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24:
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As it occurs within GDGT, biphytane has been detected in the water column, marine sediments, hydrothermally-influenced sediments, cold seep sediments dominated by anaerobic oxidation of methane activity, and limestone. Though it had been primarily studied in aquatic settings, recent studies have also
456:
measurements could be combined to further confirm the origin. Because methanotrophs utilize isotopically light carbon sources, they are characterized by very negative carbon isotope values (i.e. depleted in C). For example, by comparing δC values of biphytanic diacids and GDGT-derived biphytane from
448:
Biphytane is a well-established biomarker of archaea since it is found exclusively in archaea and all major groups except for halophilic
Archaea. When combined with other analyses, it could be used to gain further insight into the analyzed sample. For instance, the abundance ratio of the biphytane
336:
Glycerol dialkyl glycerol tetraethers (GDGT) are major membrane lipids synthesized by archaea and some bacteria. In particular, isoprenoid GDGTs are characterized by isoprenoid carbon chains connected to the glycerol molecules by ether bonds. Biphytane is produced by the chemical cleavage of the
344:
Biphytane can be found in cyclic forms containing one to three pentacyclic rings when derived from isoprenoid GDGTs with such biosynthetically cyclized isoprenoid carbon skeletons. In most analyzed samples from the environment, the acyclic form with biphytane as the isoprenoid carbon chain is
469:
sampled from the
Tisdale and Porcupine Assemblage (2,707 to 2685 Ma) near Timmins, ON, Canada. From the extracted samples, the authors measured biphytane, cyclic biphytanes, and derivatives of biphytanes. Because post-Archaean deposition of the compounds could be ruled out given the reduced
444:
Biphytane is considered to have a relatively high stability given its detection in high abundance within both recent and ancient sediments and petroleum, suggesting its ability to persist thermal maturation. Whether biphytane degrades to shorter isoprenoids over time remains unclear.
457:
the same seep limestones, a study inferred that, despite the chemical similarity of the compounds, they likely were derived from different sources; while the biphytanic diacids were mostly derived from methane-oxidizing euryarchea, the biphytanes were from mixed sources.
365:
environments with non-extreme pH and salinity have been available since the late 1970s. Because biphytane in particular has been widely detected in sties of active AOM activity, it is considered a biomarker of methanotrophic archaea.
393:
Typically, biphytane measurement is performed as an indirect analysis of GDGT. When chemically deriving biphytane from such ether lipids, the ether bonds are first cleaved using hydrogen iodide (HI), boron trichloride
354:
started investigating terrestrial environments, such as peat bogs where the source of biphytane was identified as methanogenic peat archaea. Studies have reported the detection of biphytane in petroleum as well.
449:(both acyclic and cyclic) to phytane has been used to distinguish between different groups of anaerobic methanotrophic archaea (ANME) from marine sediments given its higher abundance in ANME-1 than -2.
421:
Alternatively, direct analysis of GDGT can be done with liquid chromatography but, when further structural characterization is required, MS fragments characteristic of biphytane can be obtained via
389:
Mass spectral fragment ions characteristic of (acyclic) biphytane. Blue lines mark the location of fragmentation and the associated numbers correspond to the resulting ion fragments' m/z values.
436:
197, 259, 267, 323, 383, 393, and 463. Because the cyclic biphytanes yield different mass spectral fragment ions, the modified forms of biphytane present in a sample can be differentiated.
1167:
Ventura, Gregory T.; Kenig, Fabien; Reddy, Christopher M.; Schieber, Juergen; Frysinger, Glenn S.; Nelson, Robert K.; Dinel, Etienne; Gaines, Richard B.; Schaeffer, Philippe (2007-09-04).
86:
726:
Guo, Jinqiang; Yuan, Huamao; Song, Jinming; Qu, Baoxiao; Xing, Jianwei; Wang, Qidong; Li, Xuegang; Duan, Liqin; Li, Ning; Wang, Yingxia (2021-08-18).
