Пальмитат ситостерина

Description

Sitosterol palmitate is an ester of the phytosterol β-sitosterol and palmitic acid, that is, a 16:0 ester of sitosterol. Class: steroids, sterol esters. Obtained by esterification of sitosterol with palmitic acid in the presence of an esterifying agent; In nature, the substance is found in plant lipid fractions. The lipophilicity of the product is extremely high, so it is introduced into the fatty phase of the composition, and not into the aqueous phase.

Identification

• CAS No: 2308-85-2
• Chemical formula: C45H80O2
• English name: Sitosterol palmitate
• UNII:LEB596GYDL
• Class: steroids, phytosterol esters
• Synonyms: β-sitosterol palmitate; sitosteryl palmitate; β-sitosteryl palmitate; β-sitosterol hexadecanoate; stigmast-5-en-3β-ol, palmitate; stigmast-5-en-3-ol, 3-hexadecanoate, (3β)-; palmitic acid, β-sitosteryl ester; β-rosasterol palmitate

Basic Attributes

• Molecular weight: 653.133
• Exact weight: 653.12
• PSA specifications: 26.3
• XLogP3: 19.02
• Density: 1.0 ± 0.1 g/cm³
• Melting point: 88–88.5 °C
• Boiling point: 669.0 ± 34.0 °C at 760 mm Hg. Art.
• Flash point: 358.8 ± 13.2 °C
• Refractive index: 1.505

An XLogP3 value of about 19 and a small polar surface area of ​​26.3 Ų describe an essentially non-polar substance: the free hydroxyl group of the sterol is capped by an ester bond, and a sixteen-carbon chain is added to the molecule.

Structure

β-Sitosterol is a plant sterol of the stigmastane series with 29 carbon atoms, differing from cholesterol by the ethyl group at C-24. In palmitate, the hydroxyl at position 3β is esterified with a palmitic (hexadecanoic) acid residue. When embedded in a lipid bilayer, the sterol core is oriented in a ring system along the hydrophobic acyl chains, which changes the fluidity of the membrane.

Scope of application

• lipidology and pharmacology: compound is being studied in relation to hyperlipidemia; described inhibition of cholesterol esterase, an enzyme that breaks down cholesteryl esters into free cholesterol and fatty acids
• food direction: phytosterol esters are used as safe food components
• cosmetic formulations: fat phase ingredient
• analytics: standard sample for the determination of sterol esters in vegetable oils and extracts by GC and HPLC methods

Working with the product

The substance is dissolved in non-polar and low-polar organic solvents; it does not pass into water. The mixture is introduced into the formulation through the fat phase when heated above the melting point of 88–88.5 °C, followed by homogenization.

Storage

Tightly closed container, cool, dry place, protected from light and atmospheric oxygen: long-chain esters are prone to oxidation upon prolonged contact with air. When working with powder, wear gloves and safety glasses.