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Chemical Compound Review

Analgit     methyl 2-hydroxybenzoate

Synonyms: Exagien, Flucarmit, Betula, Panalgesic, Theragesic, ...
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Disease relevance of Synthetic Wintergreen Oil

  • Pollen of the white birch (Betula verrucosa) is one of the main causes of Type I allergic reactions (allergic rhinoconjunctivitis, allergic bronchial asthma) in Middle and Northern Europe, North America and the USSR [1].
  • METHODS: Forty-nine patients with histories of birch pollen allergy from the upper and lower airways, positive skin prick test and conjunctival provocation test results, and in vitro specific IgE to birch pollen (Betula verrucosa ) extract were included [2].
  • On the other hand, anti-paclitaxel IgG were above all detected in sera of subjects displaying hypersensitivity reactions during the pollination periods of Taxus sp. and Betula sp. This natural anti-paclitaxel IgG acquisition by individuals living in the distribution areas of these trees could be at the origin of atopic manifestations [3].
  • The fate of an introduced mer/luc-tagged antagonistic Pseudomonas fluorescens 31K3 was monitored in the rhizosphere of silver birch (Betula pendula) seedlings grown in microcosms containing forest humus or nursery peat [4].
  • The effects of Agrobacterium pRiA4 rol and aux genes, controlled by their endogenous promoters, on tree growth and wood anatomy and chemistry were studied in 5- and 7-year-old silver birch (Betula pendula Roth) plants [5].

Psychiatry related information on Synthetic Wintergreen Oil


High impact information on Synthetic Wintergreen Oil

  • A complementary DNA encoding a pollen allergen from white birch (Betula verrucosa) that was isolated from a pollen complementary DNA library with serum immunoglobulin E from a birch pollen-allergic individual revealed significant sequence homology to profilins [7].
  • Here we demonstrate that soluble factors from birch (Betula alba L.) pollen activate human dendritic cells (DCs) as documented by phenotypical and functional maturation and altered cytokine production [8].
  • We show that, in addition to noxious cold, pungent natural compounds present in cinnamon oil, wintergreen oil, clove oil, mustard oil, and ginger all activate TRPA1 (ANKTM1) [9].
  • The three-dimensional structure of the major birch pollen allergen, the 17,500 M(r) acidic protein Bet v 1 (from the birch, Betula verrucosa), is presented as determined both in the crystalline state by X-ray diffraction and in solution by nuclear magnetic resonance (NMR) spectroscopy [10].
  • Fine-resolution analysis of the lifetime leaf record of an individual birch (Betula pendula) indicates a gradual reduction of stomatal frequency as a phenotypic acclimation to CO2 increase [11].

Chemical compound and disease context of Synthetic Wintergreen Oil


Biological context of Synthetic Wintergreen Oil

  • WT Betula papyrifera (Marsh) was included to compare the senescence performance of a species that does not produce anthocyanins in autumn [13].
  • In all families, evidence for linkage of skin test reactivity for Betula, Lolium, and Artemisia was strongest in a region on chromosome 21 that contained the candidate gene, A Disintegrin And Metalloprotease domain 33 (ADAM33) [14].
  • The global pattern of gene expression during these stages in the birch (Betula pendula)-Paxillus involutus ECM association was analyzed using cDNA microarrays [15].
  • We have isolated by DDRT-PCR (differential-display reverse-transcription polymerase chain reaction) and cDNA library screening a 1.3 kb cDNA corresponding to a strongly ozone-inducible transcript from birch (Betula pendula Roth) [16].
  • We studied the effects of elevated concentrations of carbon dioxide ([CO2]) and ozone ([O3]) on growth, biomass allocation and leaf area of field-grown O3-tolerant (Clone 4) and O3-sensitive clones (Clone 80) of European silver birch (Betula pendula Roth) trees during 1999-2001 [17].

Anatomical context of Synthetic Wintergreen Oil

  • In birch (Betula pubescens) these events are triggered by short photoperiod, and involve the production of 1,3-beta-D-glucan containing sphincters on the plasmodesmata [18].
  • The outermost phellems of Abies alba Mill., Acer pseudoplatanus L., Aesculus hippocastanum L., Betula potaninii L.C. Hue and Sambucus nigra L. have been isolated enzymatically, resulting in membranes with five to seven heavily suberized cork cell layers [19].
  • Some groups of peptides representing T cell epitopes (Betula verrucosa; Bet VI peptides, p7-33, p23-46, p138-160) appeared to be shared by the majority, while another peptide (Bet VI p72-95) was recognized predominantly by patients who expressed HLA-DR9 and/or HLA-DQ3 molecules [20].
  • A specific condensed lignin substructure, dibenzodioxocin, was immunolocalized in differentiating cell walls of Norway spruce ( Picea abies (L.) H. Karsten) and silver birch ( Betula pendula Roth) xylem [21].
  • The best agreement was observed with Phleum pratense, egg white, corn, Betula verrucosa and cat epithelium [22].

Associations of Synthetic Wintergreen Oil with other chemical compounds

  • HPLC analysis of APEs from Phleum pratense and Betula alba pollen demonstrated the occurrence of linoleic and alpha-linolenic acid as well as their monohydroxylated derivatives [23].
  • The phenols in beech (Fagus sylvatica), birch (Betula pendula) and ash (Fraxinus excelsior) wood dusts were compared using a mass spectrometer fitted with an electrospray ionisation interface with liquid chromatographic separation [24].
  • We tested our hypothesis at the free-air CO(2) and O(3) enrichment (FACE) experiment at Rhinelander, Wisconsin, in which Populus tremuloides, Betula papyrifera, and Acer saccharum were grown under factorial CO(2) and O(3) treatments [25].
  • During the first treatment year, the patients received double-blinded IT with either birch (Betula verrucosa) or grass (Phleum pratense) pollen extracts adsorbed to aluminum hydroxide [26].
  • Japanese white birch (Betula platyphylla var. japonica) leaves that developed wholly during a period of drought showed an increase in leaf nitrogen and a decrease in leaf carbohydrates that could ameliorate photosynthetic down-regulation, defined as a decrease in V(cmax) in response to elevated [CO(2)] [27].

Gene context of Synthetic Wintergreen Oil

  • Indeed, known sensitizers such as PPD and 2-MBT significantly augmented CD54 and CD86 expression in a dose-dependent manner while non-sensitizers, such as SLS and methyl salicylate (MS), did not [28].
  • The aim of this study was to examine the association between mild head injury, APOE and dementia.Methods: Data were obtained from the Betula prospective population-based study of aging, memory, and health [29].
  • Allergens with homology to the major birch ( Betula verrucosa ) pollen allergen, Bet v 1, belong to the most potent elicitors of IgE-mediated allergies [30].
  • Males of the green-veined butterfly Pieris napi synthesize and transfer the volatile methyl salicylate (MeS) to females at mating, a substance that is emitted by non-virgin females when courted by males, curtailing courtship and decreasing the likelihood of female re-mating [31].
  • Characterization of a birch (Betula pendula Roth.) embryogenic gene, BP8 [32].

Analytical, diagnostic and therapeutic context of Synthetic Wintergreen Oil

  • Based on data from a prospective cohort study (Betula) in our own laboratory, we have assessed and examined associations between three different forms of ApoE and performance on episodic memory tests [33].
  • METHODS: Aqueous and lipid extracts from Phleum pratense L and Betula alba L pollen were analyzed by means of HPLC [34].
  • METHODS: Mountain birch (Betula pubescens ssp. czerepanovii (Orl.) Hämet-Ahti) pollen was studied using SDS-PAGE and IgE-immunoblotting [35].
  • OBJECTIVE : The aim of this study was to compare natural birch pollen extract (BPE) and recombinant Betula verrucosa (rBet v 1) for their diagnostic value comparing skin prick tests (SPTS) and nasal provocation tests (NPTS) with specific IgE in the serum [36].
  • METHODS: The binding affinity of purified serum IgG1, IgG4 and IgE to the major allergen in birch (Betula verrucosa) pollen, Bet v 1, was analysed by surface plasmon resonance [37].


