Stigmastanol

• CAS: 83-45-4
• Catalog Number: ACM83454-4
• Category: Main Products
• Molecular Weight: 416.72
• Molecular Formula: C29H52O
• Synonyms: 24-ALPHA-ETHYLCHOLESTANOL
• Appearance: White Solid

Case Study

Stigmastanol as a Reference Cholesterol Absorption Inhibitor Affecting Vitamin D3 and K1 Absorption

Ibrahim, Fady, et al. European Journal of Pharmaceutical Sciences 49.2 (2013): 125-132.

Stigmastanol, a phytosterol structurally similar to cholesterol, serves as a positive control inhibitor of intestinal cholesterol absorption. It competes with lipophilic compounds for micellar solubilization, thereby reducing the systemic exposure of co-administered lipid-soluble vitamins, particularly vitamin D3 which shares structural homology with cholesterol.
Experimental Protocol: Male Sprague-Dawley rats received a single oral gavage of vitamin D3 (1 mg/kg) and vitamin K1 (5 mg/kg) in peanut oil together with stigmastanol suspension (50 mg/kg in 2% sodium carboxymethyl cellulose with 1% Tween-80). A control group received the vitamins without stigmastanol. Plasma concentrations were measured over 48 h by HPLC. An in vitro lipolysis model simulating fed-state intestinal conditions was also used to assess vitamin distribution among oil, aqueous and sediment phases.
Performance Evaluation: Stigmastanol reduced the Cmax of vitamin D3 from 1419.5 to 912.5 ng/mL and its bioavailability (F) from 0.44 to 0.27 (p < 0.05). For vitamin K1, Cmax decreased from 1778.4 to 1147.1 ng/mL and F from 0.24 to 0.14, though the change was not statistically significant. In the lipolysis model, stigmastanol shifted vitamin D3 distribution from the aqueous phase toward the sediment, while vitamin K1 distribution remained unchanged.
Stigmastanol effectively reduces the oral bioavailability of vitamin D3 by interfering with its intestinal micellar solubilisation, an effect attributed to structural similarity between vitamin D3 and cholesterol. This makes stigmastanol a suitable reference standard for evaluating cholesterol-absorption inhibitors.

Stigmastanol as a Lipophilic Phytosterol Affecting Cholesterol Intestinal Processing

Zhao, Jinying, et al. International journal of pharmaceutics 436.1-2 (2012): 707-710.

Stigmastanol, a lipophilic phytostanol, reduces cholesterol absorption by redistributing cholesterol from the absorbable aqueous phase to the oil and sediment phases during lipid digestion, but its efficacy is highly dependent on formulation due to its poor water solubility.
Experimental Protocol: An in vitro lipolysis model simulating fasted and fed intestinal conditions was used. Stigmastanol was tested in two forms: (i) powder alone (262.5 mg) and (ii) a suspension formulation (262.5 mg wetted with Tween-80 in 2% sodium carboxymethyl cellulose). The distribution of cholesterol among oil, aqueous and sediment phases after ultracentrifugation was measured and compared to a water control.
Performance Evaluation: Stigmastanol powder had no significant effect on cholesterol distribution in either fasted or fed state. In contrast, the suspension formulation significantly reduced cholesterol in the aqueous phase (from ~70% to ~55% under fed conditions) and redistributed it into the oil and sediment phases. This redistribution suggests delayed absorption (oil phase) and increased faecal excretion (sediment phase). The magnitude of change was modest compared to the water-soluble analogue DAPP, which shifted cholesterol almost exclusively to the sediment phase.
Stigmastanol can interfere with intestinal cholesterol processing, but its poor solubility necessitates a suitable formulation to achieve efficacy.

Custom Q&A

What is the PubChem CID for stigmastanol?

The PubChem CID for stigmastanol is 241572.

What is the molecular formula of stigmastanol?

The molecular formula of stigmastanol is C29H52O.

What is the molecular weight of stigmastanol?

The molecular weight of stigmastanol is 416.7 g/mol.

What are the synonyms for stigmastanol?

The synonyms for stigmastanol include sitostanol, Fucostanol, and Spinastanol.

What is the IUPAC name of stigmastanol?

The IUPAC name of stigmastanol is (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.

What is the InChI of stigmastanol?

The InChI of stigmastanol is InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22+,23+,24-,25-,26+,27+,28+,29-/m1/s1.

What is the canonical SMILES of stigmastanol?

The canonical SMILES of stigmastanol is CCC(CCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)C(C)C.

What is the CAS number for stigmastanol?

The CAS number for stigmastanol is 83-45-4.

What is the European Community (EC) number for stigmastanol?

The European Community (EC) number for stigmastanol is 201-479-0.

What is the Wikipedia page for stigmastanol?

The Wikipedia page for stigmastanol can be found at Stigmastanol.