Cholestane

Cholestane
	; IUPAC numbering[1]
Names
	IUPAC name (8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	14982-53-7 5α/β ; 481-21-0 5α ; 481-20-9 5β ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:35516 ;
ChemSpider	5256870 ;
ECHA InfoCard	100.006.876
IUPHAR/BPS	2802;
PubChem CID	6857534;
	InChI InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1 Key: XIIAYQZJNBULGD-LDHZKLTISA-N ; InChI=1/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1 Key: XIIAYQZJNBULGD-LDHZKLTIBN;
	SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCCC4)C)C; C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)[C@H](C)CCCC(C)C)CC4)C;
Properties
Chemical formula	C27H48
Molar mass	372.68 g·mol−1
Density	0.911 g/ml
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Cholestane is a saturated 27-carbon tetracyclic triterpene. Cholestane, along with ergostane and stigmastane are used as biomarkers for early eukaryotic life^[2]. High abundance of cholestane relative to the others has been interpreted as the presence of rhodophytes^[3].

Derivatives of cholestane

Derivatives are classified in two families:

Sterols (with an alcohol group)
Cholestenes (with a double bond)

Some steroids, such as cholesterol, are both a sterol and a cholestene.

References

↑ The Nomenclature of Steroids, IUPAC
↑ Brocks, Jochen J.; Jarrett, Amber J. M.; Sirantoine, Eva; Hallmann, Christian; Hoshino, Yosuke; Liyanage, Tharika. "The rise of algae in Cryogenian oceans and the emergence of animals". Nature. 548 (7669): 578–581. doi:10.1038/nature23457.
↑ Summons, Roger E; Brassell, Simon C; Eglinton, Geoffrey; Evans, Evan; Horodyski, Robert J; Robinson, Neil; Ward, David M. "Distinctive hydrocarbon biomarkers from fossiliferous sediment of the Late Proterozoic Walcott Member, Chuar Group, Grand Canyon, Arizona". Geochimica et Cosmochimica Acta. 52 (11): 2625–2637. doi:10.1016/0016-7037(88)90031-2.

External links

Cholestanes at the US National Library of Medicine Medical Subject Headings (MeSH)

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[1] The Nomenclature of Steroids, IUPAC

[2] Brocks, Jochen J.; Jarrett, Amber J. M.; Sirantoine, Eva; Hallmann, Christian; Hoshino, Yosuke; Liyanage, Tharika. "The rise of algae in Cryogenian oceans and the emergence of animals". Nature. 548 (7669): 578–581. doi:10.1038/nature23457.

[3] Summons, Roger E; Brassell, Simon C; Eglinton, Geoffrey; Evans, Evan; Horodyski, Robert J; Robinson, Neil; Ward, David M. "Distinctive hydrocarbon biomarkers from fossiliferous sediment of the Late Proterozoic Walcott Member, Chuar Group, Grand Canyon, Arizona". Geochimica et Cosmochimica Acta. 52 (11): 2625–2637. doi:10.1016/0016-7037(88)90031-2.

Names

IUPAC numbering^[1]
IUPAC name (8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	14982-53-7 5α/β^Y 481-21-0 5α^Y 481-20-9 5β^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:35516^Y
ChemSpider	5256870^Y
ECHA InfoCard	100.006.876
IUPHAR/BPS	2802
PubChem CID	6857534
InChI InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1^Y Key: XIIAYQZJNBULGD-LDHZKLTISA-N^Y InChI=1/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1 Key: XIIAYQZJNBULGD-LDHZKLTIBN
SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCCC4)C)C C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)[C@H](C)CCCC(C)C)CC4)C
Properties
Chemical formula	C₂₇H₄₈
Molar mass	372.68 g·mol⁻¹
Density	0.911 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Cholestane

Derivatives of cholestane

See also

References

External links