safrole

Summary

Summary: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).

Top Publications

  1. Su L, Zhao B, Lv X, Wang N, Zhao J, Zhang S, et al. Safrole oxide induces neuronal apoptosis through inhibition of integrin beta4/SOD activity and elevation of ROS/NADPH oxidase activity. Life Sci. 2007;80:999-1006 pubmed
    ..We have previously shown that safrole oxide, a small molecule, induces integrin beta4 expression and promotes apoptosis in vascular endothelial cells...
  2. Wang D, Wang X, Xia X. [Analysis of season variation of methyleugenol and safrole in Asarum heterotropoides by gas chromatography]. Se Pu. 1997;15:85-6 pubmed
    We established a method for quantitative analysis of methyleugenol and safrole in Asarum heterotropoides by GC to study their season variation...
  3. Reynertson K, Balick M, Lee R, Raynor W, Pelep Y, Kennelly E. A traditional method of Cinnamomum carolinense preparation eliminates safrole from a therapeutic Pohnpean tea. J Ethnopharmacol. 2005;102:269-74 pubmed
    ..Many species of Cinnamomum contain the known hepatocarcinogen safrole, sparking concern regarding habitual consumption of this beverage...
  4. Liu T, Chung Y, Wang P, Chi C, Hsieh L. Safrole-DNA adducts in human peripheral blood--an association with areca quid chewing and CYP2E1 polymorphisms. Mutat Res. 2004;559:59-66 pubmed
    It has been recently demonstrated that safrole (4-allyl-1,2-methylenedioxybenzene)-DNA adducts are present in oral cancer tissue from patients who have chewed areca quid (AQ) containing high concentration of safrole...
  5. Ni W, Tsai C, Yang S, Chang Y. Elevated expression of NF-kappaB in oral submucous fibrosis--evidence for NF-kappaB induction by safrole in human buccal mucosal fibroblasts. Oral Oncol. 2007;43:557-62 pubmed
    ..Primary human buccal mucosal fibroblasts (BMFs) were established and challenged with safrole, a major polyphenolic compound in the influorescence of Piper betel, by cytotoxicity and western blot assays...
  6. Chang M, Ko C, Lin R, Hsieh L. Biological monitoring of environment exposure to safrole and the Taiwanese betel quid chewing. Arch Environ Contam Toxicol. 2002;43:432-7 pubmed
    A rapid and sensitive biological monitoring (BM) method for assessing exposure to the environmental carcinogen safrole has been developed...
  7. Beyer J, Ehlers D, Maurer H. Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Ther Drug Monit. 2006;28:568-75 pubmed
    ..formation of amphetamine derivatives from the main nutmeg ingredients elemicin (EL), myristicin (MY), and safrole (SA)...
  8. Su L, Zhang H, Zhao J, Zhang S, Zhang Y, Zhao B, et al. Safrole-2',3'-oxide induces atherosclerotic plaque vulnerability in apolipoprotein E-knockout mice. Toxicol Lett. 2013;217:129-36 pubmed publisher
    b>Safrole-2',3'-oxide (SFO) is the major electrophilic metabolite of safrole (4-allyl-1, 2-methylenedioxybenzene), a natural plant constituent found in essential oils of numerous edible herbs and spices and in food containing these herbs, ..
  9. Luo G, Qato M, Guenthner T. Hydrolysis of the 2',3'-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metab Dispos. 1992;20:440-5 pubmed
    2',3'-Allylic epoxide derivatives of allylbenzene and its analogs estragole, eugenol, and safrole were synthesized, and their enzymatic conversion to dihydrodiols by cytosolic and microsomal epoxide hydrolases was examined...

More Information

Publications62

  1. Yu F, Yang J, Yu C, Chiang J, Lu C, Chung H, et al. Safrole suppresses murine myelomonocytic leukemia WEHI-3 cells in vivo, and stimulates macrophage phagocytosis and natural killer cell cytotoxicity in leukemic mice. Environ Toxicol. 2013;28:601-8 pubmed publisher
    ..However, some phytochemicals have mutagenic effects. Safrole, a component of Piper betle inflorescence, has been reported to be a carcinogen...
