Showing Compound Stigmasterol (FDB001936)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:10 UTC

Update date

2025-11-18 22:33:52 UTC

Primary ID

FDB001936

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Stigmasterol

Description

Stigmasterol, also known as poriferasterol or 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. Stigmasterol is a phytosterol, meaning it is steroid derived from plants. ,It is very hydrophobic, practically insoluble in water, and relatively neutral. Stigmasterol is among the most abundant of plant sterols with its major function being to maintain the structure and physiology of cell membranes. It is found in plant fats or oils associated with various vegetables, legumes, nuts, and seeds such as¬†soybean,¬†calabar bean, rape seed and various herbs. Stigmasterol is also a constituent of unpasteurized milk. Pasteurization is known to inactivate stigmasterol. Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Consumption of 2 grams per day of plant sterols is associated with a reduction in blood LDL cholesterol of 8-10% (PMID: 29267628). As the typical western diet contains only about 300 mg/day of phytosterols, foods enriched with phytosterols are usually used to achieve the recommended intake (PMID: 29267628). The mechanism behind phytosterols lowering cholesterol involves the inhibition of the incorporation of cholesterol into micelles in the gastrointestinal tract, which decreases the overall amount of cholesterol absorbed. This may in turn help to control body total plasma cholesterol levels, as well as modify HDL, LDL and TAG levels in blood. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people wishing to lower their cholesterol levels. More recently, stigmasterol has been identified as a potent and independent risk factor for cardiovascular disease. Accumulation of stigmasterol leads to left ventricle dysfunction, cardiac interstitial fibrosis and macrophage infiltration without atherosclerosis (PMID: 30675518). Stigmasterol has been found to be associated with phytosterolemia, a disease characterized by elevated levels of dietary plant sterols in the blood. (PMID: 30675518).

CAS Number

83-48-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3beta,22E)-Stigmasta-5,22-dien-3-ol	ChEBI
5,22-Cholestadien-24-ethyl-3beta-ol	ChEBI
beta-Stigmasterol	ChEBI
Phytosterol	ChEBI
Poriferasterol	ChEBI
Stigmasta-5,22-dien-3beta-ol	ChEBI
(3b,22E)-Stigmasta-5,22-dien-3-ol	Generator
(3β,22E)-Stigmasta-5,22-dien-3-ol	Generator
5,22-Cholestadien-24-ethyl-3b-ol	Generator
5,22-Cholestadien-24-ethyl-3β-ol	Generator
b-Stigmasterol	Generator
β-Stigmasterol	Generator
Stigmasta-5,22-dien-3b-ol	Generator
Stigmasta-5,22-dien-3β-ol	Generator
(24S)-5,22-Stigmastadien-3b-ol	HMDB
17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
Stigmasta-5,22-dien-3-b-ol	HMDB
Stigmasta-5,22-dien-3-beta-ol	HMDB
Stigmasterin	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3beta-ol	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3β-ol	HMDB
(24S)-5,22-Stigmastadien-3beta-ol	HMDB
(24S)-5,22-Stigmastadien-3β-ol	HMDB
(24S)-Stigmast-5,22-dien-3beta-ol	HMDB
(24S)-Stigmast-5,22-dien-3β-ol	HMDB
24-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24-Ethyl-5,22-cholestadien-3β-ol	HMDB
24beta-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24β-Ethyl-5,22-cholestadien-3β-ol	HMDB
Stigmasta-5,22(E)-dien-3beta-ol	HMDB
Stigmasta-5,22(E)-dien-3β-ol	HMDB
Stigmasterol	HMDB
delta5,22-Stigmastadien-3beta-ol	HMDB
delta5-Stigmasterol	HMDB
Δ5,22-Stigmastadien-3β-ol	HMDB
Δ5-Stigmasterol	HMDB
(22E)-Stigmasta-5,22-dien-3-ol	biospider
(22E)-Stigmasta-5,22-dien-3beta-ol	biospider
(24S)-5,22-Stigmastadien-3β-ol	biospider
(24S)-5,22-stigmastadien-3b-ol	biospider
β-Stigmasterol	biospider
D5-Stigmasterol	biospider
Delta5-Stigmasterol	biospider
Delta5,22-Stigmastadien-3beta-ol	biospider
Serposterol	db_source
Stigmasta-5,22-dien-3-ol, (3β,22E)-	biospider
Stigmasta-5,22-dien-3-ol, (3β)-	biospider
Stigmasta-5,22-dien-3-ol, (3beta,22E)- (9CI)	biospider
Stigmasta-5,22-dien-3-ol, (3beta)-	biospider
Stigmasta-5,22-dien-3β-ol	biospider
Stigmasta-5,22-dien-3beta-ol (8CI)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	2.7e-05 g/L	ALOGPS
logP	6.95	ALOGPS
logP	7.48	ChemAxon
logS	-7.2	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	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	53.55 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	No	ChemAxon

