Dimethyl Disulfide Derivatives

The following references dealing with mass spectrometry of dimethyldisulfide derivatives of unsaturated fatty acids have been collected as part of our regular literature searches for research purposes. The list is as comprehensive as we can manage but may not be exhaustive. References are listed alphabetically according to the surname of the first author, but not necessarily chronologically for a given author.

  • Albuquerque, L., Santos,J., Travassos,P., Nobre,M.F., Rainey,F.A., Wait,R., Empadinhas,N., Silva,M.T. and da Costa,M.S. Albidovulum inexpectatum gen. nov., sp. nov., a nonphotosynthetic and slightly thermophilic bacterium from a marine hot spring that is very closely related to members of the photosynthetic genus Rhodovulum. Appl. Environm. Microbiol., 68, 4266-4273 (2002).
  • Altabe, S.G., Aguilar,P., Caballero,G.M. and de Mendoza,D. The Bacillus subtilis acyl lipid desaturase is a 5 desaturase. J. Bact., 185, 3228-3231 (2003).
  • Attygalle, A.B., Jham,G.N., Svatos,A., Frighetto,R.T.S., Meinwald,J., Vilela,E.F., Ferrara,F.A. and Uchoa-Fernandes,M.A. Microscale, random reduction: application to the characterization of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, a new lepidopteran sex pheromone. Tetrahedron Letts., 36, 5471-5474 (1995).
  • Bell, M.V. Dick,J.R. and Pond,D.W. Octadecapentaenoic acid in a raphidophyte alga, Heterosigma akashiwo. Phytochemistry, 45, 303-306 (1997).
  • Biedermann, W., Lucker,E., Porschmann,J., Lachhab,S., Truyen,U. and Hensel,A. Structural characterisation of some fatty acids from the brain as biomarkers of BSE risk material. Anal. Bioanal. Chem., 379, 1031-1038 (2004).
  • Blokker, P., Schouten,S., Van den Ende,H., De Leeuw,J.W. and Damste,J.S.S. Cell wall-specific omega-hydroxy fatty acids in some freshwater green microalgae. Phytochemistry, 49, 691-695 (1998).
  • Buser, H-R., Arn,H., Geurin,P. and Rauscher,S. Determination of double bond position in monounsaturated acetates by mass spectrometry of dimethyldisulfide adducts. Anal. Chem., 55, 818-822 (1983).
  • Carballeira, N.M. and Alicea,J. The first naturally occurring alpha-methoxylated branched-chain fatty acids from the phospholipids of Amphimedon complanata. Lipids, 36, 83-87 (2001).
  • Carballeira, N.M. and Alicea,J. Novel methoxylated FA from the Caribbean sponge Spheciospongia cuspidifera. Lipids, 37, 305-308 (2002).
  • Carballeira, N.M. and Cruz,C. Dimethyldisulfide derivatization of ethyl (9Z,12Z)-9,12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate. Chem. Phys. Lipids, 84, 81-85 (1996).
  • Carballeira, N.M. and Emiliano,A. Novel brominated phospholipid fatty acids from the Caribbean sponge Agelas sp. Lipids, 28, 763-766 (1993).
  • Carballeira, N.M. and Medina,J.R. New delta(5,9)-fatty acids in the phospholipids of the sea anemone Stoichactis helianthus. J. Nat. Prod., 57, 1688-1695 (1994).
  • Carballeira, N.M. and Rodriguez,J. Two novel phospholipid fatty acids from the Caribbean sponge Geodia gibberosa. Lipids, 26, 324-326 (1991).
  • Carballeira, N.M. and Sepulveda,J.A. Two novel naturally occurring α-methoxy acids from the phospholipids of two Caribbean sponges. Lipids, 27, 72-74 (1992).
  • Carballeira, N.M. and Shalabi,F. Novel brominated phospholipid fatty acids from the Caribbean sponge Petrosia sp. J. Nat. Prod., 56, 739-746 (1993).
  • Carballeira, N.M. and Shalabi,F. The rare Caribbean sponge Leucosolenia canariensis: phospholipid fatty acids and sterols. Lipids, 30, 467-470 (1995).