188:
InChI=1S/C40H82/c1-11-33(3)19-13-21-35(5)23-15-25-37(7)27-17-29-39(9)31-32-40(10)30-18-28-38(8)26-16-24-36(6)22-14-20-34(4)12-2/h33-40H,11-32H2,1-10H3
373:
in eukaryotic membranes, GDGT plays a similar role in improving the rigidity of archaeal cell membranes. Supporting this, it has been reported that
470:
adsorptive capacity and restricted porosity of the sediments, the authors were able to conclude that the presence of biphytane, along with other
902:
Saito, Ryosuke; Kaiho, Kunio; Oba, Masahiro; Tong, Jinnan; Chen, Zhong-Qiang; Tian, Li; Takahashi, Satoshi; Fujibayashi, Megumu (2017-09-01).
204:
904:"Tentative identification of diagenetic products of cyclic biphytanes in sedimentary rocks from the uppermost Permian and Lower Triassic"
674:<663:cvardo>2.0.co;2 "δ13C values and radiocarbon dates of microbial biomarkers as tracers for carbon recycling in peat deposits"
415:
345:
typically the most abundant form. Hence, in this article, biphytane is used to refer to the acyclic form unless stated otherwise.
337:
ether bonds within isoprenoid GDGT (GDGT-0). It is composed of isoprene units bound by ether bonds with six isoprene units (or two
422:
1102:
297:
728:"Variation of Isoprenoid GDGTs in the Stratified Marine Water Column: Implications for GDGT-Based TEX86 Paleothermometry"
332:
Structures of biphytane with increasing degree of cyclization from top (acyclic) to bottom (with three cycloalkyl rings).
179:
1232:
556:"Distribution of acyclic and cyclic biphytanediols in recent marine sediments from IODP Site C0001, Nankai Trough"
402:) that produces alkyl halides. Then, the alkyl halides are either reduced to saturated hydrocarbons using HI/NaSCH
270:
853:
Damsté, Jaap S.Sinninghe; Schouten, Stefan; Hopmans, Ellen C.; van Duin, Adri C.T.; Geenevasen, Jan A.J. (2002).
361:
archaea, both indirect and direct evidence of GDGT originating from archaea of mesophilic marine environments or
414:. The obtained saturated or derivatized hydrocarbons can subsequently be separated and measured using standard
305:
697:
377:
increase the degree of cyclization with increasing growth temperatures to further improve membrane fluidity.
951:"An Overview of Lipid Biomarkers in Terrestrial Extreme Environments with Relevance for Mars Exploration"
143:
1014:
Blumenberg, Martin; Seifert, Richard; Reitner, Joachim; Pape, Thomas; Michaelis, Walter (2004-07-27).
903:
623:
555:
499:
300:(GDGT) degradation. As a common lipid membrane component, biphytane is widely used as a biomarker for
1169:"Molecular evidence of Late Archean archaea and the presence of a subsurface hydrothermal biosphere"
160:
426:
1124:
854:
324:
Molecular structures of isoprenoid GDGTs containing 0–4 cyclopentane rings (GDGT-0 to GDGT-4).
106:
775:
The biomarker guide: Volume 2, Biomarkers and isotopes in petroleum systems and earth history
36:
1089:, Encyclopedia of Earth Sciences Series, Dordrecht: Springer Netherlands, pp. 167–182,
1136:
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62:
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164:
8:
52:
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1031:
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966:
950:
919:
807:
689:
639:
571:
515:
500:"Evidence for anaerobic methane oxidation by archaea in euxinic waters of the Black Sea"
1203:
1168:
884:
835:
1058:
1015:
672:
Pancost, Richard D.; van Geel, Bas; Baas, Marianne; Sinninghe Damsté, Jaap S. (2000).
