Sitostanol

HCID 241572

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Basic information

CAS: 19466-47-8
Standard SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChIKey: LGJMUZUPVCAVPU-HRJGVYIJSA-N
Molecular formula: C29H52O
Average molar mass: 416.7 g/mol
Monoisotopic mass: 416.40181628

Overview

Stigmastanol is a 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. It has a role as an anticholesteremic drug and a plant metabolite. It is a member of phytosterols and a 3-hydroxy steroid. It derives from a hydride of a 5alpha-stigmastane.

Names & identifiers

Preferred name: Sitostanol
IUPAC: (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
English name: Stigmastanol
Molecular formula: C29H52O
Molecular weight: 416.72

Names & synonyms

STIGMASTANOLsitostanol83-45-4SpinastanolDihydrositosterin5alpha-Stigmastan-3beta-ol24alpha-Ethylcholestanol5,6-Dihydro-beta-sitosterolDihydro-beta-sitosterolStigmastan-3-ol, (3beta,5alpha)-C2NJ9WO6O7Dihydrositosterol

Show more names

FUCOSTANOLStigmastan-3β-olSTIGMASTAN-3BETA-OLSIGMASTANOLB-SITOSTANOLβ-sistostanolStigumastanolBETA-SITOSTANOL

NSC-49081CHEBI:89400(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol(3S,5S,8R,9S,10S,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-olRefChem:50712DTXSID50860237(3 beta,5 alpha)-stigmastan-3-ol24 alpha-ethyl-5alpha-choestan-3beta-ol

Database identifiers

CAS: 19466-47-8、83-45-4
PubChem CID: 241572
DTXSID: DTXSID201016169
ChEMBL: CHEMBL252364
ChEBI: CHEBI:89400
UNII: C2NJ9WO6O7
EC Number: 201-479-0
Nikkaji: J4.631K

Properties

Computed structural properties

XLogP: 10.2
Topological polar surface area: 20.2 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 6
Heavy atoms: 30
Formal charge: 0
Complexity: 583

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Stigmasterols and C24-ethyl derivatives [ST0104]

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 137 °C · 137 °C
Boiling point: 471.9 · 471.9±13.0 °C(Predicted)
Density: 0.948 · 0.948±0.06 g/cm3(Predicted)
storage temp.: Refrigerator
solubility: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
pka: 15.14 · 15.14±0.70(Predicted)
color: White to Off-White
Merck: 8814 · 8814
InChIKey: LGJMUZUPVCAVPU-FNTHTIGCNA-N
SMILES: [C@@]12([H])CC[C@@]3([H])C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])[C@H](C)CC[C@@H](CC)C(C)C |&1:0,4,7,11,13,17,19,22,24,28,r|
CAS DataBase Reference: 19466 · 19466-47-8
FDA UNII: 2 NJ9WO6O7 · C2NJ9WO6O7
EPA Substance Registry System: -3 · Stigmastan-3.beta.-ol (19466-47-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 21 · NA.21
Hazard statements: 413 · H413
Precautionary statements: 273 · P273
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24-26-36
WGK Germany: -
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 · Aquatic Chronic 4

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: Stigmastan-3-ol, (3.beta.,5.alpha.)-

Stigmastan-3-ol, (3.beta.,5.alpha.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

wgk: -
risk_code: 36/37/38
hazard_code: Xi
safety_code: 24-26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H413
Hazard Classifications: Aquatic Chronic 4
Precautionary statements: P273

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances used to lower plasma CHOLESTEROL levels.

Applications

UsesStigmastanol is a plant lipid molecule that resembles cholesterol.

Suppliers32 total

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]

上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]

安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]

Related reactions

1 records

New reaction record

HRID 366281As reactantuspto-grants-2000_10

Compound notes

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