Skip to main content
SpringerLink
Log in

Origin, occurrence, and biodegradation of long-side-chain alkyl compounds in the environment: a review

  • Published:
Environmental Geochemistry and Health Aims and scope Submit manuscript

Abstract

Long-side-chain alkyl compounds, such as those present in oil and oil products, either of natural or of anthropogenic origin or released by industrial activities, are a ubiquitous group of chemicals in the environment. Among them, long-side-chain alkylmonocycloalkanes, alkylbenzenes, and alkyl organic sulfur compounds are largely found in fossil fuels while long-side-chain alkylbenzene sulfonates and alkylphenols are released into the environment primarily due to domestic activities. The present article briefly summarizes the advances that have occurred in this field in terms of the identity, abundance, possible origin and significance of these long-side-chain alkyl compounds found in the environment. In addition, the susceptibility to biodegradation and the fate of these chemicals in the environment are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • M Ahel C Schaffner W. Giger (1996) ArticleTitleBahaviour of alkylphenol polyethoxylates in the aquatic environment-III. Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater Water Res 30 37–46 Occurrence Handle10.1016/0043-1354(95)00123-3

    Article  Google Scholar 

  • J Albaiges J Algaba E Clavell J Grimalt (1986) ArticleTitlePetroleum geochemistry of the Taragona Basin (Spanish Mediterranean offshore) Org Geochem 10 441–450 Occurrence Handle10.1016/0146-6380(86)90044-6

    Article  Google Scholar 

  • M. Alexander (1973) ArticleTitleNonbiodegradable and other recalcitrant molecules Biotechnol Bioeng 15 611–647 Occurrence Handle10.1002/bit.260150402

    Article  Google Scholar 

  • OO Amund IJ. Higgins (1985) ArticleTitleThe degradation of 1-phenylalkanes by an oil-degrading strain of Acinetobacter lwoffi Antonie van Leeuwenhoek 51 45–56 Occurrence Handle10.1007/BF00444227 Occurrence Handle4004202

    Article  PubMed  Google Scholar 

  • A Arukwe A Goksoyr R Thibaut JP Cravedi (2000) ArticleTitleMetabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar) Mar Environ Res 50 141–145 Occurrence Handle10.1016/S0141-1136(00)00081-7 Occurrence Handle11460680

    Article  PubMed  Google Scholar 

  • G Baggi P Barbieri E Galli S. Tollari (1987) ArticleTitleIsolation of a Pseudomonas stutzeri strain that degrades o-xylene Appl Environ Microbiol 53 2129–2132 Occurrence Handle3674872

    PubMed  Google Scholar 

  • A Barbe JO Grimalt J. Albaiges (1988) ArticleTitleNovel cyclohexyl isoprenoid hydrocarbons in carbonate-evaporite crude oils Naturwissenschaften 75 624–625 Occurrence Handle10.1007/BF00366478

    Article  Google Scholar 

  • ZH Baset RJ Panarov TR Ashe (1980) Organic compound in coal: structure and origin AJ Douglas JR Maxwell (Eds) Advances in Organic Geochemistry Pergamon Press Oxford United Kingdom 619–630

    Google Scholar 

  • JM Bayona J. Albaiges (1986) ArticleTitleSelective aerobic degradation of linear alkylbenzenes by pure microbial cultures Chemosphere 15 595–598 Occurrence Handle10.1016/0045-6535(86)90007-X

    Article  Google Scholar 

  • HW Beam JJ. Perry (1974) ArticleTitleMicrobial degradation and assimilation of n-alkyl-substituted cycloparaffins J Bacteriol 118 394–399 Occurrence Handle4597441

    PubMed  Google Scholar 

  • ER Bennett CD Metcalfe (1998) ArticleTitleDistribution of alkylphenol compounds in Great Lake sediments: United States and Canada Environ Toxicol Chem 16 1230–1235 Occurrence Handle10.1897/1551-5028(1998)017<1230:DOACIG>2.3.CO;2

    Article  Google Scholar 

  • DT Bennie CA Sullivan H-B Lee TE Peart RJ Maguire (1996) ArticleTitleOccurrence of alkylphenols and alkylphenol mono- and diethoxylates in natural waters Sci Total Environ 193 263–275

