AFCDB: Phytosterol (FDB006298)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:04 UTC

Update date

2020-09-17 15:31:15 UTC

Primary ID

FDB006298

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phytosterol

Description

Beta-sitosterol, also known as sitosterol or harzol, 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. Beta-sitosterol is widely distributed in the plant kingdom and is a main dietary phytosterol (a plant sterol) found in vegetable oils, nuts, avocados and prepared foods, such as salad dressings. Phytopharmacological extracts, commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea, contain mixtures of phytosterols, that includes Beta-sitosterol. However, these extracts also contain some sterols bonded with glucosides. While beta-sitosterol is the purported active constituent, beta-sitosterol-beta-D-glucoside is often detected. Thus, one or both metabolites may be the active components. Phytosterols, like cholesterol, contain double bonds that are susceptible to oxidation. Beta-sitosterol may have anti-carcinogenic and anti-atherogenic properties (PMID: 13129445, 11432711). Benign prostatic hyperplasia patients treated with beta-sitosterol, compared with placebo, had improved urinary symptom scores and flow measures (PMID: 10368239). Hyperandrogenic postmenopausal women, with higher risk of breast cancer because of their endocrine profiles, were placed on a plant food-based diet, to determine if eating a plant-based diet, rich in phytosterols, rather than animal-based diet, would have an increase in serum phytosterols. Compared to controls, women placed on the plant-based diet had increased serum phytosterols, particularly beta-sitosterol, suggesting that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID: 14652381). Beta-sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID: 12579296). Although the exact mechanism of action of beta-sitosterols in the above studies is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism).

CAS Number

83-46-5

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	7.27	ALOGPS
logP	7.84	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	18.2	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	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C29H50O

IUPAC name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

InChI Identifier

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

Isomeric SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

Average Molecular Weight

414.718

Monoisotopic Molecular Weight

414.38616623

Classification

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

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:27693 )
phytosterols (CHEBI:27693 )
stigmastane (C01753 )
Stigmasterols and C24-ethyl derivatives (C01753 )
Stigmasterols and C24-ethyl derivatives (LMST01040129 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-052f-9821000000-0f43ba6def9281d5c86d	2015-03-01	View Spectrum
GC-MS	Phytosterol, 1 TMS, GC-MS Spectrum	splash10-054k-3912000000-22f633cd1bdd2ecca960	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-0aor-9810000000-ab4d6cb3490b23c5cb70	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-03di-5947700000-fe0573c7669e97c469f5	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-0002-2931000000-0d63e91b728deb1446a4	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9822000000-2be95863c114e7cd2597	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9601000000-edade780f6cfb8ddc7d1	Spectrum
GC-MS	Phytosterol, non-derivatized, GC-MS Spectrum	splash10-054k-3912000000-22f633cd1bdd2ecca960	Spectrum
Predicted GC-MS	Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052v-1109000000-2eef6dd56a6c52421610	Spectrum
Predicted GC-MS	Phytosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-4103900000-a09c1c265657e57bd096	Spectrum
Predicted GC-MS	Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phytosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phytosterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0002900000-f2b81675160568c483c5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05nb-3930100000-897e65b10be8a412585c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-6900000000-b62b8d1bd807fc41256b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0aor-9810000000-fcbfd841778e213b3d3e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-5947700000-4234b723ccdb0e25d290	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0002-2931000000-b2156fbd63c29312b076	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0a4l-9822000000-2be95863c114e7cd2597	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0019500000-b9eddfa8d56747167ada	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-5139100000-42d184a108f9e994dc01	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9076000000-54ef98673160128cbacd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-158617c2e43f1a46b58a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-632250471791929b07e3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2019000000-717c6229722cf73f3faa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-eda302082c5114b2ab3a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-86165feb8e32cd8692ad	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0001900000-1fc08db7654e3c4918f9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4117900000-f005f19377309e9fb82d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06du-9146100000-d28aeb2182048e0912fa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9511000000-ff6bd6e1f8902e32555d	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

26125

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

PHYTOSTEROL|PHYTOSTEROLS

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Phytosterol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti prostatotic			DUKE
hypocholesterolemic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Phytosterol (FDB006298)

Structure for FDB006298 (Phytosterol)