Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | pale yellow clear liquid (est) |
Assay: | 98.00 to 100.00 %
|
Food Chemicals Codex Listed: | No |
Specific Gravity: | 1.09000 to 1.10000 @ 25.00 °C.
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Pounds per Gallon - (est).: | 9.070 to 9.153
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Refractive Index: | 1.53400 to 1.54000 @ 20.00 °C.
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Melting Point: | 5.00 °C. @ 760.00 mm Hg
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Boiling Point: | 221.00 to 222.00 °C. @ 760.00 mm Hg
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Vapor Pressure: | 0.078000 mmHg @ 25.00 °C. (est) |
Flash Point: | 211.00 °F. TCC ( 99.44 °C. )
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logP (o/w): | 1.925 (est) |
Shelf Life: | 24.00 month(s) or longer if stored properly. |
Storage: | store in cool, dry place in tightly sealed containers, protected from heat and light. |
Soluble in: |
| alcohol | | water, 2093 mg/L @ 25 °C (est) |
Organoleptic Properties:
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Odor Type: spicy |
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Odor Strength: | medium , recommend smelling in a 10.00 % solution or less |
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Substantivity: | 132 hour(s) at 10.00 % in dipropylene glycol |
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| spicy clove vanilla phenolic medicinal leathery woody smoky burnt |
Odor Description: at 10.00 % in dipropylene glycol. | spicy clove vanilla phenolic medicinal leathery woody smoky burnt Luebke, William tgsc, (2021) |
|
| sweet candy spicy clove vanilla leathery spicy smoky |
Odor Description: at 1.00 % in ethyl alcohol. | Sweet, candy, spice, eugenol, vanilla, leather, spicy, smoky Mosciano, Gerard P&F 23, No. 6, 31, (1998) |
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Flavor Type: spicy |
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| spicy clove woody leathery smoky coffee phenolic cocoa burnt |
Taste Description:
| spicy clove woody leathery smoky coffee phenolic cocoa burnt Luebke, William tgsc, (2021) |
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| vanilla spicy clove woody leathery chemical |
Taste Description: at 10.00 ppm. | VaniIla, spice, eugenol, woody and leather nuances with no residual chemical notes Mosciano, Gerard P&F 23, No. 6, 31, (1998) |
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Odor and/or flavor descriptions from others (if found). |
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Sigma-Aldrich |
2-Methoxy-4-methylphenol, ≥98%, FG |
Odor Description: | carnation; cheese; chocolate; clove; jasmine; sweet; vanilla; meaty; woody; wine-like; green; smoky; coffee |
|
R C Treatt & Co Ltd |
4-Methylguaiacol Halal, Kosher |
Odor Description: | sweet, spicy/phenolic vanilla |
Taste Description: | spicy Used in rum, nut, clove, vanilla flavours for savoury at 35ppm, soft confection at 10ppm, beverages at 5ppm, and dairy confection/desserts at 2ppm. |
|
Symrise |
Methyl guaiacol-4 |
Odor Description: | sweet-spicy, phenolic-leathery note, floral balsamic undertones |
Taste Description: | phenolic, smoky, sweet, coffee, vanilla, cocoa Useful in: brown nuts, brown cocoa, brown coffee, brown others, dairy, vanilla, savory spices, savory meat, sweet others, alcoholics. |
|
Moellhausen |
CRESOL |
Odor Description: | aromatic, spicy, clove, vanilla, phenolic, smoke-like |
Taste Description: | spicy, medicinal; vanilla, clove-like with phenolic nuances |
|
Perfumery Laboratory |
VALSPICE |
Odor Description: | sweet, smoky, leathery fragrance with hints of vanilla and cloves |
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Cosmetic Information:
Suppliers:
Advanced Biotech |
4 METHYL GUAIACOL SYNTHETIC
98% min. Odor: Spicy, Vanilla, Leather |
Advanced Biotech |
4-METHYL GUAIACOL NATURAL
98% min. Odor: Spicy, Sweet |