    Google Scholar 

  • J Campos-Garcia A Esteve R vazquez-Duhalt JL Ramos G. Soberon-Chavez (1999) ArticleTitleThe branched-chain dodecylbenzene sulfonate degradation pathway of Pseudomonas aeruginosa W51D involves a novel route for degradation of the surfactant lateral alkyl chain Appl Environ Microbiol 65 3730–3734 Occurrence Handle10427075

    PubMed  Google Scholar 

  • K Christoffersen BW Hansen L Johansson E. Skrog (2003) ArticleTitleInfluence of LAS on marine calanoid copepod population dynamics and potential reproduction Aqua Toxicol 63 405–416 Occurrence Handle10.1016/S0166-445X(02)00200-X

    Article  Google Scholar 

  • J. Connan (1984) Biodegradation of crude oils in reservoirs J Brooks D Welte (Eds) Advances in Petroleum Geochemistry Academic Press London 299–335

    Google Scholar 

  • C.-D. Czogalla F. Boberg (1983) ArticleTitleSulfur compounds in fossil fuels I Sulfur Rep 3 121–167

    Google Scholar 

  • JB Davis RL. Raymond (1961) ArticleTitleOxidation of alkyl-substituted cyclic hydrocarbons by a Nocardia during growth on n-alkanes Appl Microbiol 9 383–388 Occurrence Handle13720182

    PubMed  Google Scholar 

  • JJ Defrank DW. Ribbons (1977) ArticleTitlep-Cymene pathway in Pseudomonas putida: initial reactions J Bacteriol 129 1356–1364 Occurrence Handle845117

    PubMed  Google Scholar 

  • S Derenne C Largeau E Casadevall JS Sinninghe Damste EW Tegelaar JW Leeuw Particlede (1990) ArticleTitleCharacterization of Estonian Kukersite by spectroscopy and pyrolysis: evidence for abundant alkyl phenolic moieties in an Ordovician, marine, type II/I kerogen Org Geochem 16 873–888 Occurrence Handle10.1016/0146-6380(90)90124-I

    Article  Google Scholar 

  • M Rosa ParticleDe A Gambacorta L Minale JD Bu’lock (1972) ArticleTitleThe formation of ω-cyclo-hexyl fatty acids from shikimate in an␣acidophilic thermophilic bacillus Biochem J 128 751–754 Occurrence Handle4638790

    PubMed  Google Scholar 

  • JZ Dong K. Ouchi (1989) ArticleTitleGeochemical origin of long chain alkylaromatics in coal. 1. Model reaction of fatty acid or alcohol with phenol Fuel 68 710–716 Occurrence Handle10.1016/0016-2361(89)90208-1

    Article  Google Scholar 

  • JZ Dong WP Vorkink ML Lee (1993) ArticleTitleOrigin of long-chain alkylcyclohexanes and alkylbenzenes in a coal-bed wax Geochim Cosmochim Acta 57 837–849 Occurrence Handle10.1016/0016-7037(93)90172-S

    Article  Google Scholar 

  • AG Douglas JS Sinninghe Damste MG Fowler TI Eglinton JW. Leeuw Particlede (1991) ArticleTitleUnique distribution of hydrocarbons and sulfur compounds released by flash pyrolysis from the fossilised alga Gloeocapsomorpha prisca, a major constituent in one of four Ordovician kerogens Geochim Cosmochim Acta 55 275–291 Occurrence Handle10.1016/0016-7037(91)90417-4

    Article  Google Scholar 

  • TK Dutta IC Gunsalus (1997) ArticleTitleReductase gene and protein structure: p-cymene methyl hydroxylase Biochem Biophys Res Commun 233 502–506 Occurrence Handle10.1006/bbrc.1997.6493 Occurrence Handle9144566

    Article  PubMed  Google Scholar 

  • TK Dutta S. Harayama (2000) ArticleTitleFate of crude oil by the combination of photooxidation and biodegradation Environ Sci Technol 34 1500–1505 Occurrence Handle10.1021/es991063o