523:
1208:
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593:
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131:
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1125:"13C-depleted biphytanic diacids as tracers of past anaerobic oxidation of methane"
1090:
1053:
1035:
986:
970:
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811:
739:
693:
643:
624:"The organic geochemistry of glycerol dialkyl glycerol tetraether lipids: A review"
583:
575:
519:
471:
357:
While early studies had considered GDGTs (and hence biphytane) to be biomarkers of
227:
465:
In 2006, Ventura et al. measured solvent-extractable hydrocarbons with GC-MS from
385:
1094:
949:
Finkel, Pablo L.; Carrizo, Daniel; Parro, Victor; Sánchez-GarcĂa, Laura (2023).
815:
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264:
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1226:
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982:
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Schouten, Stefan; Hopmans, Ellen C.; Sinninghe Damsté, Jaap S. (2013-01-01).
597:
531:
498:
Schouten, Stefan; Wakeham, Stuart G; Damsté, Jaap S. Sinninghe (2001-10-01).
358:
1185:
1040:
1016:"Membrane lipid patterns typify distinct anaerobic methanotrophic consortia"
1212:
1067:
1000:
880:
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309:
974:
374:
312:
archaea. It has been found in both marine and terrestrial environments.
249:
97:
588:
293:
263:
Except where otherwise noted, data are given for materials in their
1123:
Birgel, Daniel; Elvert, Marcus; Han, Xiqiu; Peckmann, Jörn (2008).
671:
478:
sedimentary environments and in subsurface hydrothermal settings.
320:
773:
Peters, Kenneth E., Clifford C. Walters, and J. Michael
Moldowan.
85:
475:
338:
301:
118:
948:
453:
621:
370:
852:
432:
The diagnostic mass spectral fragment ions for biphytane are
75:
1013:
792:"Polar Lipids of Archaebacteria in Sediments and Petroleums"
304:. In particular, given its association with sites of active
148:
23:
1166:
698:
10.1130/0091-7613(2000)28<663:cvardo>2.0.co;2
212:
CCC(C)CCCC(C)CCCC(C)CCCC(C)CCC(C)CCCC(C)CCCC(C)CCCC(C)CC
1122:
789:
790:
Chappe, B.; Albrecht, P.; Michaelis, W. (1982-07-02).
497:
460:
1083:"Biomarkers (Organic, Compound-Specific Isotopes)"
901:
1224:
554:Saito, Hiroyuki; Suzuki, Noriyuki (2010-09-01).
474:, suggests the existence of archaea in the Late
130:
1173:Proceedings of the National Academy of Sciences
1020:Proceedings of the National Academy of Sciences
61:
1085:, in Reitner, Joachim; Thiel, Volker (eds.),
725:
439:
341:) linked together by a head-to-head linkage.
40:3,7,11,15,18,22,26,30-Octamethyldotriacontane
410:or converted to methylthioesthers with NaSCH
1080:
553:
163:
105:
1202:
1184:
1057:
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562:. Advances in Organic Geochemistry 2009.
380:
1081:Grice, Kliti; Brocks, Jochen J. (2011),
384:
327:
319:
308:(AOM), it is considered a biomarker of
159:
1225:
423:high-performance liquid chromatography
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1160:
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315:
191:Key: WEHKMXJXZKAYRJ-UHFFFAOYSA-N
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416:gas chromatography-mass spectrometry
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298:glycerol dialkyl glycerol tetraether
777:. Cambridge University Press, 2007.
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461:Case study: Late Archean sediments
14:
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780:
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662:
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1149:10.1016/j.orggeochem.2007.08.013
928:10.1016/j.orggeochem.2017.04.013
648:10.1016/j.orggeochem.2012.09.006
580:10.1016/j.orggeochem.2010.05.007
239:
22:
1116:
1074:
1007:
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267:(at 25 °C , 100 kPa).