Ambles Nature et Chimie |
4 METHYL GUAIACOL
|
Anhui Haibei |
4-Methyl Guaiacol natural
|
Anhui Haibei |
Creosol
|
Anhui Suzhou Jinli Aromatic Chemicals |
4-Methyl Guaiacol
Odor: soy sauce, smoked, wood sweet |
Aurochemicals |
4-METHYL GUAIACOL, Natural
|
Beijing Lys Chemicals |
2-Methoxy-4-methylphenol (natural)
|
Beijing Lys Chemicals |
4-Methyl guaiacol
|
BOC Sciences |
For experimental / research use only. |
2-Methoxy-4-methylphenol
|
Charkit Chemical |
METHOXY-4-METHYLPHENOL, 2- (CRESOL) M0300 FEMA 2671
|
Diffusions Aromatiques |
CREOSOL NATUREL
|
Endeavour Specialty Chemicals |
4-Methylguaiacol 99%
|
Speciality Chemical Product Groups |
Ernesto Ventós |
CREOSOL NATURAL
Odor: SMOKY, SWEET, BURNT |
Foreverest Resources |
4-Methyl Guaiacol
|
Foreverest Resources |
Creosol (Valspice) 98%
|
Frinton Laboratories |
For experimental / research use only. |
4-Methylguaiacol
|
Fuzhou Farwell |
4-Methylguaiacol
|
Jiangyin Healthway |
4-Methyl Guaiacol
|
New functional food ingredients |
Jinan Enlighten Chemical Technology(Wutong Aroma ) |
4-Methyl guaiacol, Kosherk
|
K.L. Koh Enterprise |
4-METHYL GUAIACOL
|
Lluch Essence |
4-METHYL GUAIACOL NATURAL
|
Lluch Essence |
CREOSOL 98%
Odor: CLOVE, SPICY, PHENOLIC |
M&U International |
NAT.4-METHYL GUAIACOL, Kosher
|
Moellhausen |
CRESOL
Odor: aromatic, spicy, clove, vanilla, phenolic, smoke-like Flavor: spicy, medicinal; vanilla, clove-like with phenolic nuances |
Natural Advantage |
Creosol Nat
Flavor: burnt, phenolic, smoky, spicy, sweet, vanilla |
Riverside Aromatics LTD.is the exclusive distributor for Europe in UK for any non-US based inquiries |
OQEMA |
4-Methyl Guaiacol
|
Pearlchem Corporation |
Natural 4-Methyl Guaiacol
|
Penta International |
VALSPICE NATURAL
|
Penta International |
VALSPICE
|
Perfumery Laboratory |
VALSPICE
Odor: sweet, smoky, leathery fragrance with hints of vanilla and cloves |
R C Treatt & Co Ltd |
4-Methylguaiacol
Halal, Kosher Odor: sweet, spicy/phenolic vanilla Flavor: spicy Used in rum, nut, clove, vanilla flavours for savoury at 35ppm, soft confection at 10ppm, beverages at 5ppm, and dairy confection/desserts at 2ppm. |
Reincke & Fichtner |
2-Methoxy-4-methylphenol
|
Reincke & Fichtner |
4-Methoxy-4-methylphenol natural
|
Riverside Aromatics |
4-METHYLGUAIACOL (CREOSOL), NATURAL
|
Riverside Aromatics |
4-METHYLGUAIACOL
|
Robinson Brothers |
4-Methylguaiacol
|
https://www.robinsonbrothers.uk/chemistry-competences |
Sigma-Aldrich |
2-Methoxy-4-methylphenol, ≥98%, FG
Odor: carnation; cheese; chocolate; clove; jasmine; sweet; vanilla; meaty; woody; wine-like; green; smoky; coffee |
Certified Food Grade Products |
Sigma-Aldrich |
2-Methoxy-4-methylphenol, natural, 97%, FG
|
Sunaux International |
nat.4-Methyl Guaiacol
|
Symrise |
Methyl guaiacol-4
Odor: sweet-spicy, phenolic-leathery note, floral balsamic undertones Flavor: phenolic, smoky, sweet, coffee, vanilla, cocoa Useful in: brown nuts, brown cocoa, brown coffee, brown others, dairy, vanilla, savory spices, savory meat, sweet others, alcoholics. |
Synerzine |
2-Methoxy-4-methylphenol
|
TCI AMERICA |
For experimental / research use only. |
2-Methoxy-4-methylphenol >98.0%(GC)
|
Tengzhou Jitian Aroma Chemiclal |
4-Methyl Guaiacol
|
Tengzhou Xiang Yuan Aroma Chemicals |
4-Methyl Guaiacol
|
The Perfumers Apprentice |
Valspice (4 Methyl Guaiacol)
Odor: This is a beautiful spicy, smokey (campfire smoke) fragrance with nuances of deep fruit and leather |
United International |
4-Methyl Guaiacol Nat.
|
Vigon International |
Creosol (Valspice)
Odor: Spice clove vanilla phenolic medical leather |
WEN International |
2-METHOXY-4-METHYLPHENOL Natural
|
WholeChem |
4-Methyl guaiacol
|
Safety Information:
Preferred SDS: View |
European information : |
Most important hazard(s): | Xn - Harmful. |
R 22 - Harmful if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. 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 37/39 - Wear suitable gloves and eye/face protection.