    Article  Google Scholar 

  • TK Dutta S. Harayama (2001a) ArticleTitleBiodegradation of n-alkylcycloalkanes and n-alkylbenzenes via new pathways in Alcanivorax sp. Strain MBIC 4326 Appl Environ Microbiol 67 1970–1974 Occurrence Handle10.1128/AEM.67.4.1970-1974.2001

    Article  Google Scholar 

  • TK Dutta S. Harayama (2001b) ArticleTitleTime-of-flight mass spectrometric analysis of high-molecular-weight alkanes in crude oil by silver nitrate chemical ionization after laser desorption Anal Chem 73 864–869 Occurrence Handle10.1021/ac0009797

    Article  Google Scholar 

  • TK Dutta S. Harayama (2001) ArticleTitleAnalysis of long-side-chain alkylaromatics in crude oil for evaluation of their fate in the environment Environ Sci Technol 35 102–107 Occurrence Handle10.1021/es001165a Occurrence Handle11351990

    Article  PubMed  Google Scholar 

  • TK Dutta SA Selifonov IC Gunsalus (1998) ArticleTitleOxidation of methyl-substituted naphthalenes: pathways in a versatile Sphingomonas paucimobilis strain Appl Environ Microbiol 64 1884–1889 Occurrence Handle9572967

    PubMed  Google Scholar 

  • RP. Eganhouse (1986) ArticleTitleLong-chain alkylbenzenes: their analytical chemistry, environmental occurrence and fate Intern J Environ Anal Chem 26 241–263

    Google Scholar 

  • RP Eganhouse DL Blumfield IR. Kaplan (1983) ArticleTitleLong-chain alkylbenzenes as molecular tracers of domestic wastes in the marine environment Environ Sci Technol 17 523–530 Occurrence Handle10.1021/es00115a006

    Article  Google Scholar 

  • L Ellis RI Kagi R. Alexander (1992) ArticleTitleSeparation of petroleum hydrocarbons using dealuminated mordenite molecular sieve. I. Monoaromatic hydrocarbons Org Geochem 18 587–593 Occurrence Handle10.1016/0146-6380(92)90084-B

    Article  Google Scholar 

  • L Ellis RK Singh R Alexander RI Kagi (1995) ArticleTitleGeosynthesis of organic compounds. III. Formation of alkyltoluenes and alkylxylenes in sediments Geochim Cosmochim Acta 59 5133–5140 Occurrence Handle10.1016/0016-7037(95)00352-5

    Article  Google Scholar 

  • L Ellis TA Langworthy R. Winans (1996) ArticleTitleOccurrence of phenylalkanes in some Australian crude oils and sediments Org Geochem 24 57–69 Occurrence Handle10.1016/0146-6380(96)00006-X

    Article  Google Scholar 

  • BD Ensley (1984) Microbial metabolism of condensed thiophenes DT Gibson (Eds) Microbial Degradation of Organic Compounds Marcel Dekker Inc. New York 309–317

    Google Scholar 

  • PM Fedorak DWS Westlake (1986) ArticleTitleFungal metabolism of n-alkylbenzenes Appl Environ Microbiol 51 435–437

    Google Scholar 

  • PM Fedorak JD Payzant DS Montgomery DWS. Westlake (1988) ArticleTitleMicrobial degradation of n-alkyl tetrahydrothiophenes found in petroleum Appl Environ Microbiol 54 1243–1248 Occurrence Handle3389816

    PubMed  Google Scholar 

  • EL Feinberg PIN Ramage PW. Trudgill (1980) ArticleTitleThe degradation of n-alkylcycloalkanes by a mixed bacterial culture J Gen Microbiol 121 507–511

    Google Scholar 

  • PL Ferguson CR Iden BJ. Brownawell (2001) ArticleTitleDistribution and fate of neutral alkylphenol ethoxylate metabolites in a sewage-impacted urban estuary Environ Sci Technol 35 2428–2435 Occurrence Handle10.1021/es001871b Occurrence Handle11432544

