Crenarchaeol

Crenarchaeol
Names
IUPAC name
[(9S,12S,16S,24S,28R,31R,35S,43S,46S,50S,58S,62R,65R)-12-(Hydroxymethyl)-9,16,24,28,31,35,43,50,58,62,65-undecamethyl-11,14,45,48-tetraoxahexacyclo[63.3.1.12,5.120,23.136,39.154,57]triheptacontan-46-yl]methanol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C82H154O6/c1-61-20-12-27-68(8)75-41-37-71(48-75)30-15-23-64(4)56-86-60-

    81(54-84)88-58-67(7)26-18-33-74-40-44-78(51-74)79-34-19-46-82(11,52-79)47-45-63( 3)22-14-29-70(10)77-42-38-72(49-77)31-16-24-65(5)55-85-59-80(53-83)87-57-66(6)25 -17-32-73-39-43-76(50-73)69(9)28-13-21-62(2)36-35-61/h61-81,83-84H,12-60H2,1-11H 3/t61-,62-,63-,64+,65+,66+,67+,68+,69+,70+,71?,72?,73?,74?,75?,76?,77?,78?,79?,8

    0+,81+,82-/m1/s1
    Key: VLTNDASRNRVJQP-VFMBZWNMSA-N
  • C[C@@H]1CCC[C@@H](C2CCC(C2)CCC[C@@H](COC[C@@H](OC[C@H](CCCC3CCC(C3)C4CCC[C@@](C4)(CC[C@@H](CCC[C@@H](C5CCC(C5)CCC[C@@H](COC[C@@H](OC[C@H](CCCC6CCC(C6)[C@H](CCC[C@H](CC1)C)C)C)CO)C)C)C)C)C)CO)C)C
Properties
C82H154O6
Molar mass 1236.128 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Crenarchaeol is a glycerol biphytanes glycerol tetraether (GDGT) biological membrane lipid. Together with archaeol, crenarcheol comprises a major component of archaeal membranes.[1] Archaeal membranes are distinct from those of bacteria and eukaryotes because they contain isoprenoid GDGTs instead of diacyl lipids, which are found in the other domains (bacteria, procarya). It has been proposed that GDGT membrane lipids are an adaptation to the high temperatures present in the environments that are home to extremophile archaea [2]

  1. ^ Caforio, Antonella; Driessen, Arnold J.M. (2017). "Archaeal phospholipids: Structural properties and biosynthesis" (PDF). Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1862 (11): 1325–1339. doi:10.1016/j.bbalip.2016.12.006. PMID 28007654.
  2. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).