  • Carballeira, N.M. and Shalabi,F. Unusual lipids in the Caribbean sponges Amphimedon viridis and Desmapsamma anchorata. J. Nat. Prod., 57, 1152-1159 (1994).
  • Carballeira, N.M., Cruz,H. and Ayala,N.L. Total synthesis of 2-methoxy-14-methylpentadecanoic acid and the novel 2-methoxy-1 4-methylhexadecanoic acid identified in the sponge Agelas dispar. Lipids, 37, 1033-1037 (2002).
  • Carballeira, N.M., Cruz,H., Hill,C.A., De Voss,J.J. and Garson,M. Identification and total synthesis of novel fatty acids from the siphonarid limpet Siphonaria denticulate. J. Nat. Prod., 64, 1426-1429 (2001).
  • Carballeira, N.M., Guzman,A., Nechev,J.T., Lahtchev,K., Ivanova,A. and Stefanov,K. Unusual lipid composition of a Bacillus sp isolated from Lake Pomorie in Bulgaria. Lipids, 35, 1371-1375 (2000).
  • Carballeira, N.M., Negron,V. and Reyes,E.D. Novel naturally occurring alpha-methoxy acids from the phospholipids of Caribbean sponges. Tetrahedron, 48, 1053-1058 (1992).
  • Carballeira, N.M., Oyola,D., Vicente,J. and Rodriguez,A.D. Identification of novel alpha-methoxylated phospholipid fatty acids in the caribbean sponge Erylus goffrilleri. Lipids, 42, 1047-1053 (2007).
  • Carballeira, N.M., Pagan,M., Shalabi,F., Nechev,J.T., Lahtchev,K., Ivanova,A. and Stefanov K. Two novel iso-branched octadecenoic acids from a Micrococcus species. J. Nat. Prod., 63, 1573-1575 (2000).
  • Carballeira, N.M., Reyes,M., Sostre,A., Huang,H.S., Verhagen,M.F.J.M. and Adams,M.W.W. Unusual fatty acid compositions of the hyperthermophilic archaeon Pyrococcus furiosus and the bacterium Thermotoga maritima. J. Bact., 179, 2766-2768 (1997).
  • Carballeira, N.M., Shalabi,F. and Cruz,C. Thietane, tetrahydrothiophene and tetrahydrothiopyran formation in reaction of methylene-interrupted dienoates with dimethyl disulfide. Tetrahedron Letts., 35, 5575-5578 (1994).
  • Carballeira, N.M., Shalabi,F. and Reyes,M. New 2-hydroxy fatty acids in the Caribbean urchin Tripneustes esculentus. J. Nat. Prod., 57, 614-619 (1994).
  • Carballeira, N.M., Shalabi,F., Stefanov,K., Dimitrov,K., Popov,S., Kujumgiev,A. and Andreev,S. Comparison of the fatty acids of the tunicate Botryllus schlosseri from the Black Sea with two associated bacterial strains. Lipids, 30, 677-679 (1995).
  • Carballeira, N.M., Sostre,A., Stefanov,K., Popov,S., Kujumgiev,A., Dimitrova-Konaklieva,S., Tosteson,C.G. and Tosteson,T.R. The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix, identification of the novel 9-methyl-10-hexadecenoic acid. Lipids, 32, 1271-1275 (1997).
  • Christie, W.W. Gas chromatography mass spectrometry methods for structural analysis of fatty acids. Lipids, 33, 343-353 (1998).
  • Christie, W.W. Structural analysis of fatty acids. In: Advances in Lipid Methodology - Four, pp. 119-169 (edited by W.W. Christie, Oily Press, Dundee) (1997).
  • Christie, W.W. and Han, X. Lipid Analysis - Isolation, Separation, Identification and Lipidomic Analysis (4th edition), 446 pages (Oily Press, Bridgwater, U.K. and Woodhead Publishing Ltd, Cambridge, U.K.) (2010) - Woodhead Publishing Ltd.
  • Christie, W.W., Brechany,E.Y. and Shukla,V.K.S. Analysis of seed oils containing cyclopentenyl fatty acids by combined chromatographic procedures. Lipids, 24, 116-120 (1989).
