Brassicasterol

Brassicasterol
Brassicasterol
Ball-and-stick model of brassicasterol
Names
IUPAC name
Ergosta-5,22-dien-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,3E,4R)-5,6-Dimethylhept-3-en-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Other names
brassicasterol
(3β,22E)-ergosta-5,22-dien-3-ol
24β-methylcholesta-5,22-dien-3 beta-ol
24-methyl cholest-5,22-dien-3β-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.807 Edit this at Wikidata
UNII
  • InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1 checkY
    Key: OILXMJHPFNGGTO-ZAUYPBDWSA-N checkY
  • InChI=1/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
    Key: OILXMJHPFNGGTO-ZAUYPBDWBS
  • O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@@]2([C@H](CC[C@@H]12)[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4
Properties
C28H46O
Molar mass 398.675 g·mol−1
Appearance White solid
Melting point 150 to 151 °C (302 to 304 °F; 423 to 424 K)
Hazards
Flash point Non-flammable
Related compounds
Related Sterols
 cholesterol
β-sitosterol
campesterol
stigmasterol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Brassicasterol (24-methyl cholest-5,22-dien-3β-ol) is a 28-carbon sterol synthesised by several unicellular algae (phytoplankton) and some terrestrial plants, like rape. This compound has frequently been used as a biomarker for the presence of (marine) algal matter in the environment, and is one of the ingredients in stigmasterol-rich plant sterols (Number E499 in the European numbering system). There is some evidence to suggest that it may also be a relevant additional biomarker in Alzheimer's disease.[1]

  1. ^ Vanmierlo, T.; Popp, J.; Kölsch, H.; Friedrichs, S.; Jessen, F.; Stoffel-Wagner, B.; Bertsch, T.; Hartmann, T.; Maier, W.; von Bergmann, K.; Steinbusch, H.; Mulder, M.; Lütjohann, D. (September 2011). "The plant sterol brassicasterol as additional CSF biomarker in Alzheimer's disease: Plant sterols as biomarker in AD". Acta Psychiatrica Scandinavica. 124 (3): 184–192. doi:10.1111/j.1600-0447.2011.01713.x. PMID 21585343. S2CID 25346711.