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
Acute toxicity, Oral (Category 4), H302 Skin irritation (Category 2), H315 Eye irritation (Category 2A), H319 Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
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GHS Label elements, including precautionary statements |
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Pictogram | |
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Signal word | Warning |
Hazard statement(s) |
H302 - Harmful if swallowed H315 - Causes skin irritation H319 - Causes serious eye irritation H335 - May cause respiratory irritation
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Precautionary statement(s) |
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P264 - Wash skin thouroughly after handling. P270 - Do not eat, drink or smoke when using this product. P271 - Use only outdoors or in a well-ventilated area. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. 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. P330 - Rinse mouth. 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.
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Oral/Parenteral Toxicity: |
oral-rat LD50 740 mg/kg Folia Medica Cracoviensia. Vol. 32, Pg. 309, 1991.
intravenous-mouse LD50 76 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
LUNGS, THORAX, OR RESPIRATION: DYSPNEA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 30, 1966.
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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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 |
IFRA Critical Effect: | Dermal sensitization |
IFRA: | View Standard |
View IFRA Standards Library for complete information. |
Please review Amendment 49 IFRA documentation for complete information. |
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%): |
Category 1: Products applied to the lips |
0.0085 % |
Category 2: Products applied to the axillae |
0.0025 % |
Category 3: Products applied to the face/body using fingertips |
0.051 % |
Category 4: Products related to fine fragrance |
0.047 % |
| Category 5: Products applied to the face and body using the hands (palms), primarily leave-on |
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on |
0.012 % |
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on |
0.012 % |
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on |
0.012 % |
Category 5D: Baby Creams, baby Oils and baby talc |
0.012 % |
Category 6: Products with oral and lip exposure |
0.028 % |
| Category 7: Products applied to the hair with some hand contact |
Category 7A: Rinse-off products applied to the hair with some hand contact |
0.096 % |
Category 7B: Leave-on products applied to the hair with some hand contact |
0.096 % |
Category 8: Products with significant anogenital exposure |
0.005 % |
Category 9: Products with body and hand exposure, primarily rinse off |
0.092 % |
| Category 10: Household care products with mostly hand contact |
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products) |
0.33 % |
Category 10B: Household aerosol/spray products |
0.33 % |
| Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate |
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure |
0.18 % |
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure |
0.18 % |
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin |
No Restriction |
| Notes: |
IFRA FLAVOR REQUIREMENTS: |
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards. |
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Maximised Survey-derived Daily Intakes (MSDI-EU): | 31.00 (μg/capita/day) |
Maximised Survey-derived Daily Intakes (MSDI-USA): | 3.00 (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: 3. Update in publication number(s): 29 |
Click here to view publication 3 |
| average usual ppm | average maximum ppm |
baked goods: | 4.00000 | 11.00000 |
beverages(nonalcoholic): | 10.00000 | 21.00000 |
beverages(alcoholic): | 0.60000 | 10.00000 |
breakfast cereal: | - | - |
cheese: | - | - |
chewing gum: | 15.00000 | 25.00000 |
condiments / relishes: | - | - |
confectionery froastings: | - | - |
egg products: | - | - |
fats / oils: | - | - |
fish products: | - | - |
frozen dairy: | 1.00000 | 2.00000 |
fruit ices: | - | - |
gelatins / puddings: | 7.00000 | 18.00000 |
granulated sugar: | - | - |
gravies: | - | - |
hard candy: | 0.80000 | 0.80000 |
imitation dairy: | - | - |
instant coffee / tea: | - | - |
jams / jellies: | - | - |
meat products: | 12.00000 | 35.00000 |
milk products: | - | - |
nut products: | - | - |
other grains: | - | - |
poultry: | - | - |
processed fruits: | - | - |
processed vegetables: | - | - |
reconstituted vegetables: | - | - |
seasonings / flavors: | - | - |
snack foods: | - | - |
soft candy: | 4.00000 | 10.00000 |