    Article  PubMed  Google Scholar 

  • F Ferrara F Fabietti M Delise AP Bocca E Funari (2001) ArticleTitleAlkylphenolic compounds in edible molluscs of the Adriatic Sea (Italy) Environ Sci Technol 35 3109–3112 Occurrence Handle11505985

    PubMed  Google Scholar 

  • MG Fowler AG Douglas (1984) ArticleTitleDistribution and structure of hydrocarbons in four organic-rich Ordovician rocks Org Geochem 6 105–114 Occurrence Handle10.1016/0146-6380(84)90031-7

    Article  Google Scholar 

  • MG Fowler P Abolins AG. Douglas (1986) ArticleTitleMonocyclic alkanes in Ordovician organic matters Org Geochem 10 815–823 Occurrence Handle10.1016/S0146-6380(86)80018-3

    Article  Google Scholar 

  • M Franska R Franski A Szymanski Z Lukaszewski (2003) ArticleTitleA central fission pathway in alkylphenol ethoxylate biodegradation Water Res 37 1005–1014 Occurrence Handle10.1016/S0043-1354(02)00444-X Occurrence Handle12553975

    Article  PubMed  Google Scholar 

  • RM Garrett IJ Pickering CE Haith RC Prince (1998) ArticleTitlePhotooxidation of crude oil Environ Sci Technol 32 3719–3723 Occurrence Handle10.1021/es980201r

    Article  Google Scholar 

  • JO Grimalt M Griffol AM Solanas J. Albaiges (1991) ArticleTitleMicrobial degradation of marine evaporitic crude oils Geochim Cosmochim Acta 55 1903–1913 Occurrence Handle10.1016/0016-7037(91)90032-Z

    Article  Google Scholar 

  • Hall PB, Douglas AG 1983. The distribution of cyclic alkanes in two lacustrine deposits. In Bjoroy et al. eds. Advances in Organic Geochemistry.: J. Wiley, pp. 576–587.

  • M Hampel J Blasco (2002) ArticleTitleToxicity of linear alkylbenzene sulfonate and one long-chain degradation intermediate, sulfophenyl carboxylic acid on early life-stages of seabream (sparus aurata) Ecotoxicol Environ Saf 51 53–59 Occurrence Handle10.1006/eesa.2001.2106 Occurrence Handle11800550

    Article  PubMed  Google Scholar 

  • Hansen RP. (1967). 11-Cyclohexyl undecanoic acid: its occurrence in bovine rumen bacteria. Chem Ind. 1640–1641

  • PC Hartmann JG Quinn JW King S Tsutsumi H. Takada (2000) ArticleTitleIntercalibration of LABs in marine sediment SRM1941a and their application as a molecular marker in Narragansett Bay sediments Environ Sci Technol 34 900–906 Occurrence Handle10.1021/es990798q

    Article  Google Scholar 

  • M Hawrelak E Bennett C. Metcalfe (1999) ArticleTitleThe environmental fate of the primary degradation products of alkylphenol ethoxylate surfactants in recycled paper sludge Chemosphere 39 745–752 Occurrence Handle10.1016/S0045-6535(99)00010-7 Occurrence Handle10448553

    Article  PubMed  Google Scholar 

  • DC Herman PM Fedorak JW. Costerton (1993) ArticleTitleBiodegradation of cycloalkane carboxylic acids in oil sand tailings Can J Microbiol 39 576–580 Occurrence Handle8358669

    PubMed  Google Scholar 

  • DC Herman PM Fedorak MD MacKinnon JW Costerton (1994) ArticleTitleBiodegradation of naphthenic acids by microbial populations indigenous to oil sands tailings Can J Microbiol 40 467–477 Occurrence Handle8050066

    PubMed  Google Scholar 

  • CF Hoffmann CB Foster TG Powell RE. Summons (1987) ArticleTitleHydrocarbon biomarkers from Ordovicians sediments and the fossil alga Gloeocapsomorpha prisca Zallessky 1917 Geochim Cosmochim Acta 51 2681–2697 Occurrence Handle10.1016/0016-7037(87)90149-9

    Article  Google Scholar 

  • FD Hostettler KA Kvenvolden (2002) ArticleTitleAlkylcyclohexanes in environmental geochemistry Environ Forensics 3 293–301