  2. Yu F, Yang J, Yu C, Lu C, Chiang J, Lin C, et al. Safrole induces apoptosis in human oral cancer HSC-3 cells. J Dent Res. 2011;90:168-74 pubmed publisher
    ..However, there are data suggesting a mutagenic effect of some phytochemicals. We hypothesized that safrole would have anticancer effects on human oral squamous cell carcinoma HSC-3 cells...
  3. Shieh D, Chiang L, Shieh T. Augmented mRNA expression of tissue inhibitor of metalloproteinase-1 in buccal mucosal fibroblasts by arecoline and safrole as a possible pathogenesis for oral submucous fibrosis. Oral Oncol. 2003;39:728-35 pubmed
    ..The present study used arecoline, arecaidine and safrole, which are thought to be major toxic ingredients in BQ, as candidates to explore the role of TIMP-1 expression in ..
  4. Niyama E, Brito H, Cremona M, Teotonio E, Reyes R, Brito G, et al. Synthesis and spectroscopic behavior of highly luminescent Eu(3+)-dibenzoylmethanate (DBM) complexes with sulfoxide ligands. Spectrochim Acta A Mol Biomol Spectrosc. 2005;61:2643-9 pubmed
    ..The pure red emission of the Eu-complexes has been confirmed by (x, y) color coordinates. ..
  5. Abramovitch A, Fensterbank L, Malacria M, Marek I. Convergent preparation of enantiomerically pure polyalkylated cyclopropane derivatives. Angew Chem Int Ed Engl. 2008;47:6865-8 pubmed publisher
  6. Kao A, Chiu C, Vellucci D, Yang Y, Patel V, Guan S, et al. Development of a novel cross-linking strategy for fast and accurate identification of cross-linked peptides of protein complexes. Mol Cell Proteomics. 2011;10:M110.002212 pubmed publisher
    ..Given its effectiveness and simplicity, this cross-linking strategy can find a broad range of applications in elucidating the structural topology of proteins and protein complexes. ..
  7. Hanigan M, Winkler M, Drinkwater N. Induction of three histochemically distinct populations of hepatic foci in C57BL/6J mice. Carcinogenesis. 1993;14:1035-40 pubmed
    ..However, several carcinogens, including safrole and ortho-azoaminotoluene (OAT), have been reported to induce GGT-positive foci in mice...
  8. Miao J, Zhao B, Li H, Zhang S, Du C. Effect of safrole oxide on vascular endothelial cell growth and apoptosis induced by deprivation of fibroblast growth factor. Acta Pharmacol Sin. 2002;23:323-6 pubmed
    To investigate effect of safrole oxide on cell growth and apoptosis induced by deprivation of survival factors (fibroblast growth factors, aFGF and bFGF) in vascular endothelial cells (VEC)...
  9. Su L, Zhao J, Zhao B, Zhang S, Miao J. Safrole oxide induces human umbilical vein endothelial cell transdifferentiation to 5-hydroxytryptaminergic neuron-like cells through tropomyosin receptor kinase A/cyclooxygenase 2/nuclear factor-kappa B/interleukin 8 signaling. Int J Biochem Cell Biol. 2011;43:1512-22 pubmed publisher
    ..We previously found that safrole oxide induced human umbilical vein endothelial cell transdifferentiation into neuron-like cells...
  10. Murray M. Toxicological actions of plant-derived and anthropogenic methylenedioxyphenyl-substituted chemicals in mammals and insects. J Toxicol Environ Health B Crit Rev. 2012;15:365-95 pubmed publisher
    ..Finally, although most MDP agents are well tolerated, several, typified by safrole, aristolochic acid, and MDP-kavalactones, are associated with significant toxicities, including the risk of ..
  11. Buchanan H, Daeid N, Meier Augenstein W, Kemp H, Kerr W, Middleditch M. Emerging use of isotope ratio mass spectrometry as a tool for discrimination of 3,4-methylenedioxymethamphetamine by synthetic route. Anal Chem. 2008;80:3350-6 pubmed publisher
    ..Furthermore, hierarchical cluster analysis using 2H data on its own or combined with 13C and/or 15N provides a statistical means for accurate discrimination by synthetic route. ..