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) 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 |
Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006) 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 |
Scientific Opinion on the safety and efficacy of phenol derivatives containing ring-alkyl, ring-alkoxy and side-chains with an oxygenated functional group (chemical group 25) when used as flavourings for all species View page or View pdf |
EPI System: | View |
AIDS Citations: | Search |
Cancer Citations: | Search |
Toxicology Citations: | Search |
EPA Substance Registry Services (TSCA): | 93-51-6 |
EPA ACToR: | Toxicology Data |
EPA Substance Registry Services (SRS): | Registry |
Laboratory Chemical Safety Summary : | 7144 |
National Institute of Allergy and Infectious Diseases: | Data |
WGK Germany: | 3 |
| 2-methoxy-4-methylphenol |
Chemidplus: | 0000093516 |
RTECS: | GP1755000 for cas# 93-51-6 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
homo | catechol monomethyl ether | | creosol | p- | creosol | para- | creosol | | creosol natural | homo | guaiacol | | guaiacol, 4-methyl- | 1- | hydroxy-2-methoxy-4-methyl benzene | 1- | hydroxy-2-methoxy-4-methylbenzene | 4- | hydroxy-3-methoxy-1-methyl benzene | 4- | hydroxy-3-methoxytoluene | 4- | hydroxy-3-methylanisol | 2- | hydroxy-5-methylanisole | 2- | methoxy-4-cresol | 3- | methoxy-4-hydroxytoluene | 2- | methoxy-4-methyl phenol | 2- | methoxy-4-methylphenol | 2- | methoxy-4-methylphenol natural | 2- | methoxy-p-cresol | 2- | methoxy-para-cresol | 4- | methyl guaiacol | nat.4- | methyl guaiacol | p- | methyl guaiacol | para- | methyl guaiacol | 4- | methyl guaiacol natural | 4- | methyl guaiacol synthetic | 4- | methyl-2-methoxyphenol | 4- | methylguaiacol | p- | methylguaiacol | para- | methylguaiacol | | phenol, 2-methoxy-4-methyl- | | rohkcrsol | | valspice (Givaudan) | | valspice natural |
Articles:
PubMed: | Volatile composition and sensory properties of Vanilla × tahitensis bring new insights for vanilla quality control. |
PubMed: | Effect of Carbonyl Inhibitors and Their H2O 2 Detoxification on Lactic Acid Fermentation. |
PubMed: | Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII). |
PubMed: | Spectrophotometric determination of irrigant extrusion using passive ultrasonic irrigation, EndoActivator, or syringe irrigation. |
PubMed: | Microwave-assisted deuterium exchange: the convenient preparation of isotopically labelled analogues for stable isotope dilution analysis of volatile wine phenols. |
PubMed: | Hydrogenation of biofuels with formic acid over a palladium-based ternary catalyst with two types of active sites. |
PubMed: | Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines. |
PubMed: | Extraction of phenols from lignin microwave-pyrolysis oil using a switchable hydrophilicity solvent. |
PubMed: | Ion permeability of artificial membranes evaluated by diffusion potential and electrical resistance measurements. |
PubMed: | Bamboo vinegar decreases inflammatory mediator expression and NLRP3 inflammasome activation by inhibiting reactive oxygen species generation and protein kinase C-α/δ activation. |
PubMed: | Ultraviolet spectroscopy of fundamental lignin subunits: guaiacol, 4-methylguaiacol, syringol, and 4-methylsyringol. |
PubMed: | Polycyclic aromatic hydrocarbons (PAH) and phenolic substances in meat products smoked with different types of wood and smoking spices. |
PubMed: | In chemico evaluation of prohapten skin sensitizers: behavior of 2-methoxy-4-(¹³C)methylphenol in the peroxidase peptide reactivity assay (PPRA) as an alternative to animal testing. |
PubMed: | Synthesis, characterization, and cure chemistry of renewable bis(cyanate) esters derived from 2-methoxy-4-methylphenol. |
PubMed: | Exposure of grapes to smoke of vegetation with varying lignin composition and accretion of lignin derived putative smoke taint compounds in wine. |
PubMed: | Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry. |
PubMed: | Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine. |
PubMed: | Synthesis of renewable bisphenols from creosol. |
PubMed: | Classification of smoke tainted wines using mid-infrared spectroscopy and chemometrics. |
PubMed: | Contents of polycyclic aromatic hydrocarbons (PAH) and phenolic substances in Frankfurter-type sausages depending on smoking conditions using glow smoke. |
PubMed: | Shoo fly, don't bother me! Efficacy of traditional methods of protecting cattle from tsetse. |
PubMed: | Occupational exposure to phenolic compounds at coke plants--urinary excretion of methoxyphenols as an indicator of exposure to methoxyphenols. |
PubMed: | Field trial of a synthetic tsetse-repellent technology developed for the control of bovine trypanosomosis in Kenya. |