  • Cvacka, J., Kofronova,E., Vasickova,S., Stransky,K., Jiros,P., Hovorka,O., Kindl,J. and Valterova,I. Unusual fatty acids in the fat body of the early nesting bumblebee, Bombus pratorum. Lipids, 43, 441-450 (2008).
  • Dowd, M.K. Identification of the unsaturated heptadecyl fatty acids in the seed oils of Thespesia populnea and Gossypium hirsutum. J. Am. Oil Chem. Soc., 89, 1599-1609 (2012).
  • Dunkelblum, E., Tan,S.H. and Silk,P.J. Double bond location in monounsaturated fatty acids by dimethyl disulfide derivatisation and mass spectrometry. J. Chem. Ecol., 11, 265-277 (1985).
  • Elvert, M., Boetius,A., Knittel,K. and Jorgensen,B.B. Characterization of specific membrane fatty acids as chemotaxonomic markers for sulfate-reducing bacteria involved in anaerobic oxidation of methane. Geomicrobiol. J., 20, 403-419 (2003).
  • Evershed, R.P., Dudd,S.N., Copley,M.S., Berstan,R., Stott,A.W., Mottram,H., Buckley,S.A. and Crossman,Z. Chemistry of archaeological animal fats. Acc. Chem. Res., 35, 660-668 (2002).
  • Francis, G.W. and Veland,K. Alkylthiolation for the determination of double-bond positions in linear alkenes. J. Chromatogr., 219, 379-384 (1981).
  • Fukuda, Y. and Ando,Y. Occurrence of all-cis-5,8,11,14,17,20,23-hexacosaheptaenoic acid (26:7n-3) in roughscale sole Clidoderma asperrimum flesh lipids. Fisheries Sci., 77, 875-882 (2011).
  • Gao, J.M., Wang,C.Y., Zhang,A.L. and Liu,J.K. A new trihydroxy fatty acid from the ascomycete, Chinese truffle Tuber indicum. Lipids, 36, 1365-1370 (2001).
  • Golebiowski, M., Bogus,M.I., Paszkiewicz,M. and Stepnowski,P. Cuticular lipids of insects as potential biofungicides: methods of lipid composition analysis. Anal. Bioanal. Chem., 399, 3177-3191 (2011).
  • Imai, H., Yamamoto,K., Shibahara,A., Miyatani,S. and Nakayama,T. Determining double-bond positions in monoenoic 2-hydroxy fatty acids of glucosylceramides by gas chromatography-mass spectrometry. Lipids, 35, 233-236 (2000).
  • Imbs, A.B. and Rodkina,S.A. Isolation of 2-methyl branched unsaturated very long fatty acids from marine sponge Halichondria panicea and identification of them by GC-MS and NMR. Chem. Phys. Lipids, 129, 173-181 (2004).
  • Imbs, A.B. and Rodkina,S.A. Trans and positional ethylenic bonds in two dominant isomers of eicosapentaenoic acid from the freshwater sponge Baicalospongia bacillifera. Lipids, 40, 963-968 (2005).
  • Kakela, R., Hyvarinen,H. and Vainiotalo,P. Unusual fatty acids in the depot fat of the Canadian beaver (Castor canadensis). Comp. Biochem. Physiol. B, 113, 625-629 (1996).
  • Kalacheva, G.S. and Volova,T.G. Fatty acid composition of Wautersia eutropha lipids under conditions of active polyhydroxyalkanoates synthesis. Microbiology, 76, 535-540 (2007).
  • Kool, D.M., Zhu, B.L., Rijpstra, W.I.C., Jetten, M.S.M., Ettwig, K.F. and Damste, J.S.S. Rare branched fatty acids characterize the lipid composition of the intra-aerobic methane oxidizer "Candidatus methylomirabilis oxyfera". Appl. Environm. Microbiol., 78, 8650-8656 (2012).
  • Laverroux,S., Glasser,F., Gillet,M., Joly,C. and Doreau,M. Isomerization of vaccenic acid to cis and trans C18:1 isomers during biohydrogenation by rumen microbes. Lipids, 46, 843-850 (2011).