  12. Leite A, da Silva K, de Souza I, de Araújo J, Brondani D. Synthesis, antitumour and antimicrobial activities of new peptidyl derivatives containing the 1,3-benzodioxole system. Eur J Med Chem. 2004;39:1059-65 pubmed
    ..The compounds that could be conveniently prepared in a few steps processes from natural safrole have been characterised by IR and 1H-NMR spectroscopy...
  13. Raffo A, D Aloise A, Magrì A, Leclercq C. Quantitation of tr-cinnamaldehyde, safrole and myristicin in cola-flavoured soft drinks to improve the assessment of their dietary exposure. Food Chem Toxicol. 2013;59:626-35 pubmed publisher
    Quantitation of tr-cinnamaldehyde, safrole and myristicin was carried out in 70 samples of cola-flavoured soft drinks purchased in eight European countries with the purpose of assessing the variability in the levels of these substances...
  14. Zhao J, Miao J, Zhao B, Zhang S. Upregulating of Fas, integrin beta4 and P53 and depressing of PC-PLC activity and ROS level in VEC apoptosis by safrole oxide. FEBS Lett. 2005;579:5809-13 pubmed
    Previously, we found that safrole oxide could trigger vascular endothelial cell (VEC) apoptosis...
  15. Kao L, Wilkinson C. Inhibition of cytochrome P-450c-mediated benzo[a]pyrene hydroxylase and ethoxyresorufin O-deethylase by dihydrosafrole. Xenobiotica. 1987;17:793-805 pubmed
    ..6. The results indicate that ethoxyresorufin and benzo[a]pyrene may occupy different binding sites on cytochrome P-450c and that dihydrosafrole binds primarily to the site utilized by ethoxyresorufin. ..
  16. Chung Y, Hsieh L, Chen I, Liao C, Liou S, Chi C, et al. Sulfotransferase 1A1 haplotypes associated with oral squamous cell carcinoma susceptibility in male Taiwanese. Carcinogenesis. 2009;30:286-94 pubmed publisher
    We have previously demonstrated that betel quid containing safrole induced DNA adducts are highly associated with the development of oral squamous cell carcinoma (OSCC) in Taiwan...
  17. Tao P, Fisher J, Shi Q, Mobashery S, Schlegel H. Matrix metalloproteinase 2 (MMP2) inhibition: DFT and QM/MM studies of the deprotonation-initialized ring-opening reaction of the sulfoxide analogue of SB-3CT. J Phys Chem B. 2010;114:1030-7 pubmed publisher
    ..This agrees well with the experiments, where SB-3CT is a more effective inhibitor of MMP2 than its sulfoxide analogue. ..
  18. Lv G, Huang W, Yang F, Li J, Li S. Pressurized liquid extraction and GC-MS analysis for simultaneous determination of seven components in Cinnamomum cassia and the effect of sample preparation. J Sep Sci. 2010;33:2341-8 pubmed publisher
    ..including cinnamaldehyde, copaene, cinnamic acid, coumarin, 2-methoxycinnamaldehyde, 2-methoxycinnamic acid and safrole in Cinnamomum cassia...
  19. Chang Y, Imasaka T. Simple pretreatment procedure combined with gas chromatography/multiphoton ionization/mass spectrometry for the analysis of dioxins in soil samples obtained after the T?hoku earthquake. Anal Chem. 2013;85:349-54 pubmed publisher
    ..This simple and rapid pretreatment procedure can be useful for monitoring the environment to prevent unexpected exposure of toxic dioxins for the workers who have to process more than 20 million tons of the wastes in a few years. ..
  20. Naito S, Nishimura M. Enantioselective uptake of BOF-4272, a xanthine oxidase inhibitor with a chiral sulfoxide, by isolated rat hepatocytes. Yakugaku Zasshi. 2001;121:989-94 pubmed
  21. Ohyama T, Nebert D, Negishi M. Isosafrole-induced cytochrome P2-450 in DBA/2N mouse liver. Characterization and genetic control of induction. J Biol Chem. 1984;259:2675-82 pubmed
  22. Baciocchi E, Del Giacco T, Gerini M, Lanzalunga O. Aryl sulfoxide radical cations. Generation, spectral properties, and theoretical calculations. J Phys Chem A. 2006;110:9940-8 pubmed
    ..The ionization energies (IE) of the 4-X ring substituted neutral aromatic sulfoxides were also calculated, which were found to satisfactorily correlate with the experimental E(p) potentials measured by cyclic voltammetry. ..
