Sclareol

Base Information

• Chemical Name: Sclareol
• CAS No.: 515-03-7
• Deprecated CAS: 17904-64-2,886030-32-6,886030-32-6
• Molecular Formula: C20H36O2
• Molecular Weight: 308.505
• Hs Code.: 29061990
• European Community (EC) Number: 208-194-0
• UNII: B607NP0Q8Y
• DSSTox Substance ID: DTXSID0047111
• Nikkaji Number: J13.989K
• Wikipedia: Sclareol
• Wikidata: Q796619
• Metabolomics Workbench ID: 28503
• ChEMBL ID: CHEMBL294740
• Mol file: 515-03-7.mol

Synonyms:labd-14-ene-8alpha, 13beta-diol;sclareol;sclareol oxide

Chemical Property of Sclareol

Chemical Property:

• Appearance/Colour: white fine powder
• Vapor Pressure: 5.36E-08mmHg at 25°C
• Melting Point: 95-100 °C
• Refractive Index: 1.489
• Boiling Point: 398.265 °C at 760 mmHg
• PKA: 14.49±0.29(Predicted)
• Flash Point: 169.112 °C
• PSA: 40.46000
• Density: 0.954 g/cm³
• LogP: 4.69720
• Storage Temp.: 2-8°C
• Solubility.: Chlorform, Ethyl Acetate (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 308.271530387
• Heavy Atom Count: 22
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

Sclareol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC(C2CCC(C)(C=C)O)(C)O)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]([C@@H]2CC[C@](C)(C=C)O)(C)O)(C)C
• General Description: Sclareol is a plant-derived diterpenoid with demonstrated antimicrobial and anticancer properties, which also exhibits significant anti-schistosomal activity against *Schistosoma mansoni* at various life stages. Its mechanism of action differs from the standard drug praziquantel (PZQ), and metabolomic studies suggest that its derivatives, particularly compound 12, disrupt membrane lipid homeostasis by interfering with arachidonic acid metabolism and altering sugar metabolism. These findings highlight its potential as a lead compound for developing novel anti-schistosomal agents.

Technology Process of Sclareol

There total 11 articles about Sclareol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

pinnatol A (78012-27-8,94903-99-8,94904-00-4,98719-41-6,110269-55-1,110269-56-2,144069-45-4) → (1R,2R,4aR,8aR)-1-((R)-3-Hydroxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (515-03-7,1232-00-4,4630-08-4,74638-09-8,74638-15-6,86023-49-6,86023-50-9,98719-42-7)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; for 10h; Heating;

DOI:10.1246/cl.1985.1259

Reference yield: 60.0%

(R)-5-((1R,2R,4aS,8aS)-2-acetoxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl acetate (54274-72-5) → sclareol (515-03-7) + 8α-acetoxy-13R-hydroxy-labda-14-ene (22628-62-2)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 15 - 20 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.3998/ark.5550190.0013.313

Reference yield:

labd-13E-en-8α,15-diol diphosphate (1000876-36-7) → sclareol (515-03-7)

Guidance literature:

With N glutinosa sclareol synthase NgSs₃; In aq. buffer; at 28 ℃; Catalytic behavior; Enzymatic reaction;

upstream raw materials:

(1R,2R,4aS,8aS)-1-(3-Hydroperoxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

8α,20α-Epoxy-manool

manool

8,17-epoxy-14-labden-13-ol

Downstream raw materials:

15-nor-8α,13-dihydroxy-14-labdanoic acid

(13Ξ)-8,13-epoxy-labdan-15-oic acid methyl ester

(±)-sclareolide

(R)-5-((1R,2R,4aS,8aS)-2-acetoxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl acetate

Refernces

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

10.1021/acsinfecdis.9b00034

This study investigated the anti-schistosomal properties of sclareol, a plant-derived diterpenoid, and its Heck-coupled derivatives against Schistosoma mansoni, a parasitic trematode that causes schistosomiasis. Sclareol, known for its antimicrobial and anticancer properties, is active against the larval, juvenile, and adult stages of S. mansoni. The researchers synthesized a series of sclareol derivatives guided by Matsy decision trees to improve their anthelmintic activity. The most potent derivative, compound 12, showed enhanced potency and selectivity against schistosomes. The study aimed to understand the mechanism of action of sclareol, which is different from that of the standard anti-schistosomal drug praziquantel (PZQ). Metabolomic analysis revealed that compound 12 affects membrane lipid homeostasis by interfering with arachidonic acid metabolism, primarily altering sugar metabolism. These findings provide insights into the development of more effective anti-schistosomal sclareol derivatives.

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