  • Kuwahara,Y., Samejima,M., Sakata,T., Kurosa,K., Sato,M., Matsuyama,S. and Suzuki,T. Chemical ecology of astigmatid mites. 44. identification of (Z,Z,Z)-5,9,12-octadecatrienoic acid and (Z,Z)-5,9-octadecadienoic acid as possible biosynthetic precursors of new hydrocarbons (Z,Z,Z)-4,8,11-heptadecatriene and (Z,Z)-4,8-heptadecadiene found in the astigmatid mite, Tortonia sp. Appl. Entomol. Zool., 30, 433-441 (1995).
  • Leonhardt,B.A. and DeVilbiss,E.D. Separation and double bond determination on nanogram quantities of aliphatic monounsaturated alcohols, aldehydes and fatty acid methyl esters. J. Chromatogr. A, 322, 484-490 (1985).
  • Mansour,M.P., Holdsworth,D.G., Forbes,S.E., Macleod,C.K. and Volkman,J.K. High contents of 24:6(n-3) and 20:1(n-13) fatty acids in the brittle star Amphiura elandiformis from Tasmanian coastal sediments. Biochem. System. Ecol., 33, 659-674 (2005).
  • Matsuoka,K., Yamamoto,M., Yamakawa,R., Muramatsu,M., Naka,H., Kondo,Y. and Ando,T. Identification of novel C-20 and C-22 trienoic acids from arctiid and geometrid female moths that produce polyenyl type II sex pheromone components. J. Chem. Ecol., 34, 1437-1445 (2008).
  • Mazzella,N., Molinet,J., Syakti,A.D., Barriol,A., Dodi,A., Bertrand,J.C. and Doumenq,P. Effects of pure n-alkanes and crude oil on bacterial phospholipid classes and molecular species determined by electrospray ionization mass spectrometry. J. Chromatogr. B, 822, 40-53 (2005).
  • Meija,J. and Soukup,V.G. Phenyl-terminated fatty acids in seeds of various aroids. Phytochemistry, 65, 2229-2237 (2004).
  • Mejanelle,L., Laureillard,J. and Saliot,A. Novel marine flagellate fatty acid: structural elucidation by GC-MS analysis of DMOX derivatives and DMDS adducts. J. Microb. Methods, 48, 221-237 (2002).
  • Mosley,E.E. and McGuire,M.A. Methodology for the in vivo measurement of the Delta(9)-desaturation of myristic, palmitic, and stearic acids in lactating dairy cattle. Lipids 42, 939-945 (2007).
  • Mosley,E.E., Shafii,B., Moate,P.J. and McGuire,M.A. cis-9, trans-11 Conjugated linoleic acid is synthesized directly from vaccenic acid in lactating dairy cattle. J. Nutr., 136, 570-575 (2006).
  • Mosley,E.E., Powell,G.L., Riley,M.B. and Jenkins,T.C. Microbial biohydrogenation of oleic acid to trans isomers in vitro. J. Lipid Res., 43, 290-296 (2002).
  • Mosley,E.E., Shafii,B., Moate,P.J. and McGuire,M.A. cis-9, trans-11 Conjugated linoleic acid is synthesized directly from vaccenic acid in lactating dairy cattle. J. Nutr., 136, 570-575 (2006).
  • Mosley,E.E., Wright,E.L., McGuire,M.K. and McGuire,M.A. trans Fatty acids in milk produced by women in the United States. Am. J. Clin. Nutr., 82, 1292-1297 (2005).
  • Moss,C.W. and Daneshvar,M.I. Identification of some uncommon monounsaturated fatty acids of bacteria. J. Clin. Microbiol., 30, 2511-2512 (1992).
  • Mottram,H.R., Dudd,S.N., Lawrence,G.J., Stott,A.W. and Evershed,R.P. New chromatographic, mass spectrometric and stable isotope approaches to the classification of degraded animal fats preserved in archaeological pottery. J. Chromatogr. A, 833, 209-221 (1999).
  • Nichols,P.D. and Nichols,C.A.M. Microbial signature lipid profiling and exopolysaccharides: Experiences initiated with Professor David C White and transported to Tasmania, Australia. J. Microbiol. Methods, 74, 33-46 (2008).
