ABSTRACT
Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitis riparia grapes, in Vitis vinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O-ï¢-d-glucoside and MeSA 2-O-ï¢-d-xylopyranosyl (1-6) ï¢-d-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O-ï¡-l-arabinopyranosyl (1-6)-ï¢-d-glucopyranoside (violutoside) and MeSA 2-O-ï¢-d-apiofuranosyl (1-6)-ï¢-d-glucopyranoside (canthoside A), MeSA 2-O-ï¢-d-glucopyranosyl (1-6)-O-ï¢-d-glucopyranoside (gentiobioside) and MeSA 2-O-ï¡-l-rhamnopyranosyl (1-6)-ï¢-d-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456-9796 ïg/L and 5.5-143 ïg/L, respectively, while in the other wines the bound and free MeSA was below 363 ïg/L and 12 ïg/L, respectively. As this compound's olfactory threshold is between 50 and 100 ïg/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.
Subject(s)
Glycosides/chemistry , Salicylates/chemistry , Vitis/chemistry , Wine/analysis , Chromatography, Liquid , Disaccharides/chemistry , Disaccharides/isolation & purification , Glycosides/classification , Glycosides/isolation & purification , Humans , Plant Extracts/chemistry , Plant Leaves/chemistry , Salicylates/classification , Salicylates/isolation & purificationABSTRACT
Regulatory agencies are charged with addressing the endocrine disrupting potential of large numbers of chemicals for which there is often little or no data on which to make decisions. Prioritizing the chemicals of greatest concern for further screening for potential hazard to humans and wildlife is an initial step in the process. This paper presents the collection of in vitro data using assays optimized to detect low affinity estrogen receptor (ER) binding chemicals and the use of that data to build effects-based chemical categories following QSAR approaches and principles pioneered by Gilman Veith and colleagues for application to environmental regulatory challenges. Effects-based chemical categories were built using these QSAR principles focused on the types of chemicals in the specific regulatory domain of concern, i.e. non-steroidal industrial chemicals, and based upon a mechanistic hypothesis of how these non-steroidal chemicals of seemingly dissimilar structure to 17ß-estradiol (E2) could interact with the ER via two distinct binding types. Chemicals were also tested to solubility thereby minimizing false negatives and providing confidence in determination of chemicals as inactive. The high-quality data collected in this manner were used to build an ER expert system for chemical prioritization described in a companion article in this journal.
Subject(s)
Estrogens/classification , Animals , Endocrine Disruptors/chemistry , Endocrine Disruptors/classification , Endocrine Disruptors/toxicity , Estrogens/toxicity , Parabens/chemistry , Parabens/classification , Parabens/toxicity , Phenols/chemistry , Phenols/classification , Phenols/toxicity , Quantitative Structure-Activity Relationship , Receptors, Estrogen/metabolism , Salicylates/chemistry , Salicylates/classification , Salicylates/toxicity , TroutABSTRACT
A toxicologic and dermatologic review of methyl 4-methylsalicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Administration, Cutaneous , Animals , Consumer Product Safety , Humans , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/metabolism , Skin AbsorptionABSTRACT
A toxicologic and dermatologic review of hexyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Allergens/classification , Allergens/pharmacokinetics , Allergens/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of benzyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Allergens/classification , Allergens/pharmacokinetics , Allergens/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Mutagenicity Tests , Mutagens/classification , Mutagens/pharmacokinetics , Mutagens/toxicity , Perfume/classification , Perfume/pharmacokinetics , Photosensitizing Agents/classification , Photosensitizing Agents/pharmacokinetics , Photosensitizing Agents/toxicity , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin Irritancy Tests , Skin TestsABSTRACT
A toxicologic and dermatologic review of cis-3-hexenyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Allergens/classification , Allergens/pharmacokinetics , Allergens/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Stereoisomerism , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of butyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , In Vitro Techniques , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
An evaluation and review of a structurally related group of fragrance materials.
Subject(s)
Cyclooxygenase Inhibitors/toxicity , Noxae/toxicity , Perfume/toxicity , Salicylates/toxicity , Skin/drug effects , Allergens/classification , Allergens/pharmacokinetics , Allergens/toxicity , Animals , Consumer Product Safety , Cyclooxygenase Inhibitors/classification , Cyclooxygenase Inhibitors/pharmacokinetics , Dose-Response Relationship, Drug , Expert Testimony , Humans , Noxae/classification , Noxae/pharmacokinetics , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/metabolism , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of 1,3-dimethyl-3-butenyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Butanes/toxicity , Perfume/toxicity , Salicylates/toxicity , Animals , Butanes/classification , Butanes/pharmacokinetics , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Tests , Toxicity TestsABSTRACT
A toxicological and dermatological review of ethyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of pentyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of phenethyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Allergens/classification , Allergens/pharmacokinetics , Allergens/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of trans-2-hexenyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/pharmacokinetics , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Stereoisomerism , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of phenyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Mutagens/classification , Mutagens/pharmacokinetics , Mutagens/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin Absorption , Skin Irritancy Tests , Skin Tests , Teratogens/classification , Teratogens/pharmacokinetics , Teratogens/toxicity , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of ethyl hexyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Humans , In Vitro Techniques , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of 3-methyl-2-butenyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Butanes/toxicity , Perfume/toxicity , Salicylates/toxicity , Animals , Butanes/classification , Butanes/pharmacokinetics , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of methyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Noxae/toxicity , Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , In Vitro Techniques , Noxae/classification , Noxae/pharmacokinetics , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of p-cresyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Cresols/toxicity , Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Cresols/classification , Cresols/pharmacokinetics , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
A toxicologic and dermatologic review of isobutyl salicylate when used as a fragrance ingredient is presented.
Subject(s)
Perfume/toxicity , Salicylates/toxicity , Animals , Consumer Product Safety , Dose-Response Relationship, Drug , Humans , Irritants/classification , Irritants/pharmacokinetics , Irritants/toxicity , Perfume/classification , Perfume/pharmacokinetics , Risk Assessment , Salicylates/classification , Salicylates/pharmacokinetics , Skin/drug effects , Skin/metabolism , Skin/pathology , Skin Absorption , Skin Irritancy Tests , Skin Tests , Toxicity TestsABSTRACT
Methyl salicylate is a compound currently used in the creation of many flavors. It can be obtained by synthesis or from two natural sources: essential oil of wintergreen and essential oil of sweet birch bark. Deuterium site-specific natural isotope abundance (A(i)) determination by NMR spectroscopy with the method of reference ERETIC ((2)H-ERETIC-NMR) has been applied to this compound. A(i) measurements have been performed on 19 samples of methyl salicylate from different origins, natural/synthetic and commercial/extracted. This study demonstrates that appropriate treatment performed on the data allows discrimination between synthetic and natural samples. Moreover, the representation of intramolecular ratios R(6/5) as a function of R(3/2) distinguishes between synthetics, wintergreen oils, and sweet birch bark oils.
