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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H50O
Molecular Weight 414.7067
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of β-sitosterol

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

InChI

InChIKey=KZJWDPNRJALLNS-VJSFXXLFSA-N
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

HIDE SMILES / InChI
Molecular Formula C29H50O
Molecular Weight 414.7067
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Beta-sitosterol is one of the main dietary phytosterols found in plants which have a similar skeleton as cholesterol. In human clinical trials, beta-sitosterol has been shown to have cholesterol-lowering effects and to relieve symptoms of benign prostatic hyperplasia. There has been a large amount of basic research conducted for potential applications of beta-sitosterol in a diverse range of conditions including cervical cancer, breast cancer, cystic fibrosis, and others. Beta-sitosterol is available over the counter as a natural health supplement and is marketed for a wide range of applications including headaches, tuberculosis, allergies, cancers, fibromyalgia, lupus, asthma, hair loss and many others.

Originator

Approval Year

1956
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Caspase-3
21
Target ID: P42574
Gene ID: 836.0
Gene Symbol: CASP3
Target Organism: Homo sapiens (Human)
Activator
1430
Protein kinase C alpha type
5
Target ID: P17252
Gene ID: 5578.0
Gene Symbol: PRKCA
Target Organism: Homo sapiens (Human)
Interacts
323
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Dietary supplements for benign prostatic hyperplasia: an overview of systematic reviews.
2012 Nov
Patents

Patents

CN101606525
2
EP0057075B
2
US3332969
2
US4153622
2
US4279827
2
US5118671
2
US5747464
2
WO1995000158
2

Sample Use Guides

In Vivo Use Guide
Over 6 to 8 weeks beta-sitosterol supplementation of 12 g/day resulted in an average of 11% decrease in serum cholesterol and a 12% decrease in biliary cholesterol saturation.
Route of Administration: Oral
In Vitro Use Guide
Human cervical cancer cell lines, Caski and HeLa, were cultured in RPMI-1640 and supplemented with 10% foetal bovine serum and incubated at 37 deg-c in an atmosphere with 5% CO2. Cells were treated with 20 umol/L of beta-sitosterol for 48 hours and examined for changes by light microscopy, electron microscopy, and transmission electron microscopy. Changes in mRNA and protein expression were quantified using Real-Time qPCR and western blots. The treatment with beta-sitosterol reduced expression of PCNA, increased p53 mRNA, decreased the amount of HPV E6 transcripts. Cells treated with beta-sitosterol also exhibited loss of cell surface microvilli and increased electron density in the cell membrane.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:47 UTC 2023
Edited
by admin
on Fri Dec 15 15:05:47 UTC 2023
Record UNII
S347WMO6M4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
β-sitosterol
MI  
Common Name English
.ALPHA.-PHYTOSTEROL
Common Name English
(3.BETA.)-STIGMAST-5-EN-3-OL
Systematic Name English
BETA-SISTOSTEROL
Common Name English
BETAPROST
Common Name English
PROSTASAL
Brand Name English
AZUPROSTAT
Common Name English
BETA SITOSTEROL
VANDF  
Common Name English
BETA-SITOSTEROL (CONSTITUENT OF STINGING NETTLE) [DSC]
Common Name English
SITOSTEROL, .BETA.
Common Name English
.BETA.-SITOSTEROL [MI]
Common Name English
SITOSTERIN
Common Name English
HARZOL
Brand Name English
BETA-SITOSTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
SITOSTEROL, BETA
Common Name English
22,23-DIHYDROSTIGMASTEROL
Common Name English
CUPREOL
Common Name English
RHAMNOL
Common Name English
NSC-18173
Code English
SKF 14463
Code English
QUEBRACHOL
Common Name English
BETA-SITOSTEROL [USP-RS]
Common Name English
BETA-SITOSTEROL [INCI]
Common Name English
SITOSTEROL [MART.]
Common Name English
.BETA.-SITOSTEROL (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]
Common Name English
Beta-sitosterol [WHO-DD]
Common Name English
24.BETA.-ETHYL-.DELTA.(SUP 5)-CHOLESTEN-3.BETA.-OL
Common Name English
BETA SITOSTEROL [VANDF]
Common Name English
NSC-8096
Code English
.DELTA.(SUP 5)-STIGMASTEN-3.BETA.-OL
Common Name English
CINCHOL
Common Name English
SITOSTEROL, BETA-
Common Name English
.BETA.-SITOSTEROL (CONSTITUENT OF PYGEUM) [DSC]
Common Name English
BETA-SITOSTEROL
INCI   USP-RS  
INCI  
Official Name English
.ALPHA.-DIHYDROFUCOSTEROL
Common Name English
NSC-49083
Code English
Classification Tree Code System Code
DSLD 1062 (Number of products:256)
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
NCI_THESAURUS C68437
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
LOINC 75741-9
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
DSLD 2256 (Number of products:9)
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
Code System Code Type Description
CAS
83-46-5
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
NSC
18173
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
WIKIPEDIA
BETA-SITOSTEROL
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
PUBCHEM
222284
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
CAS
15764-35-9
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
SUPERSEDED
CAS
5779-62-4
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
182512-23-8
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
SUPERSEDED
SMS_ID
100000090258
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
DRUG BANK
DB14038
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
RXCUI
47070
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY RxNorm
NSC
8096
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
DAILYMED
S347WMO6M4
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
EVMPD
SUB27060
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
CHEBI
27693
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
MERCK INDEX
m9964
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY Merck Index
CAS
8003-23-4
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
SUPERSEDED
ECHA (EC/EINECS)
201-480-6
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
NCI_THESAURUS
C63662
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
FDA UNII
S347WMO6M4
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
NSC
49083
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
CAS
76772-70-8
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID5022481
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1612947
Created by admin on Fri Dec 15 15:05:48 UTC 2023 , Edited by admin on Fri Dec 15 15:05:48 UTC 2023
PRIMARY
Related Record Type Details
VIBURNUM OPULUS BARK
PARENT -> CONSTITUENT ALWAYS PRESENT
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
EUPATORIUM PERFOLIATUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
COMFREY ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
COMFREY LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
PAEONIA X SUFFRUTICOSA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
DIOSCOREA POLYSTACHYA TUBER
PARENT -> CONSTITUENT ALWAYS PRESENT
IRIS VERSICOLOR ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
PLANTAGO OVATA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Related Record Type Details
Structure of β-sitosterol
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