U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H52O
Molecular Weight 416.7237
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STIGMASTANOL

SMILES

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

InChI

InChIKey=LGJMUZUPVCAVPU-HRJGVYIJSA-N
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/t20-,21-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H52O
Molecular Weight 416.7237
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Stigmastanol is a plant lipid molecule that resembles cholesterol in structure. It inhibits cholesterol absorption. Sitostanol powder (1 g) reduced cholesterol absorption by only 11.3 /- 7.4% (P = 0.2), confirming in vitro data showing poor solubility of sitostanol powder in artificial bile. In contrast, sitostanol in lecithin micelles reduced cholesterol absorption by 36.7 /- 4.2% (P = 0.003) at a dose of 700 mg and by 34.4 /- 5.8% (P = 0.01) at a dose of 300 mg. Stigmasterol, which is used for the synthesis of progesterone and vitamin D3 is a potential anti-inflammatory compound. Its action is mediated by the inhibition of several pro-inflammatory and matrix degradation mediators involved in osteoarthritis-induced cartilage degradation.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The conversion of cholest-5-en-3beta-ol into cholest-7-en-3beta-ol by the echinoderms Asterias rubens and Solaster papposus.
1975 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: The administration of a dairy product in the form of liquid yoghurt, marketed in Spain, that contains 2 g per container of plant stanol esters: sitostanol (Stigmastanol) and campestanol (AHA recommended dose - 1.5 to 3 g). The enriched product and the placebo will have the same characteristics (composition and outward appearance), but the placebo will not contain stanol esters. The dose will be one container a day, after the main meal, for 24 months. The participants may continue with their previously prescribed lipid-lowering treatment and new treatment needed for this disease or for other diseases. Composition per container: proteins 1.8 g, carbohydrates 9.8 g, fat (except stanol) 1.4 g, plant stanol 2 g, vitamin B6 0.6 mg, folic acid 60 mg. The control group will receive one unit a day of yoghurt not supplemented with stanol esters that has a similar appearance to the enriched yoghurt. https://clinicaltrials.gov/ct2/show/NCT01406106
From a total number of 137 male subjects with hypercholesterolemia, eight subjects with the lowest and eight subjects with the highest ratios of lathosterol to campesterol in serum were included in the study. They received 1 g sitostanol (Stigmastanol)-supplemented margarine b.i.d. for four weeks.
Route of Administration: Oral
Mouse bone marrow derived macrophages incubated with plant stanols produced less Tnf-a after exposure to sitostanol (Stigmastanol), both after 0.6 and 1.2 um concentrations as compared to cyclodextrin (carrier control).
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:01:17 UTC 2021
Edited
by admin
on Sat Jun 26 09:01:17 UTC 2021
Record UNII
C2NJ9WO6O7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STIGMASTANOL
MI   WHO-DD  
Systematic Name English
DIHYDRO-.BETA.-SITOSTEROL
Common Name English
.BETA.-SITOSTANOL
Common Name English
STIGMASTANOL [MI]
Common Name English
STIGMASTANOL (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
NSC-49081
Code English
(3.BETA.,5.ALPHA.)-STIGMASTAN-3-OL
Systematic Name English
24.ALPHA.-ETHYLCHOLESTANOL
Systematic Name English
SITOSTANOL
MART.  
Common Name English
SITOSTANOL [MART.]
Common Name English
FUCOSTANOL
Common Name English
STIGMASTANOL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68422
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
LOINC 74887-1
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
DSLD 2050 (Number of products:4)
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
DSLD 1905 (Number of products:6)
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
DSLD 4138 (Number of products:1)
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
Code System Code Type Description
PUBCHEM
241572
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
CAS
83-45-4
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
MERCK INDEX
M10213
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY Merck Index
EVMPD
SUB129669
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-479-0
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
WIKIPEDIA
Stigmastanol
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
FDA UNII
C2NJ9WO6O7
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
NCI_THESAURUS
C68323
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
MESH
C021255
Created by admin on Sat Jun 26 09:01:17 UTC 2021 , Edited by admin on Sat Jun 26 09:01:17 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Related Record Type Details
ACTIVE MOIETY