    Google Scholar 

  • LL Ingram J Ellis PT Crisp AC Cook (1983) ArticleTitleComparative study of oil shales and shale oils from the Mahogany Zone, Green River Formation (U.S.A.) and Kerosene Creek Seam, Rundle Formation (Australia) Chem Geol 38 185–212 Occurrence Handle10.1016/0009-2541(83)90054-2

    Article  Google Scholar 

  • J. Jensen (1999) ArticleTitleFate and effects of linear alkylbenzene sulphonates (LAS) in the terrestrial environment Sci Total Environ 226 93–111 Occurrence Handle10.1016/S0048-9697(98)00395-7 Occurrence Handle10085562

    Article  PubMed  Google Scholar 

  • ZS Jiang MG. Fowler (1986) Carotenoid-derived alkanes in oils from north-western China D Leythaeuser J Rullkotter (Eds) Advances in Organic Geochemistry Pergamon Journals Oxford 831–839

    Google Scholar 

  • WD Johns A Shimoyama (1971) ArticleTitleCatalytic conversion of fatty acids to petroleum-like paraffins and their maturation Nature 232 140–144

    Google Scholar 

  • E Kannenberg A Blume K. Poralla (1984) ArticleTitleProperties of ω-cyclohexane fatty acids in membranes FEBS Lett 172 331–334 Occurrence Handle10.1016/0014-5793(84)81151-5

    Article  Google Scholar 

  • IR Kaplan Y Galperin (1996) Application of alkylcyclohexane distribution pattern recognition for hydrocarbon fuel identification in environmental samples PT Kostecki EZ Calagrese M Bonazountas (Eds) Contaminated soils Lewis Publishers Chelsea MI 65–78

    Google Scholar 

  • IR Kaplan Y Galperin S-H Lu RP Lee (1997) ArticleTitleForensic environmental geochemistry: differentiation of fuel-types, their source and release time Org Geochem 27 289–317 Occurrence Handle10.1016/S0146-6380(97)87941-7

    Article  Google Scholar 

  • YV. Kissin (1990) ArticleTitleCatagenesis of light cycloalkanes in petroleum Org Geochem 15 575–594 Occurrence Handle10.1016/0146-6380(90)90103-7

    Article  Google Scholar 

  • KG Kropp PM. Fedorak (1998) ArticleTitleA review of the occurrence, toxicity, and biodegradation of condensed thiophenes found in petroleum Can J Microbiol 44 605–622 Occurrence Handle10.1139/cjm-44-7-605 Occurrence Handle9783422

    Article  PubMed  Google Scholar 

  • DA Kunz PJ. Chapman (1981) ArticleTitleCatabolism of pseudo cumene and 3-ethyltoluene by Pseudomonas putida (arvilla) mt2: evidence for new function of the TOL (pWW0) plasmid J Bacteriol 146 179–191 Occurrence Handle7216999

    PubMed  Google Scholar 

  • EJ Levy RR Doyle RA Brown FW. Melpolder (1961) ArticleTitleIdentification of components in paraffin wax by high temperature gas chromatography and mass spectrometry Anal Chem 33 698–704 Occurrence Handle10.1021/ac60174a016

    Article  Google Scholar 

  • RJ Maguire (1999) ArticleTitleReview of the persistence of nonylphenol and nonylphenol ethoxylates in aquatic environments Water Qual Res J Can 34 37–78

    Google Scholar 

  • MC Mahajan PS Phale CS. Vaidyanathan (1994) ArticleTitleEvidence for the involvement of multiple pathways in the biodegradation of 1- and 2-methylnaphthalene by Pseudomonas putida CSV86. Arch Microbiol 161 425–433 Occurrence Handle8042906

    PubMed  Google Scholar 

  • BJ Mair PE Eberly K Li FD. Rossini (1958) ArticleTitlePolycycloparaffin␣hydrocarbons in Petroleum. Ind Eng Chem 50 115–116 Occurrence Handle10.1021/ie50577a047