  1. The gene coding for the major birch pollen allergen Betv1, is highly homologous to a pea disease resistance response gene. Breiteneder, H., Pettenburger, K., Bito, A., Valenta, R., Kraft, D., Rumpold, H., Scheiner, O., Breitenbach, M. EMBO J. (1989) [Pubmed]
  2. Effect of 2-year placebo-controlled immunotherapy on airway symptoms and medication in patients with birch pollen allergy. Arvidsson, M.B., Löwhagen, O., Rak, S. J. Allergy Clin. Immunol. (2002) [Pubmed]
  3. Taxanes in Taxus baccata pollen: cardiotoxicity and/or allergenicity? Vanhaelen, M., Duchateau, J., Vanhaelen-Fastré, R., Jaziri, M. Planta Med. (2002) [Pubmed]
  4. Maintenance and impacts of an inoculated mer/luc-tagged Pseudomonas fluorescens on microbial communities in birch rhizospheres developed on humus and peat. Björklöf, K., Sen, R., Jørgensen, K.S. Microb. Ecol. (2003) [Pubmed]
  5. Silver birch (Betula pendula) plants with aux and rol genes show consistent changes in morphology, xylem structure and chemistry. Piispanen, R., Aronen, T., Chen, X., Saranpää, P., Häggman, H. Tree Physiol. (2003) [Pubmed]
  6. Candy flavoring as a source of salicylate poisoning. Howrie, D.L., Moriarty, R., Breit, R. Pediatrics (1985) [Pubmed]
  7. Identification of profilin as a novel pollen allergen; IgE autoreactivity in sensitized individuals. Valenta, R., Duchêne, M., Pettenburger, K., Sillaber, C., Valent, P., Bettelheim, P., Breitenbach, M., Rumpold, H., Kraft, D., Scheiner, O. Science (1991) [Pubmed]
  8. Pollen-associated phytoprostanes inhibit dendritic cell interleukin-12 production and augment T helper type 2 cell polarization. Traidl-Hoffmann, C., Mariani, V., Hochrein, H., Karg, K., Wagner, H., Ring, J., Mueller, M.J., Jakob, T., Behrendt, H. J. Exp. Med. (2005) [Pubmed]
  9. Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Bandell, M., Story, G.M., Hwang, S.W., Viswanath, V., Eid, S.R., Petrus, M.J., Earley, T.J., Patapoutian, A. Neuron (2004) [Pubmed]
  10. X-ray and NMR structure of Bet v 1, the origin of birch pollen allergy. Gajhede, M., Osmark, P., Poulsen, F.M., Ipsen, H., Larsen, J.N., Joost van Neerven, R.J., Schou, C., Løwenstein, H., Spangfort, M.D. Nat. Struct. Biol. (1996) [Pubmed]
  11. A natural experiment on plant acclimation: lifetime stomatal frequency response of an individual tree to annual atmospheric CO2 increase. Wagner, F., Below, R., Klerk, P.D., Dilcher, D.L., Joosten, H., Kürschner, W.M., Visscher, H. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  12. Manganese toxicity as indicated by visible foliar symptoms of Japanese white birch (Betula platyphylla var. japonica). Kitao, M., Lei, T.T., Nakamura, T., Koike, T. Environ. Pollut. (2001) [Pubmed]
  13. Resorption protection. Anthocyanins facilitate nutrient recovery in autumn by shielding leaves from potentially damaging light levels. Hoch, W.A., Singsaas, E.L., McCown, B.H. Plant Physiol. (2003) [Pubmed]
  14. A genome-wide search for quantitative trait loci contributing to variation in seasonal pollen reactivity. Blumenthal, M.N., Langefeld, C.D., Barnes, K.C., Ober, C., Meyers, D.A., King, R.A., Beaty, T.H., Beck, S.R., Bleecker, E.R., Rich, S.S. J. Allergy Clin. Immunol. (2006) [Pubmed]
  15. Global patterns of gene regulation associated with the development of ectomycorrhiza between birch (Betula pendula Roth.) and Paxillus involutus (Batsch) Fr. Le Quéré, A., Wright, D.P., Söderström, B., Tunlid, A., Johansson, T. Mol. Plant Microbe Interact. (2005) [Pubmed]
  16. Isolation and characterization of cDNA for a plant mitochondrial phosphate translocator (Mpt1): ozone stress induces Mpt1 mRNA accumulation in birch (Betula pendula Roth). Kiiskinen, M., Korhonen, M., Kangasjärvi, J. Plant Mol. Biol. (1997) [Pubmed]
  17. Silver birch and climate change: variable growth and carbon allocation responses to elevated concentrations of carbon dioxide and ozone. Riikonen, J., Lindsberg, M.M., Holopainen, T., Oksanen, E., Lappi, J., Peltonen, P., Vapaavuori, E. Tree Physiol. (2004) [Pubmed]
  18. The shoot apical meristem restores its symplasmic organization during chilling-induced release from dormancy. Rinne, P.L., Kaikuranta, P.M., van der Schoot, C. Plant J. (2001) [Pubmed]
  19. Water and oxygen permeance of phellems isolated from trees: the role of waxes and lenticels. Groh, B., Hübner, C., Lendzian, K.J. Planta (2002) [Pubmed]