Chemical Formula

C29H48O

IUPAC name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

InChI Identifier

InChI=1S/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

HCXVJBMSMIARIN-PHZDYDNGSA-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)\C=C\[C@@H](CC)C(C)C

Average Molecular Weight

412.702

Monoisotopic Molecular Weight

412.370516166

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:28824 )
phytosterols (CHEBI:28824 )
stigmastane (C05442 )
Stigmasterols and C24-ethyl derivatives (C05442 )
Stigmastane and derivatives (C05442 )
Stigmasterols and C24-ethyl derivatives (LMST01040123 )

Ontology

Physiological effect

Health effect:

Health condition:

Sitosterolemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

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

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 84.40%; H 11.72%; O 3.88%	DFC
Melting Point	Mp 170°	DFC
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	[a]22D -57 (CHCl3)	DFC
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)	splash10-0a59-8920000000-c7d02c3957677fae28be	2015-03-01	View Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a4i-3941000000-4b20188a87c1dadeae49	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9720000000-02211a4df6ec5c313295	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-053r-7941000000-7983b2cb8a74cfda7530	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9731000000-168578ccead65322e450	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a4i-3941000000-4b20188a87c1dadeae49	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9720000000-02211a4df6ec5c313295	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-053r-7941000000-7983b2cb8a74cfda7530	Spectrum
GC-MS	Stigmasterol, non-derivatized, GC-MS Spectrum	splash10-0a59-9731000000-168578ccead65322e450	Spectrum
Predicted GC-MS	Stigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001j-1109000000-be897608aaeab74e5d13	Spectrum
Predicted GC-MS	Stigmasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0avl-2102900000-564b610342ad160ee822	Spectrum
Predicted GC-MS	Stigmasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Stigmasterol, 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, N/A (Annotated)	splash10-03di-0000900000-f7738a3fcdee344f82c9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-07cs-9400200000-959314bea26c5acd8301	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a59-7900000000-ce066e558ecbe29afea8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0a4i-3941000000-f854893a9352ff766734	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a59-9720000000-5a3d902c3cd2af078da3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-053r-7941000000-6c5c63e8c487f86b353b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a59-9731000000-32a70fa14fd448314caa	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2019500000-3495ed3a1955cc77528a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9128100000-3c3b91bb2d698a88f9db	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-8197000000-a80e8fcc32cd4a2dfefe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-322cae85ce921a9ef9e2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-d25be97b0cfa1b9bed79	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-2019000000-3b119d03e184f575cdc4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-2219400000-9acb072e76ff1b8f2e48	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-7259000000-a7f52c0e28b61ef2a3ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9320000000-8a54eac3182f86b7095b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-363450e12a0ea926276e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-fe3ab0b12c2d51198ed0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1001900000-43dce6fa5af31f5d7958	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	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

28824

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00937

CRC / DFC (Dictionary of Food Compounds) ID

HKT95-L:CBG86-I

EAFUS ID

Not Available

Dr. Duke ID

STIGMASTEROL

BIGG ID

Not Available

KNApSAcK ID

C00023774

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

Stigmasterol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00003674

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 hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti nociceptive	35470	An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.	DUKE
Anti ophidic		An antivenom agent used to treat venomous bites or stings, created by milking and diluting venom from relevant species, and injected to neutralize toxins, reducing inflammation and preventing systemic complications.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Artemicide		An herbicidal agent that targets and eliminates weeds of the Artemisia genus, with potential therapeutic applications in allergy management and anti-inflammatory uses, particularly for conditions exacerbated by Artemisia allergens.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Estrogenic		An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Ovulant		An agent that stimulates ovulation, the release of an ovum from an ovary, playing a key biological role in female fertility. Therapeutically, it is used to treat infertility and irregular menstrual cycles, with medical applications including induction of ovulation in women with polycystic ovary syndrome (PCOS) and other ovulatory disorders.	DUKE
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE