Sucrose Stearate

• CAS: 25168-73-4
• Catalog Number: ACM25168734
• Category: Main Products
• Molecular Weight: 608.76
• Molecular Formula: C30H56O12
• Synonyms: .beta.-D-Fructofuranosyl-.alpha.-D-Glucopyranoside,monooctadecanoate;alpha-d-glucopyranoside,beta-d-fructofuranosyl,monooctadecanoate;SUCROSE MONOSTEARATE;Sucrose stearate ester;Sucrose monostearic acid ester;Ryoto sugar ester S 1670;S-1670;Saccharose stearate
• IUPAC Name: [(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyloctadecanoate
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC1(C(C(C(O1)CO)O)O)OC2C(C(C(C(O2)CO)O)O)O
• InChI Key: SZYSLWCAWVWFLT-UTGHZIEOSA-N
• Boiling Point: 697.1ºC at 760mmHg
• Flash Point: 375.4°C
• Solubility: water, 0.02569 mg/L @ 25 °C (est)
• Appearance: COA
• Application: Sucrose stearate is a versatile ingredient that serves as a low-foam nonionic detergent and surfactant. It is commonly used as an emollient and emulsifying agent in makeup preparations, enabling the formulation of clear gel microemulsion systems with minimal impact on the skin and eyes. Additionally, sucrose stearate has been found to enhance the oral delivery of alendronate by improving intestinal absorption and displays antibacterial properties against various strains such as Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhimurium.
• Assay: 0.99
• EC Number: 246-705-9
• Exact Mass: 608.37700
• MDL Number: MFCD00152822
• Packaging: 1 kg
• Refractive Index: 1.546

Case Study

Flow Behavior Study of Sucrose Stearate/Water Systems

Calahorro, C., et al. Journal of the American Oil Chemists Society 69 (1992): 660-666.

Rheological studies were performed on aqueous systems containing nonionic surfactants derived from sugars. The composition range studied ranged from the micellar region to the appearance of fully developed liquid crystals. The study was performed at 50°C. The aim of this work was to investigate the rheological behavior of aqueous systems containing widely used sucrose esters under steady shear in a concentration range from the micellar region to the appearance of liquid crystals. The range of the linear viscoelastic domain was also investigated by strain sweep tests. Systems with up to 2 wt% sucrose stearate showed a significant decrease in the steady-state apparent viscosity with shear rate. At higher sucrose stearate concentrations, the flow curves presented two well-defined regions that depended on the shear rate, so that the apparent viscosity proposed the existence of three composition ranges. With increasing surfactant concentration, the micellar structure gradually strengthened up to a concentration of 10 wt% sucrose stearate. Between 15 and 35 wt% sucrose stearate, the results obtained were consistent with the appearance of lamellar liquid crystal dispersions in isotropic micellar solutions. The liquid crystal content in the dispersion increases steadily with increasing surfactant concentration until fully developed lamellar liquid crystals are reached at 40 wt% sucrose stearate.
Aqueous systems up to 45 wt% sucrose stearate (SE) were prepared to find fully developed liquid crystal structures within this composition range and to determine schematic phase diagrams between 5 and 60°C. The shear rate was varied between 0.1 s -I and 300 s -I. Strain sweep tests were performed using a sensor system {Re/Ri = 1.078). Results obtained for systems containing 1, 2, 3, 4, 11, 14 and 1 5 wt% SE at 50°C are presented. The tests were performed at a fixed frequency of 1 Hz and displacement angles ranging from 0.3° to 10°. All samples had the same recent history. Therefore, the sealed flasks containing the in situ prepared systems were brought to the desired test temperature by introducing them into a thermostatic circulator, used to keep the samples at 50 °C while the rheological measurements were performed. Before any measurements, all samples were placed in the sensor system for 10 min to achieve a certain stress relaxation.

Sucrose Stearate Emulsions for Dermal Drug Delivery Systems

Klang, Victoria, et al. Pharmaceutics 3.2 (2011): 275-306.

Mild nonionic sucrose ester surfactants can be used to produce lipid drug delivery systems for dermal applications. Moreover, moderately lipophilic sucrose esters, such as sucrose stearate S-970, have unique rheological behavior and can be used to produce highly viscous semisolid formulations without any additional additives. Interestingly, viscous macroemulsions and fluid nanoemulsions with the same chemical composition can be developed by only slightly changing the production process. Optical microscopy and cryo-transmission electron microscopy (TEM) revealed that the sucrose esters formed a striking hydrophilic network at a concentration of only 5% w/w in the macroemulsion system. Small amounts of finer structured aggregates composed of excess surfactant were similarly detected in the nanoemulsion.
The emulsification potential of different concentrations of 1 to 5% w/w sucrose stearate S-970 in O/W emulsions was tested. An increase in viscosity with increasing preparation method was noted, especially for 5% w/w sucrose stearate. When the surfactant concentration was higher than 5% w/w, highly viscous milky emulsions were obtained regardless of the preparation method, i.e., the emulsion microstructure was too viscous to pass through the high-pressure homogenizer even with heating. Therefore, the amount of sucrose stearate in the final formulation was 5% w/w. The composition of the resulting viscous macroemulsions and the corresponding fluid nanoemulsions was identical. The preparation of the separate aqueous and oil phases was identical in both cases. The aqueous phase consisting of freshly distilled water and potassium sorbate and the oil phase consisting of the cosmetic oil PCL-liquid were stirred at 50 °C, respectively. Blank and drug-loaded formulations were prepared. The lipophilic model drugs flufenamic acid, diclofenac, and curcumin were dissolved in the oil phase at a concentration of 0.5% (w/w), respectively. In the case of the crude emulsion, sucrose stearate S-970 was dissolved in the oil phase. The aqueous phase was slowly mixed and further stirred for 10 min, whereupon a highly viscous crude emulsion was obtained.

Sucrose Stearate Enhances Stability and Skin Permeability in Nanoemulsions

Klang, Victoria, et al. International Journal of Pharmaceutics 393.1-2 (2010): 153-161.

Lecithin-based nanoemulsions are colloidal drug delivery systems with fundamental advantages in topical treatments; however, their physicochemical long-term stability is generally rather poor without the use of additional synthetic surfactants. In a novel approach, negatively and positively charged formulations were developed without the use of conventional synthetic surfactants. Natural substances such as sucrose stearate and different cyclodextrins were additionally used as stabilizers. The optimized formulations were tested for their potential as drug delivery systems for progesterone. Furthermore, key formulation parameters such as particle size and zeta potential were monitored for more than one year. In this context, the effects of the natural excipients sucrose stearate and cyclodextrins on in vitro skin permeation were investigated; the effect of the positive particle surface charge caused by the incorporation of cationic phytosphingosine was also evaluated. The results showed that cyclodextrins in particular appear to induce fundamental changes in the microstructure of the formulations, as confirmed by cryo-TEM, leading to a significant increase in the skin permeability of progesterone compared to the control.
The aqueous and oil phases were first prepared separately. The aqueous phase, consisting of freshly distilled water and potassium sorbate, was stirred at 50 °C. In the respective formulations, sucrose esters such as sucrose stearate and CD or were incorporated into the aqueous phase. The oil phase consisted of PCL-liquid, Lipoid E-80, propylene glycol and tocopherol; phytosphingosine and progesterone were dissolved in the oil phase as well as in the respective formulations. The two phases were mixed and pre-homogenized at 2500 rpm for 4 min. Then, the mixture was stirred and heated to 50 °C and further homogenized with a high-pressure homogenizer at 750 bar for 16 homogenization cycles. The polydispersity index (PDI) values obtained represent the particle size distribution within the formulation. PDI values below 0.2 indicate a narrow size distribution; this indicates good long-term stability due to the reduction of degradation processes such as Ostwald ripening. The parameters of interest were measured immediately after the preparation of the formulations; the obtained nanoemulsions were stored at 4 °C and measured every two weeks for more than 12 months. Thus, information on the long-term stability of the formulation was obtained.