    Article  Google Scholar 

  • E Mangas MT Vaquero L Comellas F. Broto-Puig (1998) ArticleTitleAnalysis and fate of aliphatic hydrocarbons, linear alkylbenzenes, polychlorinated biphenyls and polycyclic aromatic hydrocarbons in sewage sludge-amended soils. Chemosphere 36 61–72 Occurrence Handle10.1016/S0045-6535(97)00350-0

    Article  Google Scholar 

  • March J. (1985) Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, 3rd edn. Wiley-Interscience

  • CG. Naylor (1992) ArticleTitleEnvironmental fate of alkylphenol ethoxylates Soap Chemical Specialities 68 27–32

    Google Scholar 

  • AC Nimrod WH. Benson (1996) ArticleTitleEnvironmental estrogenic effects of alkylphenol ethoxylates. Crit Rev Toxicol 26 355–364

    Google Scholar 

  • SB Ostroukhov OA Aref’yev VM Makushina MN Zabrodina AA. Petrov (1982) ArticleTitleMonocyclic hydrocarbons with isoprenoid chains. Neftekhimiya 22 723–728

    Google Scholar 

  • SB Ostroukhov OA Aref’yev SD Pustil’nikova MN Zabrodina AA. Petrov (1983) ArticleTitleC12–C30 n-alkylbenzenes in crude oils. Pet Chem USSR 23 1–12

    Google Scholar 

  • RP Philp TD. Gilbert (1986) ArticleTitleBiomarker distributions in Australian oils predominantly derived from terrigenous source material Org Geochem 10 73–84 Occurrence Handle10.1016/0146-6380(86)90010-0

    Article  Google Scholar 

  • M Radke H. Willsch (1993) ArticleTitleGeneration of alkylbenzenes and benzo[b]thiophenes by artificial thermal maturation of sulfur-rich coal Fuel 72 1103–1107 Occurrence Handle10.1016/0016-2361(93)90316-T

    Article  Google Scholar 

  • JF Rontani P. Bonin (1992) ArticleTitleUtilization of n-alkyl-substituted cyclohexanes by a marine Alcaligenes Chemosphere 24 1441–1446 Occurrence Handle10.1016/0045-6535(92)90266-T

    Article  Google Scholar 

  • JF Rontani P Bonin G. Giusti (1987) ArticleTitleMechanistic study of interactions between photo-oxidation and biodegradation of n-nonylbenzene in seawater Mar Chem 22 1–12 Occurrence Handle10.1016/0304-4203(87)90044-2

    Article  Google Scholar 

  • JF Rontani E Rambeloarisoa JC Bertrand G. Giusti (1985) ArticleTitleDegradation of alkyl-substituted benzenes and their photo-oxidation products by a marine mixed bacterial population Mar Environ Res 16 301–314 Occurrence Handle10.1016/0141-1136(85)90025-X

    Article  Google Scholar 

  • M Rosety FJ Ordonez M Rosety-Rodriguez JM Rosety I. Rosety (2003) ArticleTitleIn vitro acute toxicity of anionic surfactant linear alkylbenzene sulphonate (LAS) on the motility of gilthead (Sparus aurata L.) sperm Histol Histopathol 18 475–478 Occurrence Handle12647798

    PubMed  Google Scholar 

  • I Rubinstein OP. Strausz (1979) ArticleTitleGeochemistry of thiourea adduct fraction from an Alberta Petroleum Geochim Cosmochim Acta 43 1387–1392 Occurrence Handle10.1016/0016-7037(79)90129-7

    Article  Google Scholar 

  • FM Sariaslani DB Harper IJ. Higgins (1974) ArticleTitleMicrobial degradation of hydrocarbons. catabolism of 1-phenylalkanes by Nocardia salmonicolor Biochem J 140 31–45 Occurrence Handle4451551

    PubMed  Google Scholar 

  • Schaefle J, Ludwig B, Albrecht PA, Ourisson G. (1977) Hydrocarbures aromatiques d’origine geologique.II. Nouveaux cartenoides aromatique fossiles. Tetrahedron Lett 3673–3677

  • Y Shiraishi H Hara T Hirai I. Komasawa (1999a) ArticleTitleA deep desulfurization process for light oil by photosensitized oxidation using a triplet photosensitizer and hydrogen peroxide in an oil/water two-phase liquid-liquid extraction system Ind Eng Chem Res 38 1589–1595 Occurrence Handle10.1021/ie980651s