  • Nichols,P.D., Guckert,J.B. and White,D.C. Determination of monounsaturated double bond position and geometry for microbial monocultures and complex consortia by capillary gas chromatography-mass spectrometry of their dimethyl disulfide adducts. J. Microbiol. Methods, 5, 49-55 (1986).
  • Nichols,P.D., Volkman,J.K. and Everitt,D.A. Occurrence of 6-hexadecenoic acid and other unusual monounsaturated fatty acids in the lipids of oceanic particulate matter. Oceanol. Acta, 12, 393-403 (1989).
  • Palusinska-Szysz,M., Turska-Szewczuk,A., Karas,M., Russa,R. and Drozanski,W.J. Occurrence of new polyenoic very long chain acyl residues in lipids from Acanthamoeba castellanii. Acta Protozool., 48, 63-72 (2009).
  • Pepe, C. and Dif,K. The use of ethanethiol to locate the triple bond in alkynes and the double bond in substituted alkenes by gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom., 15, 97-103 (2001).
  • Pepe, C., Balcar,N., Dizabo,P., Dagaut,J., Saliot,A., Couffignal,R. and Sayer,H. Determination of positions of double bonds in diunsaturated esters and a disubstituted gamma-lactone by means of GC/MS of dimethyl disulfide derivatives. Rapid Commun. Mass Spectrom., 9, 1576-1579 (1995).
  • Pepe, C., Sayer,H., Balcar,N., Dagaut,J. and Couffignal,R. Determination of the position of the double bonds in di-unsaturated compounds by means of gas chromatography mass spectrometry of dimethyl disulfide derivatives. Eur. Mass Spectrom., 3, 465-469 (1997).
  • Proell, J.M., Mosley,E.E., Powell,G.L. and Jenkins,T.C. Isomerization of stable isotopically labeled elaidic acid to cis and trans monoenes by ruminal microbes. J. Lipid Res., 43, 2072-2076 (2002).
  • Rochut, S., Dif,K., Paumard,J.P. and Pepe,C. The location of the double bonds in substituted conjugated alkadienes by using the ethanethiol and gas chromatography/mass spectrometry. Comptes Rendus Chimie, 5, 157-162 (2002).
  • Rontani, J.F. Electron ionization mass spectrometric determination of double bond position in monounsaturated alpha,beta- and beta,gamma-isomeric isoprenoid acids. Rapid Commun. Mass Spectrom., 12, 961-967 (1998).
  • Rontani, J.F., Koblizek,M., Beker,B., Bonin,P.and Kolber,Z.S. On the origin of cis-vaccenic acid photodegradation products in the marine environment. Lipids, 38, 1085-1092 (2003).
  • Saito, T. and Ochiai,H. Identification of a novel all-cis-5,9,12-heptadecatrienoic acid in the cellular slime mold Polysphondylium pallidum. Lipids, 31, 445-447 (1996).
  • Saito, T. and Ochiai,H. Fatty acid composition of the cellular slime mold Polysphondylium pallidum. Lipids, 33, 327-332 (1998).
  • Sansone, A., Melchiorre, M., Chatgilialoglu, C. and Ferreri, C. Hexadecenoic fatty acid isomers: a chemical biology approach for human plasma biomarker development. Chem. Res. Toxicol., 26, 1703-1709 (2013).
  • Sato, D., Ando,Y., Tsujimoto,R. and Kawasaki,K. Identification of novel nonmethylene-interrupted fatty acids, 7E,13E-20: 2, 7E,13E,17Z-20:3, 9E,15E,19Z-22:3, and 4Z,9E,15E,19Z-22:4, in Ophiuroidea (brittle star) lipids. Lipids, 36, 1371-1375 (2001).
  • Scribe, P., Guezennec,J., Dagaut,J., Pepe,C. and Saliot,A. Identification of the position and stereochemistry of the double bond in monounsaturated fatty acid methyl esters by gas chromatography/mass spectrometry of dimethylsulfide derivatives. Anal. Chem., 80, 928-931 (1988).
  • Shibahara, A., Yamamoto,K., Kinoshita,A. and Anderson,B.L. An improved method for preparing dimethyl disulfide adducts for GC/MS analysis. J. Am. Oil Chem. Soc., 85, 93-94 (2008).
