54274-72-5

Basic information

• Product Name: 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)
• Synonyms: 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)
• CAS NO: 54274-72-5
• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.58
• Mol File: 54274-72-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)(54274-72-5)
• EPA Substance Registry System: 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)- (9CI)(54274-72-5)

Safety Data

• Hazardous Substances Data: 54274-72-5(Hazardous Substances Data)

Usage

Uses

Sclareol Diacetate is an intermediate in the synthesis of (E)-Labd-13-ene-8,15-diol compounds with antiviral and anticancer activities and has been the most effective growth inhibitor of murine leukemia cell lines P388.

Upstream product

• 515-03-7 sclareol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 10314-42-8 isomanool 
• 1164151-92-1 labda-7,14-dien-13(R)-ol 
• 596-85-0 manool 
• 515-03-7 sclareol 
• 22628-62-2 8α-acetoxy-13R-hydroxy-labda-14-ene 
• 1153-34-0 epi-8-ambracetal 
• 1153-34-0 ambracetal 
• 1153-34-0 epiambraketal 
• 468-84-8 ambreinolide 
• 6790-58-5 (-)-ambroxide 
• 38419-77-1 (4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene 
• 150267-49-5 (1R,2R,4aS,8aS)-1-(2-(benzyloxy)ethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol 
• 10207-79-1 ent-8α-hydroxy-labda-13(16),14-dien 
• 3649-91-0 8,15-dihydroxy-13E-labdane 

Relevant articles and documents

A short and practical synthesis of (+)-amberketal and (-)-epi-8-amberketal from natural (-)-sclareol

Starting from natural (-)-sclareol (4,) (+)-amberketal (9) and (-)-epi-8-amberketal (10) have been synthesized regioselectively in 4 (24% overall yield) and 5 steps (7% overall yield) respectively, by passing through the same unpurified key intermediate 7b.

Antischistosomal Properties of Sclareol and Its Heck-Coupled Derivatives: Design, Synthesis, Biological Evaluation, and Untargeted Metabolomics

Sclareol, a plant-derived diterpenoid widely used as a fragrance and flavoring substance, is well-known for its promising antimicrobial and anticancer properties. However, its activity on helminth parasites has not been previously reported. Here, we show that sclareol is active against larval (IC50 ≈ 13 μM), juvenile (IC50 = 5.0 μM), and adult (IC50 = 19.3 μM) stages of Schistosoma mansoni, a parasitic trematode responsible for the neglected tropical disease schistosomiasis. Microwave-assisted synthesis of Heck-coupled derivatives improved activity, with the substituents choice guided by the Matsy decision tree. The most active derivative 12 showed improved potency and selectivity on larval (IC50 ≈ 2.2 μM, selectivity index (SI) ≈ 22 in comparison to HepG2 cells), juvenile (IC50 = 1.7 μM, SI = 28.8), and adult schistosomes (IC50 = 9.4 μM, SI = 5.2). Scanning electron microscopy studies revealed that compound 12 induced blebbing of the adult worm surface at sublethal concentration (12.5 μM); moreover, the compound inhibited egg production at the lowest concentration tested (3.13 μM). The observed phenotype and data obtained by untargeted metabolomics suggested that compound 12 affects membrane lipid homeostasis by interfering with arachidonic acid metabolism. The same methodology applied to praziquantel (PZQ)-treated worms revealed sugar metabolism alterations that could be ascribed to the previously reported action of PZQ on serotonin signaling and/or effects on glycolysis. Importantly, our data suggest that compound 12 and PZQ exert different antischistosomal activities. More studies will be necessary to confirm the generated hypothesis and to progress the development of more potent antischistosomal sclareol derivatives.

A short and efficient synthesis of (+)-totarol

A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1. ARKAT-USA, Inc.