Effect of sucrose stearate as dispersant on microspheres

Horoz, B. Bahar, et al. AAPS PharmSciTech 7 (2006): E111-E117.

The effects of different concentrations of polymer and sucrose stearate and aluminum tristearate as dispersants on the properties and performance of microspheres were investigated. The yield of microspheres exceeded 78%, and the encapsulation efficiency was about 73%. The particle size of microspheres prepared by aluminum tristearate was between 76 and 448 μm, and the particle size of sucrose stearic acid microspheres was between 521 and 2000 μm. The morphology and physicochemical properties of the microspheres were studied by scanning electron microscopy and differential scanning calorimetry (DSC). DSC analysis showed that verapamil hydrochloride formed a solid solution with acrylic polymers. In vitro release studies were performed using a flow cell method. Microspheres containing aluminum tristearate released about 80% of the drug in 480 minutes, while microspheres containing sucrose stearic acid released the same amount of drug in only 60 minutes. The chemical structure and concentration of the dispersant significantly affected the physical properties of the microspheres and their drug release characteristics.
Verapamil hydrochloride and Eudragit RS 100 were dissolved in an acetone-methanol mixture. Dispersants such as sucrose stearate were added, and the mixture was stirred at 500 rpm in a water bath on a magnetic stirrer at 10 °C. The mixture was then quickly poured into liquid paraffin precooled to 10 °C while stirring at 400 rpm. The resulting emulsion was mixed at 35 °C for 4 h, and the organic solvent acetone-methanol was completely removed by evaporation. The solidified microspheres were filtered, washed 6 times with 50 mL of n-hexane in equal parts, dried under vacuum at room temperature overnight, and stored in a desiccator. Microspheres containing approximately 10 mg of verapamil hydrochloride were weighed and dissolved in methanol. The drug concentration was determined by UV spectrophotometry at 279 nm (n = 5).

Custom Q&A

What is the PubChem CID of Sucrose Stearate?

The PubChem CID of Sucrose Stearate is 9898327.

What is the molecular formula of Sucrose Stearate?

The molecular formula of Sucrose Stearate is C30H56O12.

What are the synonyms of Sucrose Stearate?

The synonyms of Sucrose Stearate include Sucrose, 1-stearate, 136152-91-5, and UNII-58RP7JU52K.

What is the molecular weight of Sucrose Stearate?

The molecular weight of Sucrose Stearate is 608.8 g/mol.

What is the IUPAC name of Sucrose Stearate?

The IUPAC name of Sucrose Stearate is [(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate.

What is the InChI of Sucrose Stearate?

The InChI of Sucrose Stearate is InChI=1S/C30H56O12/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(33)39-20-30(28(38)25(35)22(19-32)41-30)42-29-27(37)26(36)24(34)21(18-31)40-29/h21-22,24-29,31-32,34-38H,2-20H2,1H3/t21-,22-,24-,25-,26+,27-,28+,29-,30+/m1/s1.

What is the InChIKey of Sucrose Stearate?

The InChIKey of Sucrose Stearate is SZYSLWCAWVWFLT-UTGHZIEOSA-N.

What are the computed properties of Sucrose Stearate?

The computed properties of Sucrose Stearate include molecular weight (608.8 g/mol), XLogP3 (4.7), hydrogen bond donor count (7), hydrogen bond acceptor count (12), rotatable bond count (23), exact mass (608.37717722 g/mol), monoisotopic mass (608.37717722 g/mol), topological polar surface area (196?2), heavy atom count (42), formal charge (0), complexity (726), isotope atom count (0), defined atom stereocenter count (9), and undefined atom stereocenter count (0).

What is the CAS number of Sucrose Stearate?

The CAS number of Sucrose Stearate is 136152-91-5.

What is the EC number of Sucrose Stearate?

The EC number of Sucrose Stearate is 246-705-9.