AFCDB: beta-Sitosterol (FDB012362)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:08 UTC

Update date

2019-11-26 03:06:38 UTC

Primary ID

FDB012362

Secondary Accession Numbers

FDB031179
FDB006298

Chemical Information

FooDB Name

beta-Sitosterol

Description

beta-Sitosterol, also known as sitosterol or a-phytosterol, 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. Thus, beta-sitosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on beta-Sitosterol.

CAS Number

83-46-5

Structure

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

Synonyms

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

Physiological effect

Health effect:

Health condition:

Short bowel syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 83.99%; H 12.15%; O 3.86%	DFC
Melting Point	Mp 136-137°	DFC
Optical Rotation	[a]22D -35 (CHCl3)	DFC

Showing 1 to 10 of 14 entries

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

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00852

CRC / DFC (Dictionary of Food Compounds) ID

CBR05-M:HGN93-D

EAFUS ID

Not Available

Dr. Duke ID

SITOSTEROL|BETA-SITOSTEROL

BIGG ID

Not Available

KNApSAcK ID

C00023770

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

Beta-Sitosterol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00003672

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
androgenic			DUKE
angiogenic	50927	An agent that induces or stimulates the physiologic angiogenesis process.	DUKE
anorexic	50780	An agent which regulates the physiologic mechanisms that control the appetite and food intake.	DUKE
anti adenomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti androgenic	35497	A compound which inhibits or antagonises the biosynthesis or actions of androgens.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti edemic			DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti feedant			DUKE

Showing 1 to 10 of 42 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

beta-Sitosterol (FDB012362)

Structure for FDB012362 (beta-Sitosterol)