    Article  Google Scholar 

  • Y Shiraishi H Hara T Hirai I. Komasawa (1999b) ArticleTitleVisible light-induced deep desulfurization process for light oil by photochemical electron-transfer oxidation in an organic two-phase extraction system Ind Eng Chem Res 38 3310–3318 Occurrence Handle10.1021/ie990135h

    Article  Google Scholar 

  • JS Sinninghe Damste JW. Leeuw Particlede (1990) ArticleTitleAnalysis, structure and geochemical significance of organically-bound sulfur in the geosphere: state of the art and future research Org Geochem 16 1077–1101 Occurrence Handle10.1016/0146-6380(90)90145-P

    Article  Google Scholar 

  • JS Sinninghe Damste JW Leeuw Particlede AC Kock-van Dalen MA Zeeuw Particlede F Lange Particlede IC Rijpstra PA. Schenck (1987) ArticleTitleThe occurrence and identification of series of organic sulfur compounds in oils and sediment extracts. I. A study of Rozel Point Oil (U.S.A.) Geochim Cosmochim Acta 51 2369–2391 Occurrence Handle10.1016/0016-7037(87)90291-2

    Article  Google Scholar 

  • JS Sinninghe Damste AC Kock-van Dalen JW. Leeuw Particlede (1988) ArticleTitleIdentification of long-chain isoprenoid alkylbenzenes in sediments and crude oils Geochim Cosmochim Acta 52 2671–2677 Occurrence Handle10.1016/0016-7037(88)90035-X

    Article  Google Scholar 

  • JS Sinninghe Damste IC Rijpstra JW Leeuw Particlede PA. Schenck (1989a) ArticleTitleThe occurrence and identification of series of organic sulfur compounds in oils and sediment extracts. II. Their presence in samples from hypersaline and non-hypersaline palaeoenvironments and possible application as source, palaeoenvironmental and maturity indicators Geochim Cosmochim Acta 53 1323–1341 Occurrence Handle10.1016/0016-7037(89)90066-5

    Article  Google Scholar 

  • JS Sinninghe Damste IC Rijpstra AC Kock-van Dalen JW Leeuw Particlede PA. Schenck (1989b) ArticleTitleQuenching of labile functionalised lipids by inorganic sulfur species: Evidence for the formation of sedimentary organic sulfur compounds at the early stages of diagenesis Geochim Cosmochim Acta 53 1343–1355 Occurrence Handle10.1016/0016-7037(89)90067-7

    Article  Google Scholar 

  • JS Sinninghe Damste AC Kock-van Dalen PA Albrecht JW. Leeuw Particlede (1991) ArticleTitleIdentification of long-chain 1,2-di-n-alkylbenzenes in Amposta crude oil from the Tarragona Basin, Spanish Mediterranean: implication for the origin and fate of n-alkylbenzenes Geochim Cosmochim Acta 55 3677–3683 Occurrence Handle10.1016/0016-7037(91)90066-E

    Article  Google Scholar 

  • JS Sinninghe Damste BJ Keely SE Betts M Baas JR Maxwell JW. Leeuw Particlede (1993) ArticleTitleVariations in abundances and distributions of isoprenoid chromans and long-chain alkylbenzenes in sediments of the Mulhouse Basin: a molecular sedimentary record of palaeosalinity Org Geochem 20 1201–1215 Occurrence Handle10.1016/0146-6380(93)90009-Z

    Article  Google Scholar 

  • MR. Smith (1990) ArticleTitleThe biodegradation of aromatic hydrocarbons by bacteria Biodegradation. 1 191–206 Occurrence Handle10.1007/BF00058836 Occurrence Handle1368147

    Article  PubMed  Google Scholar 

  • H Solli SR Larter AG. Douglas (1980) Analysis of kerogens by pyrolysis-gas chromatography mass-spectrometry using selective ion monitoring. III AG Longchainalkylbenzenes. Douglas JR. Maxwell (Eds) Advances in Organic Geochemistry. Pergamon Press Oxford 591–597

