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S1270

Sigma-Aldrich

β-Sitosterol

synthetic, ≥95%

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Synonym(s):
beta-Sitosterol, α-Dihydrofucosterol, 22,23-Dihydrostigmasterol, 24α-Ethylcholesterol, 5-Stigmasten-3β-ol
Empirical Formula (Hill Notation):
C29H50O
CAS Number:
Molecular Weight:
414.71
Beilstein/REAXYS Number:
1916165
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

assay

≥95%

form

powder

mp

136-140 °C (lit.)

functional group

hydroxyl

shipped in

ambient

storage temp.

−20°C

SMILES string

O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CC[C@H](C(C)C)CC

InChI

1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI key

KZJWDPNRJALLNS-VJSFXXLFSA-N

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1 of 4

This Item
854515671521612947
vibrant-m

S1270

β-Sitosterol

vibrant-m

85451

β-Sitosterol

vibrant-m

567152

β-Sitosterol

vibrant-m

1612947

β-Sitosterol

biological source

synthetic

biological source

plant

biological source

-

biological source

-

functional group

hydroxyl

functional group

hydroxyl

functional group

-

functional group

-

mp

136-140 °C (lit.)

mp

136-140 °C (lit.)

mp

-

mp

136-140 °C (lit.)

shipped in

ambient

shipped in

-

shipped in

ambient

shipped in

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

-

Application

β-Sitosterol has been used:
  • to study its ability to improve the suitability of two pollens
  • as a standard in the determination of sterol purities
  • as a standard in quantitative genetic analysis
  • as a standard in the estimation of plant sterols

Biochem/physiol Actions

A phytosterol with structure very similar to cholesterol that exhibits estrogenic activity. Inhibits proliferation of human leukemia cells, with G2/M arrest, endoreduplication, and polymerization of α-tubulin and microtubules.
Increased β-sitosterol administration displaces cholesterol during absorption. This elevates fecal secretion. It is known to regulate intestinal immunity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Polymeric Biomaterials: Medicinal and Pharmaceutical Applications, 2, 162-162 (2013)
Essence of Anesthesia Practice E-Book, 657-657 (2010)
Dong-Oh Moon et al.
Cancer letters, 264(2), 181-191 (2008-03-04)
beta-Sitosterol (SITO) is a potentially valuable candidate for cancer chemotherapy, however the cellular and molecular mechanisms responsible for its anti-cancer activity are unknown. Therefore, we attempted to elucidate the mechanisms responsible for SITO-induced anti-proliferation in human leukemia cells. Treatment with
Sterol limitation in a pollen-fed omnivorous lady beetle (Coleoptera: Coccinellidae)
Pilorget L, et al.
Journal of Insect Physiology, 56(1), 81-87 (2010)
Using theoretical correction factors for quantitative analysis of sterols and sterol concentrates
Costin CD, et al.
Journal of the American Oil Chemists' Society, 86(2), 111-118 (2009)

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