  23. Fanela T, Baldin E, Pannuti L, Cruz P, Crotti A, Takeara R, et al. Lethal and Inhibitory Activities of Plant-Derived Essential Oils Against Bemisia tabaci Gennadius (Hemiptera: Aleyrodidae) Biotype B in Tomato. Neotrop Entomol. 2016;45:201-10 pubmed publisher
    ..tabaci biotype B, respectively. The major chemical constituents of PC-EO were identified as being safrole (29.3%), α-pinene (19.2%), and β-pinene (14.3%), whereas diallyl trisulfide (66...
  24. Alcoba A, Melo D, de Andrade P, Dias H, Pagotti M, Magalhaes L, et al. Chemical composition and in vitro antileishmanial and cytotoxic activities of the essential oils of Ocotea dispersa (Nees) Mez and Ocotea odorifera (Vell) Rohwer (Lauraceae). Nat Prod Res. 2017;:1-4 pubmed publisher
    ..9%), valencene (10.2%), ?-elemene (9.3%) and isospathulenol (7.3%) are the major constituents of OD-EO, whereas safrole (36.3%), ?-cadinene (6.6%), camphor (6.5%) and ?-copaene (6.0%) are the main constituents of OO-EO...
  25. Zhao J, Miao J, Zhao B, Zhang S, Yin D. Suppressing Akt phosphorylation and activating Fas by safrole oxide inhibited angiogenesis and induced vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 and serum. Int J Biochem Cell Biol. 2006;38:1603-13 pubmed
    ..To address this question, in this study, the effects of safrole oxide on angiogenesis and VEC growth stimulated by FGF-2 were investigated...
  26. Du A, Zhao B, Miao J, Yin D, Zhang S. Safrole oxide induces apoptosis by up-regulating Fas and FasL instead of integrin beta4 in A549 human lung cancer cells. Bioorg Med Chem. 2006;14:2438-45 pubmed
    Previously, we found that 3,4-(methylenedioxy)-1-(2',3'-epoxypropyl)-benzene (safrole oxide) induced a typical apoptosis in A549 human lung cancer cells by activating caspase-3, -8, and -9...
  27. Verbrugge L, Giesy J, Verbrugge D, Woodin B, Stegeman J. Catalytic and immunochemical properties of hepatic cytochrome P450 1A in three avian species treated with beta-naphthoflavone or isosafrole. Comp Biochem Physiol C Toxicol Pharmacol. 2001;130:67-83 pubmed
    ..Variations in responses among avian species indicate that CYP1A proteins and substrate specificities should be characterized for each species used in PHAH biomonitoring programs. ..
  28. Weil M, Shum Cheong Sing A, Méot J, Boulanger R, Bohuon P. Impact of blanching, sweating and drying operations on pungency, aroma and color of Piper borbonense. Food Chem. 2017;219:274-281 pubmed publisher
    ..drying, had the largest impact on the composition of aroma, increasing para-cymene content by 89% and reducing safrole content by 33% in dried pepper compared to fresh. Blanching increased the drying rate thus reducing drying time...
  29. Du A, Zhang S, Miao J, Zhao B. Safrole oxide induces apoptosis in A549 human lung cancer cells. Exp Lung Res. 2004;30:419-29 pubmed
    3,4-(Methylenedioxy)-1-(2',3'-epoxypropyl)-benzene (safrole oxide) was synthesized in the authors' laboratory...
  30. Kitamura S, Suzuki T, Kadota T, Yoshida M, Ohashi K, Ohta S. In vitro metabolism of fenthion and fenthion sulfoxide by liver preparations of sea bream, goldfish, and rats. Drug Metab Dispos. 2003;31:179-86 pubmed
    ..Thus, fenthion and fenthion sulfoxide are interconvertible in fish and rats through the activities of cytochrome P450, flavin-containing monooxygenase, and aldehyde oxidase. ..
  31. Saitoh M, Kunitomo J, Kimura E, Yamano T, Itoh F, Kori M. Enantioselective synthesis of the novel chiral sulfoxide derivative as a glycogen synthase kinase 3beta inhibitor. Chem Pharm Bull (Tokyo). 2010;58:1252-4 pubmed
    ..We investigated practical asymmetric preparation methods for the scale-up synthesis of (S)-1. The highly enantioselective synthesis of (S)-1 (94% ee) was achieved by titanium-mediated oxidation with D-(-)-diethyl tartrate on gram scale. ..
