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:

99.9% ^*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
• Uses: (1) It is mainly used for the synthesis of ambergris-amber fragrance, and more suitable for perfume and essence when utilizing its aroma-retaining ability for blending. (2) It is also used for flavor, spices, cigarettes, cosmetics, health food, food additives. Sclareol is used in biological studies as it has anti-inflammatory activity in both lipopolysaccharide-stimulated macophages and λ-carrageenan-induced paw edema model. Sclareol may be used as a starting material in the synthesis of ambergris fragrance chemicals such as ambraoxide, ambrox, methylambraoxide, ambracetal, ambraketal and epiambraketal. It may also be used in the synthesis of (+)-galanolactone, (-)-8-epi-galanolactone and (+)-labdienedial.

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:

(-)-ambroxide

labda-8(17),13E/Z-diene

manool

sclareol oxide

Refernces

• 1、 Rogachev, Victor,Loehl, Thorsten,Markert, Thomas,Metz, Peter. "A short and efficient synthesis of (+)-totarol". . p. 172 - 180. Retrieved 2013/09/24.
• 2、 Leite, Mary Ann F.,Sarragiotto, Maria Helena,Imamura, Paulo M.,Marsaioli, Anita J.. "Absolute Configuration of Drim-9(11)-en-8-ol from Aspergillus oryzae". . p. 5409 - 5410. Retrieved 2007/10/02.