PubMed: | Preferential inhibition by antidiarrheic 2-methoxy-4-methylphenol of Ca(2+) influx across acquired N-methyl-D-aspartate receptor channels composed of NR1/NR2B subunit assembly. |
PubMed: | Determination of Eucalyptus spp lignin S/G ratio: a comparison between methods. |
PubMed: | Photochemistry of tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-ones: an efficient general route to substituted linear triquinanes from 2-methoxyphenols. Total synthesis of (+/-)-Delta(9(12))-capnellene. |
PubMed: | Volatile composition of Merlot wine from different vine water status. |
PubMed: | Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke. |
PubMed: | Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane. |
PubMed: | Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine. |
PubMed: | The reactivity of ortho-methoxy-substituted catechol radicals with sulfhydryl groups: contribution for the comprehension of the mechanism of inhibition of NADPH oxidase by apocynin. |
PubMed: | Cytoprotective properties of phenolic antidiarrheic ingredients in cultured astrocytes and neurons of rat brains. |
PubMed: | A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.). |
PubMed: | Tsetse and other biting fly responses to Nzi traps baited with octenol, phenols and acetone. |
PubMed: | Oral administration of phenolic antidiarrheic ingredients prevents ovariectomy-induced bone loss. |
PubMed: | Thermal stabilization of levoglucosan in aromatic substances. |
PubMed: | Flavor characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process. |
PubMed: | Occupational exposure to toluene and its possible causative role in renal damage development in shoe workers. |
PubMed: | Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin. |
PubMed: | The effects of sample preparation and gas chromatograph injection techniques on the accuracy of measuring guaiacol, 4-methylguaiacol and other volatile oak compounds in oak extracts by stable isotope dilution analyses. |
PubMed: | Degradation of phenol and cresols at low temperatures using a suspended-carrier biofilm process. |
PubMed: | Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. |
PubMed: | Wood creosote, the principal active ingredient of seirogan, an herbal antidiarrheal medicine: a single-dose, dose-escalation safety and pharmacokinetic study. |
PubMed: | Simultaneous determination of 2-methoxyphenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol and 4'-hydroxy-3'-methoxyacetophenone in urine by capillary gas chromatography. |
PubMed: | Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage. |
PubMed: | [Wood creosote: a historical study and its preparation in combination with herbal drugs]. |
PubMed: | Lack of oncogenicity of wood creosote, the principal active ingredient of Seirogan, an herbal antidiarrheal medication, in Sprague-Dawley rats. |
PubMed: | The first total synthesis of (+/-)-eremopetasidione. |
PubMed: | Enzymatic synthesis of vanillin. |
PubMed: | Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. |
PubMed: | Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure. |
PubMed: | Comparison of the antidiarrheal effects of wood creosote and loperamide in the rat jejunum and colon in vitro. |
PubMed: | Anti-diarrhoeal effects of seirogan in the rat small intestine and colon examined in vitro. |
PubMed: | Urinary excretion of phenols as an indicator of occupational exposure in the coke-plant industry. |
PubMed: | Pharmacokinetics of wood creosote: glucuronic acid and sulfate conjugation of phenolic compounds. |
PubMed: | The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended pi-conjugation dramatically stabilizes the quinone methide formed from eugenol. |
PubMed: | o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. |
PubMed: | Xylosylation of Phenolic Hydroxyl Groups of the Monomeric Lignin Model Compounds 4-Methylguaiacol and Vanillyl Alcohol by Coriolus versicolor. |
PubMed: | Suppression of intestinal smooth muscle contraction by phenolic compounds. |
PubMed: | Enzymic oxidation of capsaicin. |
PubMed: | Application of the MTT colorimetric assay to measure cytotoxic effects of phenolic compounds on established rat dental pulp cells. |
PubMed: | Analysis of beechwood creosote by gas chromatography-mass spectrometry and high-performance liquid chromatography. |
PubMed: | Nuclear magnetic resonance studies on the spatial relationship of aromatic donor molecules to the heme iron of horseradish peroxidase. |
PubMed: | [Suicide by schizophrenic patients in psychiatric hospitals]. |
PubMed: | [Cresol burns in the eye (author's transl)]. |
PubMed: | The cell envelope of the Legionnaires' disease bacterium. Morphologic and biochemical characteristics. |
PubMed: | The metabolism of vanillin and isovanillin in the rat. |
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