FComEx: Stigmasterol (PC000077)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:01 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000077

FoodDB Record

FDB001936

Chemical Information

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
(22E)-Stigmasta-5,22-dien-3-ol	biospider
(22E)-Stigmasta-5,22-dien-3beta-ol	biospider
(24S)-24-Ethylcholesta-5,22-dien-3beta-ol	biospider
(24S)-5,22-Stigmastadien-3β-ol	biospider
(24S)-5,22-stigmastadien-3b-ol	biospider
(24S)-5,22-Stigmastadien-3beta-ol	biospider
(24S)-Stigmast-5,22-dien-3beta-ol	biospider
(3b,22E)-Stigmasta-5,22-dien-3-ol	biospider
(3beta,22E)-Stigmasta-5,22-dien-3-ol	biospider
β-Stigmasterol	biospider
b-Stigmasterol	biospider
beta-Stigmasterol	biospider
D5-Stigmasterol	biospider
Delta5-Stigmasterol	biospider
Delta5,22-Stigmastadien-3beta-ol	biospider
Serposterol	db_source
Stigmasta-5,22-dien-3-b-ol	biospider
Stigmasta-5,22-dien-3-beta-ol	biospider
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
Stigmasterin	biospider
Stigmasterol	db_source

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

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