  32. Zhao B, Du A, Miao J, Zhao K, Du C. Effects of novel safrole oxide derivatives, 1-methoxy-3-(3,4-methylenedioxyphenyl)-2-propanol and 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol, on apoptosis induced by deprivation of survival factors in vascular endothelial cells. Vascul Pharmacol. 2003;40:183-7 pubmed
    Two safrole oxide derivatives, 1-methoxy-3-(3,4-methylenedioxyphenyl)-2-propanol (MOD) and 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol (EOD), were newly synthesized as promoters of apoptosis in vascular endothelial cells (VECs)...
  33. Fan M, Lin S, Yu C, Tang N, Ho H, Chung H, et al. Safrole-modulated immune response is mediated through enhancing the CD11b surface marker and stimulating the phagocytosis by macrophages in BALB/c mice. Hum Exp Toxicol. 2012;31:898-904 pubmed
    b>Safrole, a component of piper betle inflorescence, is a documented rodent hepatocarcinogen and inhibits bactericidal activity and the release of superoxide anion (O(2-)) by polymorphonuclear leukocytes (PMNs)...
  34. Kouokam J, Zapp J, Becker H. Oxygen-containing sulfur-rich compounds from the bark of the tropical garlic tree Scorodophloeus zenkeri Harms. Phytochemistry. 2002;60:403-7 pubmed
    ..The structures were determined by spectral methods, essentially MS and NMR experiments. ..
  35. Leroux F, Berthelot A, Bonnafoux L, Panossian A, Colobert F. Transition-metal-free atropo-selective synthesis of biaryl compounds based on arynes. Chemistry. 2012;18:14232-6 pubmed publisher
    ..A modular way towards biaryls: Highly enantioenriched biphenyls can be prepared based on a transition-metal-free aryl-aryl coupling followed by efficient desymmetrization or deracemization and chemoselective functionalization (see scheme). ..
  36. Lavado R, Aparicio Fabre R, Schlenk D. Effects of salinity acclimation on the pesticide-metabolizing enzyme flavin-containing monooxygenase (FMO) in rainbow trout (Oncorhynchus mykiss). Comp Biochem Physiol C Toxicol Pharmacol. 2013;157:9-15 pubmed publisher
  37. Ueng Y, Hsieh C, Don M, Chi C, Ho L. Identification of the main human cytochrome P450 enzymes involved in safrole 1'-hydroxylation. Chem Res Toxicol. 2004;17:1151-6 pubmed
    b>Safrole is a natural plant constituent, found in sassafras oil and certain other essential oils...
  38. Muchtaridi -, Subarnas A, Apriyantono A, Mustarichie R. Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. Int J Mol Sci. 2010;11:4771-81 pubmed publisher
    ..2 ?g/mL and 7.1 ?g/mL, respectively. Other essential oil compounds identified in plasma were safrole (two-hour inhalation: 1.28 ?g/mL), 4-terpineol (half-hour inhalation: 1.49 ?g/mL, one-hour inhalation: 2...
  39. Fernández de la Pradilla R, Colomer I, Viso A. Sulfinyl-mediated stereoselective Overman rearrangements and Diels-Alder cycloadditions. Org Lett. 2012;14:3068-71 pubmed publisher
    ..Bis-allylic substrates lead to amido 2-sulfinyl butadiene derivatives in excellent yields, with total chemo- and diastereoselectivity. The Diels-Alder cycloaddition of related dienes is controlled by the sulfoxide moiety. ..
  40. Korang J, Grither W, McCulla R. Comparison of experimental and computationally predicted sulfoxide bond dissociation enthalpies. J Phys Chem A. 2011;115:2859-65 pubmed publisher
    ..However, the S-O BDE of divinyl sulfoxide was overestimated by this method. ..
  41. Dakas P, Jogireddy R, Valot G, Barluenga S, Winssinger N. Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin. Chemistry. 2009;15:11490-7 pubmed publisher
    ..Herein, we present our efforts on accessing macrocycles bearing an alkane, alkene, or epoxide at the benzylic position from a common benzylic sulfide intermediate to access L-783277, LL-Z1640-2, and hypothemycin. ..
