Brassicasterol

Chemical compound From Wikipedia, the free encyclopedia

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).

Quick facts Names, Identifiers ...
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 Â°C (302 to 304 Â°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 Â°C [77 Â°F], 100 kPa).
☒N verify (what is checkY☒N ?)
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There is some evidence to suggest that it may also be a relevant additional biomarker in Alzheimer's disease. More specifically, AD patients have lower levels of this sterol in their cerebrospinal fluid.[1]

Chemical properties

Solubility

Brassicasterol has a low water solubility and, as a consequence, a high octanol-water partition coefficient. This means that, in most environmental systems, brassicasterol will be associated with the solid phase.

Degradation

In anaerobic sediments and soils, brassicasterol is stable for many hundreds of years, enabling it to be used as an indicator of past algal production (see below).

Formation and occurrences

It can be found in Mirabilis jalapa.[2]

Algal sources

Brassicasterol is formed in plants from the isoprenoid squalene through campesterol as an intermediate. A list of the algae in which brassicasterol has been identified is shown below together with approximate composition.[3][4]

More information Species, A ...
Sterol content of selected dinoflagellates (as percentage). Data from Volkman, 1986
Species A B C D E F G H others
Gonyaulax spp10000000000
Peridinium foliaceum10000000000
Peridinium foliaceum80200000000
Gonyaulax diegensis390000002932
Pyrocystis lunula76602100015
Gonyaulax polygramma36109700047
Gymnodinium wilczeki263903510000
Glenodinium hallii85000042000
Noctiluca milaris01157306014
Gymnodinium simplex00005300047
Prorocentrum cordatum70005063025
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A = cholesterol
B = campesterol
C = sitosterol
D = 22-dehydrocholesterol ((22E)-cholesta-5,22-dien-3β-ol)
E = brassicasterol
F = stigmasterol
G = 24-methylene cholesterol
H = fucosterol

Use as a tracer for marine algae

The principal source of brassicasterol in the environment is from marine algae. Its relatively high concentration and stability allows it to be used in the assessment of the origin of organic matter in samples, especially sediments.

References

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