  • Shibahara, A., Yamamoto,K., Nakayama,T. and Kajimoto,G. Rapid determination of double bond positions in monounsaturated FA by gas chromatography-mass spectrometry and its application to fatty acid analysis. Yukagaku, 34, 618-625 (1985).
  • Shibahara, A., Yamamoto,K., Nakayama,T. and Kajimoto,G. cis-Vaccenic acid in mango pulp lipids. Lipids, 21, 388-394 (1986).
  • Shibahara, A., Yamamoto,K., Nakayama,T. and Kajimoto,G. cis-Vaccenic acid in pulp lipids of commonly available fruits. J. Am. Oil Chem. Soc., 64, 397-401 (1987).
  • Shibahara, A., Yamamoto,K., Takeoka,M., Kinoshita,A., Kajimoto,G., Nakayama,T. and Noda,M. Application of a GC-MS method using deuterated fatty acids for tracing cis-vaccenic acid biosynthesis in kaki pulp. Lipids, 24, 488-493 (1989).
  • Shibahara, A., Yamamoto,K., Shinkai,K., Nakayama,T. and Kajimoto,G. cis-9,cis-15-Octadecadienoic acid: a novel fatty acid found in higher plants. Biochim. Biophys. Acta, 1170, 245-252 (1993).
  • Son, B.W., Kim,J.C. and Choi,H.D. A new diacylgalactolipid containing 4Z-16:1 from the marine cyanobacterium Oscillatoria sp. Lipids, 36, 427-429 (2001).
  • Tanaka, T., Shibata,K., Hino,H., Murashita,T., Kayama,M. and Satouchi,K. Purification and gas chromatographic mass spectrometric characterization of non-methylene interrupted fatty acid incorporated in rat liver. J. Chromatogr. B, 700, 1-8 (1997).
  • Thies, W. Determination of the petroselinic acid content in seeds of Coriandrum sativum by GLC. Fat Sci. Technol., 95, 20-23 (1993).
  • Tsevegsuren, N., Aitzetmuller,K. and Vosman,K. Isomers of hexadecenoic and hexadecadienoic acids in Androsace septentrionalis (Primulaceae) seed oil. Lipids, 38, 1173-1178 (2003).
  • Vincenti, M., Guglieilmetti,G., Cassani,G. and Tonini,C. Determination of double bond position in diunsaturated compounds by mass spectrometry of dimethyl disulfide derivatives. Anal. Chem., 59, 694-699 (1987).
  • Virtue, P., Nichols,P.D. and Boon,P.I. Simultaneous estimation of microbial phospholipid fatty acids and diether lipids by capillary gas chromatography. J. Microb. Methods, 25, 177-185 (1996).
  • Volkman, J.K., Burger-Wiersma,T., Nichols,P.D. and Summons,R.E. Lipids and chemotaxonomy of Prochlorothrix hollandica, a planktonic prokaryote containing chlorophylls a and b. J. Phycol., 24, 554-559 (1988).
  • Vyssotski, M., Lee,K.C.Y., Lagutin,K., Ryan,J., Morgan,X.C. and Stott,M.B. Fatty acids of Chthonomonas calidirosea, of a novel class Chthonomonadetes from a recently described phylum Armatimonadetes. Lipids, 46, 1155-1161 (2011)
  • Whittle, E., Cahoon,E.B., Subrahmanyam,S. and Shanklin,J. A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English Ivy) can synthesize 16- and 18-carbon monoene and diene products. J. Biol. Chem., 280, 28169-28176 (2005).
  • Yamamoto, K., Shibahara,A., Nakayama,T. and Kajimoto,G. Double bond localization in heneicosapentaenoic acid by a GC/MS method. Lipids, 26, 948-950 (1991).
  • Yamamoto, K., Shibahara,A., Nakayama,T. and Kajimoto,G. Determination of double bond positions in methylene-interrupted dienoic fatty acids by GC-MS as their dimethyl disulfide adducts. Chem. Phys. Lipids, 60, 39-50 (1991).
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  • Zelles, L. and Bai, Q.Y. Fractionation of fatty acids derived from soil lipids by solid phase extraction and their quantitative analysis by GC-MS. Soil Biol. Biochem., 25, 495-507 (1993).

Updated February 5, 2014