  42. Taras Valéro D, Perin Roussel O, Plessis M, Perin F. Inhibition of 5,9-dimethyldibenzo[c,g]carbazole-DNA adduct formation in mouse liver by pretreatment with cytochrome P4501A inducers in vivo. Environ Mol Mutagen. 1998;32:314-24 pubmed
  43. Du A, Zhao B, Yin D, Zhang S, Miao J. Safrole oxide induces apoptosis by activating caspase-3, -8, and -9 in A549 human lung cancer cells. Bioorg Med Chem Lett. 2006;16:81-3 pubmed
    Previously we found that 3,4-(methylenedioxy)-1-(2',3'-epoxypropyl)-benzene (safrole oxide) induced a typical apoptosis in A549 human lung cancer cells...
  44. Carvalho V, Ferreira T, de Arantes A, Noël F, Tesch R, Sant Anna C, et al. LASSBio-897 Reduces Lung Injury Induced by Silica Particles in Mice: Potential Interaction with the A2A Receptor. Front Pharmacol. 2017;8:778 pubmed publisher
    ..Among a small series of N-acylhydrazones, the safrole-derived compound LASSBio-897 (3-thienylidene-3, 4-methylenedioxybenzoylhydrazide) raised interest due to its ..
  45. Nguyen H, Chen Y, Duron S, Gin D. Sulfide-mediated dehydrative glycosylation. J Am Chem Soc. 2001;123:8766-72 pubmed
    ..This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant. ..
  46. Hung S, Chen Y, Chen Y. Effects of safrole on the defensive functions of human neutrophils. J Periodontal Res. 2003;38:130-4 pubmed
    The effects of safrole on the defensive functions of human neutrophils were examined...
  47. Tharmapathy P, Fukami M, Holmsen H. The stimulatory effects of cationic amphiphilic drugs on human platelets treated with thrombin. Biochem Pharmacol. 2000;60:1267-77 pubmed
    ..g. an increase in membrane fluidity such as is known to be caused by amphipathic agents, may be in part responsible for the observed overlapping psychotropic effects of tricyclic antidepressants and phenothiazines. ..
  48. Allis J, Anderson B, Zhao G, Ross T, Pegram R. Evidence for the involvement of CYP1A2 in the metabolism of bromodichloromethane in rat liver. Toxicology. 2002;176:25-37 pubmed
    ..These results demonstrate that CYP1A2 does metabolize BDCM and does contribute to hepatotoxicity under certain conditions. ..
  49. Pino V, Lantz A, Anderson J, Berthod A, Armstrong D. Theory and use of the pseudophase model in gas-liquid chromatographic enantiomeric separations. Anal Chem. 2006;78:113-9 pubmed
    ..The three-phase model may be applied to any gas-liquid chromatography stationary phase involving a pseudophase. ..
  50. Boebel T, Gin D. Probing the mechanism of sulfoxide-catalyzed hemiacetal activation in dehydrative glycosylation. J Org Chem. 2005;70:5818-26 pubmed
    ..Further confirmation was obtained through the independent synthesis, structure verification, and (1)H NMR detection of glycosyl oxosulfonium 11 during the sulfoxide-catalyzed conversion of hemiacetal 3 to glycosyl sulfonate 10. ..
  51. Schröder S, Surmann J. Phototoxicity testing by online irradiation and HPLC. Anal Bioanal Chem. 2006;386:1695-700 pubmed
    ..In the pH 3 irradiation studies of CPZ and GMP, no reaction was detected between the molecules. ..
  52. Feldman K, Vidulova D. Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives. Org Lett. 2004;6:1869-71 pubmed
    ..reaction: see text] ..
  53. Huang J, Huang C, Chen W, Liu S, Hsu S, Chang H, et al. Independent [Ca2+]i increases and cell proliferation induced by the carcinogen safrole in human oral cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2005;372:88-94 pubmed
    The effect of the carcinogen safrole on intracellular Ca2+ movement and cell proliferation has not been explored previously. The present study examined whether safrole could alter Ca2+ handling and growth in human oral cancer OC2 cells...