20905-61-7

Basic information

• Product Name: 24,25-dihydroxylanost-8-en-3-yl acetate
• CAS NO: 20905-61-7
• Molecular Formula: C₃₂H₅₄O₄
• Molecular Weight: 502.7688
• Mol File: 20905-61-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 575.3°C at 760 mmHg
• Flash Point: 172.1°C
• Density: 1.06g/cm³
• Vapor Pressure: 1.25E-15mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: 24,25-dihydroxylanost-8-en-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 24,25-dihydroxylanost-8-en-3-yl acetate(20905-61-7)
• EPA Substance Registry System: 24,25-dihydroxylanost-8-en-3-yl acetate(20905-61-7)

Safety Data

• Hazardous Substances Data: 20905-61-7(Hazardous Substances Data)

Usage

Main properties

1. Chemical compound
2. Belongs to the group of lanosterols
3. Important intermediate in the biosynthesis of sterols
4. Molecular formula: C30H50O4
5. Consists of a lanosterol molecule with two hydroxyl groups and an acetate group attached

Specific content

1. Involved in various biological processes
2. Includes the synthesis of cholesterol and other important sterols in living organisms
3. Used in pharmacological research to study the effects of sterol derivatives on cellular functions and lipid metabolism
4. Potential applications in the development of new drugs and medical treatments for conditions related to lipid metabolism and cholesterol regulation.

Upstream product

• 10085-27-5 lanosterol-24,25-epoxide-3-O-acetate 
• 18303-41-8 (3S,5R,10S,13R,14R,17R,20R)-24,25-epoxylanosterol 
• 3407-31-6 (24S)-lanosterol epoxide 3-O-acetate 
• 78765-03-4 (10S,13R,14R,17R)-17-((R)-6-hydroxy-6-methyl-5-oxoheptan-2-yl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 2671-68-3 lanosterol 
• 2671-68-3 O-acetyl-lanosterol 
• 79-63-0 tirucallol 

Downstream Products

• 5672-71-9 3β-acetoxy-25,26,27-trinorlanost-8-en-24-al 
• 2671-68-3 O-acetyl-lanosterol 
• 79-63-0 tirucallol 
• 73196-96-0 27-norlanost-8-en-3β-ol 

Relevant articles and documents

Synthesis of Lanostane-Type Triterpenoid N-Glycosides and Their Cytotoxicity against Human Cancer Cell Lines

Seventeen lanostane-type triterpenoid derivatives (2 – 18), including 11N-glycosides (8 – 18), were synthesized from the natural triterpenoid, lanosterol (1), and were evaluated for their cytotoxicity against the human cancer cell lines, HL-60, A549, and MKN45, as well as the normal human lung cells, WI-38. Among them, N-β-d-2-acetamido-2-deoxyglucoside (10) showed cytotoxicity against HL-60, A549, MKN45, and WI-38 cells (IC50 0.0078 – 2.8 μm). However, N-β-d-galactoside (12) showed cytotoxicity against HL-60 and MKN45 cells (IC50 0.0021 – 4.0 μm), but not the normal WI-38 cells. Furthermore, Western blot analysis suggested that 12 induces apoptosis by activation of caspases-3, 8, and 9. These results will be useful for the synthesis of other tetracyclic triterpenoids or steroid N-glycosides to increase their cytotoxicity and apoptosis-inducing activities.

Synthesis, Evaluation, and Structure-Activity Relationship Study of Lanosterol Derivatives to Reverse Mutant-Crystallin-Induced Protein Aggregation

We describe here the development of potent synthetic analogues of the naturally occurring triterpenoid lanosterol to reverse protein aggregation in cataracts. Lanosterol showed superiority to other scaffolds in terms of efficacy and generality in previous studies. Various modified lanosterol derivatives were synthesized via modification of the side chain, ring A, ring B, and ring C. Evaluation of these synthetic analogues draws a clear picture for SAR. In particular, hydroxylation of the 25-position in the side chain profoundly improved the potency, and 2-fluorination further enhanced the biological activity. This work also revealed that synthetic lanosterol analogues could reverse multiple types of mutant-crystallin aggregates in cell models with excellent potency and efficacy. Notably, lanosterol analogues have no cytotoxicity but can improve the viability of the HLE-B3 cell line. Furthermore, representative compound 6 successfully redissolved the aggregated crystallin proteins from the amyloid-like fibrils in a concentration-dependent manner.

Anticancer compound and use thereof

The invention relates to an anticancer medicine which is a lanosterol derivative. The compound has an anticancer effect, and can inhibit the growths of lung cancer cells, liver cells, mammary gland cells, brain cancer cells, and pancreatic cancer cells. The medicine is a compound with a general formula of (I), (II), (III), or (IV). The invention also provides an application of the compound or pharmaceutically acceptable salt thereof in preparing medicines used for treating cancers. The medicine can be used independently, and can be used in combination. Especially, the medicine can be used in combination with gemcitabine or nexavar. The medicine can be used in treating cancers such as lung cancer, liver cancer, pancreatic cancer, breast cancer, brain cancer, and the like.