(-)-beta-Sitosterol

HCID 222284
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
5779-62-4
Standard SMILES
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChIKey
KZJWDPNRJALLNS-VJSFXXLFSA-N
Molecular formula
C29H50O
Average molar mass
414.7 g/mol
Monoisotopic mass
414.38616621

Names & identifiers

Preferred name
(-)-beta-Sitosterol
IUPAC
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
English name
beta-Sitosterol
Molecular formula
C29H50O
Molecular weight
414.72

Names & synonyms

BETA-SITOSTEROL83-46-5SitosterolAzuprostatCincholQuebracholRhamnol22,23-Dihydrostigmasterolbeta-SitosterinTriastonal(-)-beta-SitosterolNimbosterol
Show more names
β-SitosterolPHYTOSTEROLSterolStigmast-5-en-3beta-olSITO
alpha-DihydrofucosterolProstasal24alpha-EthylcholesterolB-Sitosterol(24R)-Ethylcholest-5-en-3beta-ol(3beta)-Stigmast-5-en-3-ol(24R)-Stigmast-5-en-3beta-ol24-alpha-Ethylcholesterol

Database identifiers

CAS
5779-62-4、83-46-5
PubChem CID
222284
DTXSID
DTXSID5022481
ChEMBL
CHEMBL221542
ChEBI
CHEBI:27693
UNII
S347WMO6M4
EC Number
201-480-6
Nikkaji
J4.633G

Properties

Computed structural properties

XLogP
9.3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
30

Experimental & physicochemical properties

Solubility10 mg/mL
Melting Point140 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
136 · 136-140 °C(lit.)
Boiling point
473.52 °C · 473.52°C (rough estimate)
alpha
-28 · -28 º (c=2, CHCl3)
Density
0.954 · 0.9540 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99% (99 of 100) of all reports.

Not Classified；Reported as not meeting GHS hazard criteria by 99 of 100 companies (only 1% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 100 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 99 of 100 reports by companies.；There is 1 notification provided by 1 of 100 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Chemical: Stigmast-5-en-3-ol, (3.beta.)-

Stigmast-5-en-3-ol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesNot Classified

Toxicology

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

beta-Sitosterol

Waste-water effluent contaminant

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Regulatory information

Regulatory Information · 2 items

Chemical: Stigmast-5-en-3-ol, (3.beta.)-

Stigmast-5-en-3-ol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
10
wgk
3
rtecs
WJ2600000
ridadr
UN 1888 6.1/PG 3
hs_code
29061990
risk_code
22-38-40-48/20/22-36/37/38-67-36/38-20-63

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Tissue LocationsFibroblasts；Intestine；Kidney；Liver；Prostate；Testis
Cellular LocationsExtracellular；Membrane

Uses & manufacturing

Uses · 2 items

CIR ingredient: Beta-Sitosterol

Use (kg; approx.) in Germany (2009): >75；Consumption (g per capita; approx.) in Germany (2009): 0.000916；Calculated removal (%): 97.7

Use ClassificationCosmetics -> Emulsion stabilizing; Stabilizing; Skin conditioning
Applications · 4 items

Description24α-ethyl Cholesterol is a naturally occurring plant sterol with antioxidant, anticancer, anti-inflammatory, angiogenic, chemopreventive, and immunomodulatory activities. It inhibits the absorption of dietary and endogenously-produced cholesterol from the small intestine, reducing blood cholesterol concentrations. Because of its nutraceutical benefits, 24α-ethyl cholesterol has been used as a food additive intended to lower LDL cholesterol. 24α-ethyl Cholesterol (0.1 - 100 μM) can dose-dependently induce adipogenesis and lipolysis in rat primary preadipocytes as well as stimulate glucose uptake in differentiated adipocytes.

Usesantiinflammatory, immunomodulator

UsesA common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.This compound is a contaminant of emerging concern (CECs)

General DescriptionSitosterol, also called as β-sitosterol, is synthesized through the mevalonate and deoxy xylulose pathways. Synthetically, it is synthesized from stigmasterol by Δ22–23 alkene group hydrogenation. Structurally sitosterol differ from cholesterol with ethyl (sitosterol) group in C24 position of side chain(65). Sitosterol is a lipid component of membranes. It corresponds to a molecular mass of 414.71 g/mol).

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Additional notes · 3 items

DefinitionA steroid with long aliphatic side chains (8–10 carbons) and at least one hydroxyl group. They are lipidsoluble and often occur in membranes. Examples are cholesterol and ergosterol.

Definitionsterol: Any of a group of steroidbasedalcohols having a hydrocarbonside-chain of 8–10 carbon atoms.Sterols exist either as free sterols oras esters of fatty acids. Animal sterols(zoosterols) include cholesterol andlanosterol. The major plant sterol(phytosterol) is beta-sitosterol, whilefungal sterols (mycosterols) includeergosterol.

DefinitionChEBI: A phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.

Related reactions

4 records
New reaction record

Compound notes

Loading…