Structure Database (LMSD)

Common Name
Stigmastanol
Systematic Name
5α-stigmastan-3β-ol
Synonyms
  • Dihydro-sitosterol
  • Fucostanol
  • Stigmastanol
  • Stigmastane-3-beta-ol
  • Beta-Sitostanol
  • Dihydro-beta-sitosterol
LM ID
LMST01040266
Formula
C29H52O
Exact Mass
Calculate m/z
416.401815
Sum Composition
ST 29:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Stigmasterols and C24-ethyl derivatives [ST0104]

Biological Context

Sitostanol is a saturated sterol found in a variety of plants, including corn, wheat, and rice.1 It reduces cholesterol uptake in isolated rat jejunal loops when used at a concentration of 0.3 mM in a micellar solution containing cholesterol.2 Sitostanol decreases liver cholesterol levels and prevents abdominal aorta atheroma in rabbits when administered in a cholesterol-containing diet at 0.5%.3

This information has been provided by Cayman Chemical

References

1. Ikeda, I., Kawasaki, A., Samezima, K., et al. Antihypercholesterolemic activity of β-sitostanol in rabbits. J. Nutr. Sci. Vitaminol. (Tokyo) 27(3), 243-251 (1981).
2. Hassan, A.S., and Rampone, A.J. Effect of β-sitostanol (5 α-stigmastan-3 β-ol) on cholesterol absorption from micellar solutions in jejunal loops in situ. Steroids 36(6), 731-741 (1980).
3. Anderson, R.J., Nabsnhauer, F.P., and Shriner, R.L. The distribution of dihydrositosterol in plant fats. J. Biol. Chem. 71, 389-399 (1927).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Zea mays (#4577)
Magnoliopsida (#3398)
THE PHYTOSTEROLS OF THE ENDOSPERM OF CORN1,
J Am Chem Soc, 1927

String Representations

InChiKey (Click to copy)
LGJMUZUPVCAVPU-HRJGVYIJSA-N
InChi (Click to copy)
InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES (Click to copy)
C1C[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@H](C)CC[C@@H](CC)C(C)C)CC[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@H]1O

Other Databases

CHEBI ID
89400
PubChem CID
241572
Cayman ID
26094

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 469.61
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 8.39
Molar Refractivity 128.75

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Created at
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Updated at
25th Jul 2024