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306:anaerobic oxidation of methane
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1:
524:10.1016/S0146-6380(01)00110-3
481:
1095:10.1007/978-1-4020-9212-1_29
7:
816:10.1126/science.217.4554.65
732:Frontiers in Marine Science
398:), or boron tribromide (BBr
10:
1249:
1087:Encyclopedia of Geobiology
872:10.1194/jlr.M200148-JLR200
440:Application as a biomarker
859:Journal of Lipid Research
745:10.3389/fmars.2021.715708
261:
220:
200:
175:
45:
35:
30:
21:
427:tandem mass spectrometry
1233:Terpenes and terpenoids
1186:10.1073/pnas.0610903104
1041:10.1073/pnas.0401188101
390:
381:Measurement techniques
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325:
975:10.1089/ast.2022.0083
467:metasedimentary rocks
388:
331:
323:
1129:Organic Geochemistry
908:Organic Geochemistry
628:Organic Geochemistry
560:Organic Geochemistry
504:Organic Geochemistry
418:(GC-MS) procedures.
1179:(36): 14260–14265.
1141:2008OrGeo..39..152B
1032:2004PNAS..10111111B
1026:(30): 11111–11116.
967:2023AsBio..23..563F
920:2017OrGeo.111..144S
808:1982Sci...217...65C
690:2000Geo....28..663P
640:2013OrGeo..54...19S
572:2010OrGeo..41.1001S
516:2001OrGeo..32.1277S
257: g/mol
18:
391:
334:
326:
316:Chemical structure
271:Infobox references
16:
1104:978-1-4020-9212-1
865:(10): 1641–1651.
510:(10): 1277–1281.
472:molecular fossils
349:Biological origin
279:Chemical compound
277:
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144:CompTox Dashboard
87:Interactive image
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1135:(1): 152–156.
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961:(5): 563–604.
941:
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855:"Crenarchaeol"
845:
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661:
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429:(HPLC-MS/MS).
411:
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310:methanotrophic
296:produced from
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46:Identifiers
914:: 144–153.
221:Properties
1110:2023-05-20
684:(7): 663.
589:2115/47336
482:References
425:linked to
363:lacustrine
294:isoprenoid
287:bisphytane
250:Molar mass
98:ChemSpider
74:3D model (
63:84296-10-6
53:CAS Number
37:IUPAC name
17:Biphytane
1195:0027-8424
1050:0027-8424
983:1531-1074
936:0146-6380
889:219230652
824:0036-8075
754:2296-7745
706:0091-7613
656:0146-6380
634:: 19–61.
598:0146-6380
532:0146-6380
283:Biphytane
1227:Category
1213:17726114
1068:15258285
1001:36880883
992:10150655
881:12364548
840:42758483
832:17739984
406:or LiAlH
339:phytanes
289:) is a C
132:13797360
107:57509546
1204:1964827
1137:Bibcode
1028:Bibcode
963:Bibcode
916:Bibcode
804:Bibcode
796:Science
686:Bibcode
678:Geology
636:Bibcode
568:Bibcode
512:Bibcode
476:Archean
371:sterols
302:archaea
255:565.112
119:PubChem
1211:
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1066:
1059:503748
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596:
530:
205:SMILES
31:Names
885:S2CID
836:S2CID
180:InChI
76:JSmol
1209:PMID
1191:ISSN
1099:ISBN
1064:PMID
1046:ISSN
997:PMID
979:ISSN
932:ISSN
877:PMID
828:PMID
820:ISSN
750:ISSN
702:ISSN
652:ISSN
594:ISSN
528:ISSN
394:(BCl
285:(or
1199:PMC
1181:doi
1177:104
1145:doi
1091:doi
1054:PMC
1036:doi
1024:101
987:PMC
971:doi
924:doi
912:111
867:doi
812:doi
800:217
740:doi
694:doi
644:doi
584:hdl
576:doi
520:doi
434:m/z
149:EPA
122:CID
1229::
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1171:.
1157:^
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1133:39
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