  20. Epitope analysis of birch pollen allergen in Japanese subjects. Abe, Y., Kimura, S., Kokubo, T., Mizumoto, K., Uehara, M., Katagiri, M. J. Clin. Immunol. (1997) [Pubmed]
  21. The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem. Kukkola, E.M., Koutaniemi, S., Pöllänen, E., Gustafsson, M., Karhunen, P., Lundell, T.K., Saranpää, P., Kilpeläinen, I., Teeri, T.H., Fagerstedt, K.V. Planta (2004) [Pubmed]
  22. Comparative evaluation of RAST and FAST for 11 allergens in 288 patients. Gueant, J.L., Moneret-Vautrin, D.A., Dejardin, G., Algalarondo, C., Nicolas, J.P., Grilliat, J.P. Allergy (1989) [Pubmed]
  23. Chemotaxis and activation of human peripheral blood eosinophils induced by pollen-associated lipid mediators. Plötz, S.G., Traidl-Hoffmann, C., Feussner, I., Kasche, A., Feser, A., Ring, J., Jakob, T., Behrendt, H. J. Allergy Clin. Immunol. (2004) [Pubmed]
  24. Phenolics in selected European hardwood species by liquid chromatography-electrospray ionisation mass spectrometry. Mämmelä, P. The Analyst. (2001) [Pubmed]
  25. Fungal community composition and metabolism under elevated CO(2) and O(3). Chung, H., Zak, D.R., Lilleskov, E.A. Oecologia (2006) [Pubmed]
  26. Allergen-specific immunotherapy in birch- and grass-pollen-allergic rhinitis. II. Side-effects. Winther, L., Malling, H.J., Mosbech, H. Allergy (2000) [Pubmed]
  27. Interaction of drought and elevated CO(2 )concentration on photosynthetic down-regulation and susceptibility to photoinhibition in Japanese white birch seedlings grown with limited N availability. Kitao, M., Lei, T.T., Koike, T., Kayama, M., Tobita, H., Maruyama, Y. Tree Physiol. (2007) [Pubmed]
  28. Evaluation of the skin sensitization potential of chemicals using expression of co-stimulatory molecules, CD54 and CD86, on the naive THP-1 cell line. Yoshida, Y., Sakaguchi, H., Ito, Y., Okuda, M., Suzuki, H. Toxicology in vitro : an international journal published in association with BIBRA. (2003) [Pubmed]
  29. Increased risk of dementia following mild head injury for carriers but not for non-carriers of the APOE epsilon4 allele. Sundstr??m, A., Nilsson, L.G., Cruts, M., Adolfsson, R., Van Broeckhoven, C., Nyberg, L. International psychogeriatrics / IPA (2007) [Pubmed]
  30. Molecular characterization of recombinant T1, a non-allergenic periwinkle (Catharanthus roseus) protein, with sequence similarity to the Bet v 1 plant allergen family. Laffer, S., Hamdi, S., Lupinek, C., Sperr, W.R., Valent, P., Verdino, P., Keller, W., Grote, M., Hoffmann-Sommergruber, K., Scheiner, O., Kraft, D., Rideau, M., Valenta, R. Biochem. J. (2003) [Pubmed]
  31. Sexual conflict and anti-aphrodisiac titre in a polyandrous butterfly: male ejaculate tailoring and absence of female control. Andersson, J., Borg-Karlson, A.K., Wiklund, C. Proc. Biol. Sci. (2004) [Pubmed]
  32. Characterization of a birch (Betula pendula Roth.) embryogenic gene, BP8. Puupponen-Pimiä, R., Saloheimo, M., Vasara, T., Ra, R., Gaugecz, J., Kurtén, U., Knowles, J.K., Keränen, S., Kauppinen, V. Plant Mol. Biol. (1993) [Pubmed]
  33. Genetic variation in memory functioning. Nilsson, L.G., Nyberg, L., Bäckman, L. Neuroscience and biobehavioral reviews. (2002) [Pubmed]
  34. Lipid mediators from pollen act as chemoattractants and activators of polymorphonuclear granulocytes. Traidl-Hoffmann, C., Kasche, A., Jakob, T., Huger, M., Plötz, S., Feussner, I., Ring, J., Behrendt, H. J. Allergy Clin. Immunol. (2002) [Pubmed]
  35. Genetic and environmental factors affecting the allergenicity of birch (Betula pubescens ssp. czerepanovii [Orl.] Hämet-ahti) pollen. Ahlholm, J.U., Helander, M.L., Savolainen, J. Clin. Exp. Allergy (1998) [Pubmed]
  36. In vitro and in vivo allergenicity of recombinant Bet v 1 compared to the reactivity of natural birch pollen extract. Tresch, S., Holzmann, D., Baumann, S., Blaser, K., Wüthrich, B., Crameri, R., Schmid-Grendelmeier, P. Clin. Exp. Allergy (2003) [Pubmed]
  37. Vaccination for birch pollen allergy: comparison of the affinities of specific immunoglobulins E, G1 and G4 measured by surface plasmon resonance. Jakobsen, C.G., Bodtger, U., Poulsen, L.K., Roggen, E.L. Clin. Exp. Allergy (2005) [Pubmed]
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