Stigmasterol
[CAS# 83-48-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Thiopyrimidine
• Name: Stigmasterol
• Synonyms: Stigmasta-5,22-dien-3beta-ol
• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.70
• CAS Registry Number: 83-48-7
• EC Number: 201-482-7
• SMILES: CC[C@H](/C=C/[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

Properties

• Solubility: Insoluble 7.277e-005 mg/L (25 °C water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.531, Calc.^*
• Melting point: 171.80 °C
• Boiling Point: 501.1±19.0 °C (760 mmHg), Calc.^*, 452.55 °C
• alpha: -50 ° (c=2, CHCl3)
• Flash Point: 219.4±13.7 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Stigmasterol, a plant sterol, was first isolated in the early 20th century from soybean oil. It was identified by scientists who were studying the components of plant oils and their potential health benefits. Named after the Calabar bean's scientific name, Physostigma venenosum, from which it was also derived, stigmasterol became a significant focus due to its structural similarity to cholesterol. The compound was found to be a crucial phytosterol.

Stigmasterol has a wide range of applications in different fields due to its beneficial properties. Stigmasterol is a key ingredient in dietary supplements aimed at lowering cholesterol levels. As a plant sterol, it competes with cholesterol for absorption in the digestive system, thereby reducing the overall levels of cholesterol in the blood.

In pharmaceuticals, stigmasterol is used as a precursor in the synthesis of steroid hormones, including progesterone and other corticosteroids. Its structure serves as a starting material for the production of these hormones, which are essential in various treatments, including hormone replacement therapy and anti-inflammatory drugs.

Stigmasterol is incorporated into cosmetics and skincare products for its anti-inflammatory and skin-soothing properties. It helps in reducing skin redness and irritation, making it a beneficial component in creams and lotions designed for sensitive skin. Additionally, its antioxidant properties help protect the skin from environmental damage and aging.

As a natural compound found in vegetables and nuts, stigmasterol is added to functional foods to enhance their nutritional profile. Foods fortified with plant sterols, including stigmasterol, can help consumers manage their cholesterol levels more effectively.

Stigmasterol is used in agriculture as a growth-promoting agent for plants. It has been shown to improve the growth and yield of crops by enhancing their stress resistance and overall vitality.

Researchers utilize stigmasterol in studies to understand its effects on human health, particularly its role in reducing cholesterol levels and its potential anti-cancer properties. Studies have indicated that stigmasterol may inhibit the growth of certain cancer cells.

References

2012. Dietary intake of plant sterols stably increases plant sterol levels in the murine brain. Journal of Lipid Research, 53(4).
DOI: 10.1194/jlr.m017244

2005. Bioconversion of phytosterols to androstanes by mycobacteria growing on sugar cane mud. Journal of Industrial Microbiology and Biotechnology, 32(3).
DOI: 10.1007/s10295-004-0196-8

1979. Utilization of various sterols by lecithin-cholesterol acyltransferase as acyl acceptors. Lipids, 14(5).
DOI: 10.1007/bf02533465