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F5379

Sigma-Aldrich

Fucosterol

≥93%, powder, antioxidant

Synonym(s):

3β-Hydroxy-5,24(28)-stigmastadiene, 5,24(28)-Stigmastadien-3β-ol

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About This Item

Empirical Formula (Hill Notation):
C29H48O
CAS Number:
17605-67-3
Molecular Weight:
412.69
MDL number:
MFCD00037543
UNSPSC Code:
41116107
PubChem Substance ID:
24894886
NACRES:
NA.77

product name

Fucosterol, ≥93%

Assay

≥93%

storage temp.

2-8°C

SMILES string

C\C=C(/CC[C@H](C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C

InChI

1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+

InChI key

OSELKOCHBMDKEJ-QPSGOUHRSA-N

General description

Fucosterol is a phytosterol abundantly present in algae, Ecklonia arborea and Silvetia compressa.

Application

Fucosterol has been used:
  • as an environmental contaminant to study its effect on morphological development in growing zebrafish embryos and larvae
  • to study its anxiolytic effects in mice
  • as an external standard to analyze sterols in seaweed samples

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cassandra D Kinch et al.
Aquatic toxicology (Amsterdam, Netherlands), 175, 286-298 (2016-04-24)
Exposure to environmental contaminants has been linked to developmental and reproductive abnormalities leading to infertility, spontaneous abortion, reduced number of offspring, and metabolic disorders. In addition, there is evidence linking environmental contaminants and endocrine disruption to abnormal developmental rate, defects
A Kamal-Eldin et al.
Lipids, 33(11), 1073-1077 (1998-12-31)
This work shows that fucosterol, delta5-avenasterol, and similar ethylidene-side chain sterols can undergo acid-catalyzed isomerization to give a mixture of five isomers. Four isomers formed from fucosterol were analyzed, using gas chromatography-mass spectrometry, and were characterized as delta5-avenasterol, two delta5,23-stigmastadienols
Nicolas Panayotis et al.
Cell reports. Medicine, 2(5), 100281-100281 (2021-06-08)
Anxiety and stress-related conditions represent a significant health burden in modern society. Unfortunately, most anxiolytic drugs are prone to side effects, limiting their long-term usage. Here, we employ a bioinformatics screen to identify drugs for repurposing as anxiolytics. Comparison of
I Ikeda et al.
Journal of lipid research, 29(12), 1573-1582 (1988-12-01)
The extent and site(s) of inhibition of cholesterol absorption by plant sterols, sitosterol and fucosterol, were studied in rats. The intragastric administration of a single emulsified lipid meal containing 25 mg [3H]cholesterol and 25 mg of either sitosterol or fucosterol
J H Sheu et al.
Journal of natural products, 62(2), 224-227 (1999-03-17)
Fucosterol (1), 24xi-hydroperoxy-24-vinylcholesterol (2), 29-hydroperoxystigmasta-5,24(28)-dien-3beta-ol (3), 24-ethylcholesta-4,24(28)-dien-3-one (4), 24xi-hydroperoxy-24-ethylcholesta-4,28(29)-dien-3-one (5), 24-ethylcholesta-4,24(28)-dien-3,6-dione (6), 24xi-hydroperoxy-24-ethylcholesta-4,28(29)-dien-3,6-di one (7), 6beta-hydroxy-24-ethylcholesta-4,24(28)-dien-3-one (8), and 24xi-hydroperoxy-6beta-hydroxy-24-ethylcholesta-4,28(2 9)-dien-3-one (9) were isolated from the marine brown alga Turbinaria conoides. The structures of these compounds were established by spectral analysis.
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