    Google Scholar 

  • JG. Speight (1980) The Chemistry and Technology of Petroleum Marcel Dekker Inc New York

    Google Scholar 

  • B. Spiro (1984) ArticleTitleEffects of the mineral matrix on the distribution of geochemical markers in thermally affected sedimentary sequences Org Geochem 6 543–560 Occurrence Handle10.1016/0146-6380(84)90077-9

    Article  Google Scholar 

  • RE Summons TG. Powell (1987) ArticleTitleIdentification of aryl isoprenoids in source rocks and crude oils: biological markers from the green sulfur bacteria Geochim Cosmochim Acta 51 557–566 Occurrence Handle10.1016/0016-7037(87)90069-X

    Article  Google Scholar 

  • KI Suzuki K Saito A Kawaguchi S Okuda K. Komogata (1981) ArticleTitleOccurrence of ω-cyclohexyl fatty acids in curtobacterium pussilum strains J Gen Appl Microbiol 27 261–266

    Google Scholar 

  • H Takada R. Ishiwatari (1990) ArticleTitleBiodegradation experiments of linear alkylbenzenes (LABs): isomeric composition of C12 LABs as an indicator of the degree of LAB degradation in the aquatic environment Environ Sci Technol 24 86–91 Occurrence Handle10.1021/es00071a009

    Article  Google Scholar 

  • T Tange W Dhooge W. Verstraete (2000) ArticleTitleFormation of the metabolic intermediate 2,4,4-trimethyl-2-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol Biodegradation 11 9–11

    Google Scholar 

  • CJ. Thompson (1981) Identification of sulfur compounds in petroleum and alternative fossil fuels RK Freidlina AE. Skorova (Eds) Organic Sulfur Chemistry. Pergamon Press Oxford 189–208

    Google Scholar 

  • PW. Trudgill (1984) Microbial degradation of the alicyclic ring: structural relationship and metabolic pathways DT. Gibson (Eds) Microbial Degradation of Organic Compounds. Marcel Dekker New York 131–180

    Google Scholar 

  • FJ Weber KC Hage JAM. Bont Particlede (1995) ArticleTitleGrowth of the fungus Cladosporium sphaerospermum with toluene as the sole carbon and energy source Appl Environ Microbiol 61 3562–3566 Occurrence Handle7486990

    PubMed  Google Scholar 

  • JA Williams DL Dolcater BE Torkelson JC. Winters (1988) ArticleTitleAnomalous concentrations of specific alkylaromatic and alkylcycloparaffin components in West Texas and Michigan crude oils Org Geochem 13 47–60 Occurrence Handle10.1016/0146-6380(88)90024-1

    Article  Google Scholar 

  • Y Xinke F Pu RP. Philp (1990) ArticleTitleNovel biomarkers found in South Florida Basin Org Geochem 15 433–438 Occurrence Handle10.1016/0146-6380(90)90170-5

    Article  Google Scholar 

  • JS Yadav DL Lawrence BA Nuck TW Federle CA. Reddy (2001) ArticleTitleBiotransformation of linear alkylbenzene sulfonate (LAS) by Phanerochaete chrysosporium: oxidation of alkyl side-chain Biodegradation 12 443–453 Occurrence Handle10.1023/A:1015056530264 Occurrence Handle12051650

    Article  PubMed  Google Scholar 

  • GG Ying B Williams R. Kookana (2002) ArticleTitleEnvironmental fate of alkylphenols and alkylphenol ethoxylates – a review Environ Int 28 215–226 Occurrence Handle10.1016/S0160-4120(02)00017-X Occurrence Handle12222618

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Microbiology, Bose Institute, P-1/12 C.I.T. Scheme VII M, Kolkata, 700 054, India

    Tapan K. Dutta

Authors
  1. Tapan K. Dutta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tapan K. Dutta.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dutta, T.K. Origin, occurrence, and biodegradation of long-side-chain alkyl compounds in the environment: a review. Environ Geochem Health 27, 271–284 (2005). https://doi.org/10.1007/s10653-004-0158-0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10653-004-0158-0

Keywords

Search

Navigation