ContaminantDB: Stigmastanol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:11:43 UTC

Update Date

2026-03-26 20:35:37 UTC

Accession Number

CHEM023631

Identification

Common Name

Stigmastanol

Class

Small Molecule

Description

Stigmastanol, also known as sitostanol or (3b)-stigmastan-3-ol, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Stigmastanol can be found primarily in blood and feces, as well as in human skeletal muscle tissue. Stigmastanol can be found anywhere throughout the human cell, such as in in the peroxisome, in the cytoplasm, in the Golgi apparatus, and in the membrane (predicted from logP). It can also be found in the extracellular space. Moreover, stigmastanol is found to be associated with sitosterolemia, an inborn error of metabolism. Stigmastanol (sitostanol) is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmastanol inhibits the absorption of cholesterol from the diet. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver (Wikipedia). Stigmastanol is plant stanol. It can decrease the circulating LDL-cholesterol level by reducing intestinal cholesterol absorption (PMID 16910223).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dihydrositosterol	MeSH
24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol	MeSH
beta-Sitostanol	MeSH
Sitostanol	MeSH
Stigmastanol, (3beta,5beta,24S)-isomer	MeSH
24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol	MeSH
(3b)-Stigmastan-3-ol	HMDB
(3beta)-Stigmastan-3-ol	HMDB
(3beta,5alpha)-Stigmastan-3-ol	HMDB
24-alpha-Ethylcholestanol	HMDB
24a-Ethylcholestanol	HMDB
4a-Methyl-5a,14a-lumistan-3b-ol	HMDB
4a-Methylcampestanol	HMDB
5,6-dihydro-b-Sitosterol	HMDB
5,6-dihydro-beta-Sitosterol	HMDB
5a-Stigmastan-3b-ol	HMDB
5alpha-Stigmastan-3beta-ol	HMDB
b-Sitostanol	HMDB
beta-dihydro-Sitosterol	HMDB
dihydro-b-Sitosterol	HMDB
dihydro-beta-Sitosterol	HMDB
Dihydrositosterin	HMDB
Fucostanol	HMDB
Spinastanol	HMDB
Stigmastan-3-ol	HMDB
Stigmastane-3-beta-ol	HMDB
Stigmastanol	MeSH

Chemical Formula

C₂₉H₅₂O

Average Molecular Mass

416.723 g/mol

Monoisotopic Mass

416.402 g/mol

CAS Registry Number

83-45-4

IUPAC Name

(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

Traditional Name

stigmastane-3-β-ol

SMILES

CCC(CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C)C(C)C

InChI Identifier

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

InChI Key

LGJMUZUPVCAVPU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
C24-propyl-sterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.1e-05 g/L	ALOGPS
logP	7.23	ALOGPS
logP	8.25	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.92 m³·mol⁻¹	ChemAxon
Polarizability	54.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-066u-4942100000-604c3357e69c5eff6d37	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066u-4942100000-604c3357e69c5eff6d37	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-2109200000-a86730d94764ca5efe85	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3103900000-2af97f9cf8a2adff3196	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0019600000-d66897ecdbe2fe845508	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-4149200000-b304e7e4678a4df85f02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-8089100000-404a21c90ecdfcc88b6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0002900000-5b14a67727dfd30debe9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0004900000-af8991b83701d4b9f081	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0012-1009000000-eebc7b9b36cf260dbceb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-b5f23f2410b0642246b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000900000-bb6fb31d418e3fc0bd50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02ta-0004900000-0b0cca9041a827eb2238	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2125900000-88705afd06ff3d3ec277	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9022300000-71d6fc93ae624cc61e6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9610000000-0304da0e562e0b20612f	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum