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Home> Encyclopedia >Cardiovascular Agents>Pharmaceutical Intermediates>Herbal Extract
beta-Sitosterol structure
beta-Sitosterol structure

beta-Sitosterol

Iupac Name:(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
CAS No.: 83-46-5
Molecular Weight:414.71
Modify Date.: 2022-11-29 04:23
Introduction: A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma. View more+
1. Names and Identifiers
1.1 Name
beta-Sitosterol
1.2 Synonyms

(24R)-Stigmast-5-en-3b-ol (3)-BETA-SITOSTEROL(2) (3b)-Stigmast-5-en-3-ol (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-éthyl-6-méthyl-2-heptanyl]-10,13-diméthyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-3-ol (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-Ethyl-6-methyl-2-heptanyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (3Β)-Stigmast-5-en-3-ol (3Β,20R,24R)-Stigmast-5-en-3-ol 22,23-DIHYDROSTIGMASTEROL 22,23-DIHYDROSTIMASTEROL 22:23-Dihydrostigmasterol 24-ALPHA-ETHYLCHOLESTEROL 24BETA-ETHYLCHOLESTEROL 24b-Ethyl-D5-cholesten-3b-ol 5-CHOLESTEN-24-BETA-ETHYL-3-BETA-OL 5-STIGMASTEN-3BETA-OL a-Dihydrofucosterol a-Phytosterol b-Sitosterin B-SITOSTEROL D5-Stigmasten-3b-ol EINECS 201-480-6 L E5 B666 LUTJ A1 E1 FY1&2Y2&Y1&1 OQ &&Stereoisomer MFCD00003631 Prostasal Sitosterin Sitosterol Sitosterol Β Stigmast-5-en-3b-ol Stigmast-5-en-3-ol, (3Β)- Stigmast-5-en-3-ol, (3Β,20R,24R)- α-Dihydrofucosterol α-Phytosterol Β-Sitosterol Δ5-Stigmasten-3b-ol

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1.3 CAS No.
83-46-5
1.4 CID
222284
1.5 EINECS(EC#)
271-413-3; 201-480-6
1.6 Molecular Formula
C29H50O (isomer)
1.7 Inchi
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
1.8 InChIkey
KZJWDPNRJALLNS-VJSFXXLFSA-N
1.9 Canonical Smiles
CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
1.10 Isomers Smiles
CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
2. Properties
2.1 Density
0.9540 (rough estimate)
2.1 Melting point
136-140 °C(lit.)
2.1 Boiling point
473.52°C (rough estimate)
2.1 Refractive index
1.5000 (estimate)
2.1 Flash Point
226.3°C
2.1 Precise Quality
428.40200
2.1 PSA
20.23000
2.1 logP
8.41490
2.1 Solubility
chloroform: 20?mg/mL, clear, colorless
2.2 Appearance
Solid
2.3 Chemical Properties
White powder
2.4 pKa
15.03±0.70(Predicted)
2.5 Water Solubility
H2O: INsoluble
2.6 StorageTemp
?20°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.
3.2 Usage
A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.
4. Safety and Handling
4.1 Symbol
GHS06, GHS08
4.1 Hazard Codes
Xn,Xi
4.1 Signal Word
Danger
4.1 Risk Statements
22-38-40-48/20/22-36/37/38-67-36/38-20-63
4.1 Safety Statements
22-24/25-36-26-36/37
4.1 Hazard Declaration
H302-H315-H319-H331-H336-H351-H361d-H372
4.1 RIDADR
UN 1888 6.1/PG 3
4.1 Caution Statement
P201-P261-P304 + P340 + P312-P305 + P351 + P338-P308 + P313-P403 + P233
4.1 WGK Germany
3
4.1 RTECS
WJ2600000
4.1 Specification

The Beta-sitosterol, with the?CAS registry number 83-46-5, is a kind of white powder with no odour. This chemical is insoluble in water while soluble in chloroform and carbon disulfide, with the product categories including Miscellaneous Natural Products; Biochemistry; Hydroxysteroids; Steroids; Natural Plant Extract. As to its usage, it is widely applied in many ways. It could be used as the Lipid-lowering drugs, and it could also be used as the acridine and health food.

The physical properties of this chemical are as below: (1)ACD/LogP: 10.73; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 7; (6)Polar Surface Area: 9.23; (7)Index of Refraction: 1.521; (8)Molar Refractivity: 129.21 cm3; (9)Molar Volume: 424.3 cm3; (10)Polarizability: 51.22 ×10-24 cm3; (11)Surface Tension: 37.6 dyne/cm; (12)Density: 0.97 g/cm3; (13)Flash Point: 220.4 °C; (14)Enthalpy of Vaporization: 88.77 kJ/mol; (15)Boiling Point: 501.9 °C at 760 mmHg; (16)Vapour Pressure: 3.53E-12 mmHg at 25°C; (17)Exact Mass: 414.386166; (18)MonoIsotopic Mass: 414.386166; (19)Topological Polar Surface Area: 20.2; (20)Heavy Atom Count: 30; (21)Complexity: 634.

When you deal with this chemical, you should be careful. For one thing, it is irritant to eyes, respiratory system and skin, which may also cause inflammation to the skin or other mucous membranes. For another thing, it is harmful? which may cause damage to health, and it may have danger of serious damage to health by prolonged exposure through inhalation and if swallowed. Besides, it has the limited evidence of a carcinogenic effect. Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, then avoid contacting with skin and eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, remember not to breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
(2)Isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
(3)InChI: 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
(4)InChIKey: KZJWDPNRJALLNS-VJSFXXLFSA-N?

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4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WJ2600000
CHEMICAL NAME :
Stigmast-5-en-3-beta-ol
CAS REGISTRY NUMBER :
83-46-5
LAST UPDATED :
199706
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C29-H50-O
MOLECULAR WEIGHT :
414.79

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 46,461,1976
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Mesh
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)
9.1 Mesh Entry Terms
24-ethylcholest-5-en-3 beta-ol
9.2 Use Classification
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Stigmasterols and C24-ethyl derivatives [ST0104]|Cosmetics -> Emulsion stabilizing; Skin conditioning; Stabilizing
10. Computational chemical data
  • Molecular Weight: 414.71g/mol
  • Molecular Formula: C29H50O
  • Compound Is Canonicalized: True
  • XLogP3-AA: 9.3
  • Exact Mass: 414.386166214
  • Monoisotopic Mass: 414.386166214
  • Complexity: 634
  • Rotatable Bond Count: 6
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Topological Polar Surface Area: 20.2
  • Heavy Atom Count: 30
  • Defined Atom Stereocenter Count: 9
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB4IAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGCAAAAAGgAACAAADxSggAICAAAAAgCAAiBCAAAAAAAgAAAACAAAAAgAEAIAAQAAQAAEwAAIAAOAwPAPgAAAAAAAAADAAAQAACAAAQAACAAAAA==
11. Question & Answer
  • beta-Sitosterol is a natural plant molecule that is similar to cholesterol. It is mainly found in various plants, especially in sunflowers, nuts, legumes, and plant oils. In this article, we will expl..
  • The beta-Sitosterol can be considered as the nemesis of cholesterol. Consuming a moderate amount of beta-Sitosterol every day can bring great benefits to the body. However, even though beta-Sitosterol..
  • The characteristics of beta-Sitosterol are quite evident, with powerful control over reverse membrane permeability and a certain degree of hydrophobicity. It has a wide range of biological functions a..
  • beta-Sitosterol (β-sitosterol) is widely found in the fruits and seeds of various plants, as well as in various vegetables and fruits. It is a valuable medicinal raw material and intermediate. Natura..
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