Crocetane: Difference between revisions

Crocetane
Names
	IUPAC name 2,6,11,15-Tetramethylhexadecane
Identifiers
CAS Number	504-44-9;
3D model (JSmol)	Interactive image;
ChemSpider	12006 ;
EC Number	211-332-2;
PubChem CID	136331;
CompTox Dashboard (EPA)	DTXSID80964656 ;
	InChI InChI=1S/C20H42/c1-17(2)11-9-15-19(5)13-7-8-14-20(6)16-10-12-18(3)4/h17-20H,7-16H2,1-6H3 Key: KKFZXXATNGJPJS-UHFFFAOYSA-N ;
	SMILES CC(C)CCCC(C)CCCCC(C)CCCC(C)C;
Properties
Chemical formula	C20H42
Molar mass	282.556 g·mol−1
Related compounds
Related alkanes	Phytane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Crocetane, or 2,6,11,15-tetramethylhexadecane, is an isoprenoid hydrocarbon compound. Unlike its isomer phytane, crocetane has a tail-to-tail linked carbon skeleton. Crocetane has been detected in modern sediments and geological records as a biomarker, often associated with anaerobic methane oxidation.

Research

Crocetane was first studied^[2] in the late 1920s and early 1930s for the structural identification of crocetin, which is its polyunsaturated diacid analogue. The infrared spectrum was reported in 1950^[3], the mass spectrum was described in 1968^[4] and the ¹H and ¹³C NMR spectra was obtained in 1990s.^[2]

In 1994, Liangqiao Bian^[5] first reported strong ¹³C depletion in crocetane from anoxic sediments in the Kattegat. Such low ¹³C content is thought to originate from microbes harvesting biogenic methane, which is always ¹³C depleted^[6], as a carbon source. Several groups made similar observations in either modern or ancient sediments near methane seeps. Crocetane was found in environments with anaerobic methane oxidizng consortium, comprised of methanotrophic archea and sulfate-reducing bacteria. These work makes crocetane the first biomarker^[7] of anaerobic methanotrophy.

Analysis Techniques

Due to structural similarities, chromatographic speration of crocetane and phytane is difficult. Specific columns, such as

^ "Hexadecane, 2,6,11,15-tetramethyl-". webbook.nist.gov.
^ ^a ^b Robson, J. N.; Rowland, S. J. (1993-09-01). "Synthesis, chromatographic and spectral characterisation of 2,6,11,15-tetramethylhexadecane (crocetane) and 2,6,9,13-tetramethyltetradecane: reference acyclic isoprenoids for geochemical studies". Organic Geochemistry. 20 (7): 1093–1098. doi:10.1016/0146-6380(93)90117-T.
^ Pliva, Josef; Sorensen, Andreas (1950). "Studies Related to Pristane: IV. InfraRed Spectra" (PDF). ACTA CHEMICA SCANDINAVICA. 4: 846–849.
^ McCarthy, E. D.; Han, Jerry; Calvin, Melvin (1968-08-01). "Hydrogen atom transfer in mass spectrometric fragmentation patterns of saturated aliphatic hydrocarbons". Analytical Chemistry. 40 (10): 1475–1480. doi:10.1021/ac60266a021. ISSN 0003-2700.
^ Bian, Liangqiao (1994). "Isotopic biogeochemistry of individual compounds in a modern coastal marine sediment (Kattegat, Denmark and Sweden)". M.Sc. thesis. Dept. of Geological Sciences, Univ. Indiana.
^ Whiticar, Michael J. (1999-09-30). "Carbon and hydrogen isotope systematics of bacterial formation and oxidation of methane". Chemical Geology. 161 (1–3): 291–314. doi:10.1016/S0009-2541(99)00092-3.
^ Hinrichs, K.-U.; Boetius, A. (2002-01-01). Wefer, Professor Dr Gerold; Billett, Dr David; Hebbeln, Dr Dierk; Jørgensen, Professor Dr Bo Barker; Schlüter, Professor Dr Michael; Weering, Dr Tjeerd C. E. van (eds.). Ocean Margin Systems. Springer Berlin Heidelberg. pp. 457–477. doi:10.1007/978-3-662-05127-6_28. ISBN 9783642078729.

[NIST-1] "Hexadecane, 2,6,11,15-tetramethyl-". webbook.nist.gov.

[Robson_1993-2] Robson, J. N.; Rowland, S. J. (1993-09-01). "Synthesis, chromatographic and spectral characterisation of 2,6,11,15-tetramethylhexadecane (crocetane) and 2,6,9,13-tetramethyltetradecane: reference acyclic isoprenoids for geochemical studies". Organic Geochemistry. 20 (7): 1093–1098. doi:10.1016/0146-6380(93)90117-T.

[3] Pliva, Josef; Sorensen, Andreas (1950). "Studies Related to Pristane: IV. InfraRed Spectra" (PDF). ACTA CHEMICA SCANDINAVICA. 4: 846–849.

[4] McCarthy, E. D.; Han, Jerry; Calvin, Melvin (1968-08-01). "Hydrogen atom transfer in mass spectrometric fragmentation patterns of saturated aliphatic hydrocarbons". Analytical Chemistry. 40 (10): 1475–1480. doi:10.1021/ac60266a021. ISSN 0003-2700.

[5] Bian, Liangqiao (1994). "Isotopic biogeochemistry of individual compounds in a modern coastal marine sediment (Kattegat, Denmark and Sweden)". M.Sc. thesis. Dept. of Geological Sciences, Univ. Indiana.

[6] Whiticar, Michael J. (1999-09-30). "Carbon and hydrogen isotope systematics of bacterial formation and oxidation of methane". Chemical Geology. 161 (1–3): 291–314. doi:10.1016/S0009-2541(99)00092-3.

[7] Hinrichs, K.-U.; Boetius, A. (2002-01-01). Wefer, Professor Dr Gerold; Billett, Dr David; Hebbeln, Dr Dierk; Jørgensen, Professor Dr Bo Barker; Schlüter, Professor Dr Michael; Weering, Dr Tjeerd C. E. van (eds.). Ocean Margin Systems. Springer Berlin Heidelberg. pp. 457–477. doi:10.1007/978-3-662-05127-6_28. ISBN 9783642078729.

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