl alcohol in ferric chloride-induced epileptic seizures in Sprague-Dawley rats.
Inversion of stereospecificity of vanillyl-alcohol oxidase.
Asp-170 is crucial for the redox properties of vanillyl-alcohol oxidase.
Effect of alcohol compounds found in hemicellulose hydrolysate on the growth and fermentation of ethanologenic Escherichia coli.
[Effect of aromatic compounds and Mn2+ on the ligninolytic enzyme complex from the fungus Pleurotus floridae (FRIES) Kummer--a white-rot wood fungus].
Effect of selected aldehydes on the growth and fermentation of ethanologenic Escherichia coli.
Spatiotemporal masking in pure olfaction.
Activation by Phoneutria nigriventer spider venom of autonomic nerve fibers in the isolated rat heart.
Ferulic acid dehydrodimers from wheat bran: isolation, purification and antioxidant properties of 8-O-4-diferulic acid.
Regio- and stereospecific conversion of 4-alkylphenols by the covalent flavoprotein vanillyl-alcohol oxidase.
Relation of olfactory event-related potentials to changes in stimulus concentration.
Kinetic mechanism of vanillyl-alcohol oxidase with short-chain 4-alkylphenols.
Molecular cloning, sequencing, and heterologous expression of the vaoA gene from Penicillium simplicissimum CBS 170.90 encoding vanillyl-alcohol oxidase.
Enantioseparation using apoenzymes immobilized in a porous polymeric membrane.
Catalytic mechanism of the oxidative demethylation of 4-(methoxymethyl)phenol by vanillyl-alcohol oxidase. Evidence for formation of a p-quinone methide intermediate.
Enigmatic Gratuitous Induction of the Covalent Flavoprotein Vanillyl-Alcohol Oxidase in Penicillium simplicissimum.
Mercuration of vanillyl-alcohol oxidase from Penicillium simplicissimum generates inactive dimers.
A simplified routine assay for urinary 3-methoxy-4-hydroxyphenylglycol.
Comparison of the Efficacies of Chloromethane, Methionine, and S-Adenosylmethionine as Methyl Precursors in the Biosynthesis of Veratryl Alcohol and Related Compounds in Phanerochaete chrysosporium.
Bidirectional transformation of aromatic aldehydes by Desulfovibrio desulfuricans under nitrate-dissimilating conditions.
Substrate specificity of flavin-dependent vanillyl-alcohol oxidase from Penicillium simplicissimum. Evidence for the production of 4-hydroxycinnamyl alcohols from 4-allylphenols.
Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer,Eldana saccharina walker (Lepidoptera: Pyralidae).
Antioxidant and pro-oxidant activities of p-hydroxybenzyl alcohol and vanillin: effects on free radicals, brain peroxidation and degradation of benzoate, deoxyribose, amino acids and DNA.
Manganese(II) oxidation by manganese peroxidase from the basidiomycete Phanerochaete chrysosporium. Kinetic mechanism and role of chelators.
Oxidation of phenolic arylglycerol beta-aryl ether lignin model compounds by manganese peroxidase from Phanerochaete chrysosporium: oxidative cleavage of an alpha-carbonyl model compound.
An Agrobacterium two-component regulatory system for the detection of chemicals released from plant wounds.
Oxidation of aromatic alcohols by purified methanol dehydrogenase from Methylosinus trichosporium.
Devil's-claw (Proboscidea louisianica), essential oil and its components : Potential allelochemical agents on cotton and wheat.
Biotransformations of aromatic aldehydes by acetogenic bacteria.
Oxidation of Lignin-Related Aromatic Alcohols by Cell Suspensions of Methylosinus trichosporium.
Thiol-mediated oxidation of nonphenolic lignin model compounds by manganese peroxidase of Phanerochaete chrysosporium.
Divanillates and polymerizable vanillates as ingredients of dental cements.
[Excitable actions of counterirritants on cutaneous sensation].
Studies on the kinetics of cyanohydrin synthesis and cleavage by the the flavoenzyme oxynitrilase.
Effect of diet on urinary excretion of VMA, HVA, metanephrine, and total free catecholamine in normal preschool children.

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
CHEBI:	View
Metabolomics Database:	Search
UM BBD:	Search
KEGG (GenomeNet):	C06317
HMDB (The Human Metabolome Database):	HMDB32012
FooDB:	FDB008710
YMDB (Yeast Metabolome Database):	YMDB01712
Export Tariff Code:	2909.50.5000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

Alfa Biotechnology	Anhui Haibei
Axxence Aromatic	Beijing Lys Chemicals
BOC Sciences	Carbosynth
EMD Millipore	Ernesto Ventós
Excellentia International	ExtraSynthese
Kingchem Laboratories	Lluch Essence
M&U International	Penta International
Prodasynth	Santa Cruz Biotechnology
Shijiazhuang Donglian Nankai Aroma Chemicals	Sigma-Aldrich
Synerzine	TCI AMERICA
Tianjin Danjun International	United International
WholeChem	Axxence Aromatic GmbH
Beijing Lys Chemicals Co, LTD.	Lluch Essence S.L.
M&U International LLC	Penta International Corporation
Synerzine, Inc.	Tianjin Danjun International Trade Co., LTD.
Qingdao Free Trade Zone United International Co Ltd	Ernesto Ventós S.A.
WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	154.16529846191
Melting Point	112 to 115°C @ 760 mm Hg
Boiling Point	312 to 313°C @ 760 mm Hg
Vapor Pressure	0.000216 mmHg @ 25 °C
Flash Point TCC Value	142.78 °C TCC
logP (o/w)	0.42
Solubility
alcohol	Yes
water, 2000 mg/L @ 20 °C (exp)	Yes

Organoleptic Properties

Odor Type: Creamy
sweet, creamy, vanilla, caramellic, graham cracker, tonka, milky, powdery, phenolic, coconut
Luebke, William tgsc, (2017)	At 100.00 %. sweet creamy vanilla caramellic coconut graham cracker tonka milky powdery
Mosciano, Gerard P&F 17, No. 5, 127, (1992)	Sweet, creamy, phenolic with a vanilla and coconut nuance
Flavor Type: Creamy
sweet, creamy, custard, vanilla, milky, powdery
Luebke, William tgsc, (2017)	Sweet creamy custard vanilla milky powdery
Mosciano, Gerard P&F 17, No. 5, 127, (1992)	Sweet, creamy, milky with a slight powdery mouthfeel

Occurrences

Potential Uses

Applications	flavor and fragrance agents
Odor purposes	Balsam, Coconut, Cream, Vanilla
Flavoring purposes	Milk, Sweet

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 para-vanillyl alcohol usage levels up to:
	8.0000 % in the fragrance concentrate.

Maximised Survey-derived Daily Intakes (MSDI-EU):		5.40 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		6.00 (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:		-	12.00000
beverages(nonalcoholic):		-	12.00000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	12.00000
fruit ices:		-	-
gelatins / puddings:		-	12.00000
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:		-	12.00000
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) on a request from the Commission related to Flavouring Group Evaluation 20 (FGE.20): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23
View page or View pdf

Flavouring Group Evaluation 52 (FGE.52): Consideration of hydroxy- and alkoxy-substituted benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters evaluated by EFSA in FGE.20 (2005) (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 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):498-00-0

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :62348

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

4-(hydroxymethyl)-2-methoxyphenol

Chemidplus:0000498000