Sclareolide

Base Information

• Chemical Name: Sclareolide
• CAS No.: 564-20-5
• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.381
• Hs Code.: 29322090
• European Community (EC) Number: 209-269-0
• UNII: 37W4O0O6E6
• DSSTox Substance ID: DTXSID8047686
• Nikkaji Number: J69.947K
• Wikipedia: Sclareolide
• Wikidata: Q105115731
• RXCUI: 1426934
• Metabolomics Workbench ID: 130131
• ChEMBL ID: CHEMBL304461
• Mol file: 564-20-5.mol

Synonyms:sclareolide

Chemical Property of Sclareolide

Chemical Property:

• Appearance/Colour: off-white to white crystal powder
• Vapor Pressure: 0.000299mmHg at 25°C
• Melting Point: 124-126 °C
• Refractive Index: 1.489
• Boiling Point: 321.4 °C at 760 mmHg
• Flash Point: 132.4 °C
• PSA: 26.30000
• Density: 1.009 g/cm³
• LogP: 3.93460
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility.: 10mg/L at 25℃
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 250.193280068
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

99%, ^*data from raw suppliers

Sclareolide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CC(=O)O3)C)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC(=O)O3)C)(C)C
• Uses: Sclareolide is found in Salvia yosgadensis and is a close analog of sclareol, an antifungal diterpene. antimicrobial sclareolide is a fragrancing ingredient, it can help mask formulation odors. It is synthetically manufactured.

Technology Process of Sclareolide

There total 164 articles about Sclareolide 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: 99.0%

2-((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)propan-2-ol (145511-21-3) → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With sodium chromate(VI); sodium acetate; acetic anhydride; acetic acid; In benzene; at 40 ℃; for 5h;

DOI:10.1016/S0040-4020(01)92289-6

Reference yield: 97.0%

12(R,S)-15-Acetoxy-8,12 epoxylabdane → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With sodium chromate(VI); sodium acetate; acetic anhydride; In acetic acid; at 30 - 40 ℃; for 12h;

DOI:10.1016/S0040-4020(01)88343-5

Reference yield: 95.0%

8α,13(S)-epoxy-15-nor-labdan-14-al (52104-92-4) → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With peracetic acid; at 50 - 55 ℃;

DOI:10.1081/SCC-100103265

upstream raw materials:

(1R,2R,4aS,8aS)-(2-hydroxy-2,5,5,8a-tetramethylperhydronaphthyl)acetic acid

Ambrein

14,15-bisnor-8α,12S-epoxylabdan-13-one

cis-abienol

Downstream raw materials:

(1R,2R,3aS,7aS)-2,4,4,7a-Tetramethyl-1-(3-oxo-butyl)-octahydro-indene-2-carboxylic acid

(-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one

1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol

Refernces

Synthesis of Cyclosiphonodictyol A and Its Bis(sulfato)

10.1021/acs.joc.9b03434

The study reports the first synthesis of cyclosiphonodictyol A (11) and its bis(sulfato) derivative (12) from the commercially available lactone (+)-sclareolide (17). The synthetic sequence involves 11 steps with a global yield of 46%. Key steps include the nucleophilic attack of a hindered tertiary alkoxide, a ring-closing metathesis reaction, and the Diels-Alder cycloaddition of a dienol acetate. The synthesis begins with the conversion of (+)-sclareolide (17) to alcohol 16, which is then converted to oxy-ester 21 using bromo ester 20 as an alkylating agent. The oxepane ring is formed via ring-closing metathesis of ester 21 to give ester 22. Subsequent transformations involve the conversion of ester 22 to ketone 14, followed by the construction of the aromatic ring through a series of reactions involving trans-1,2-bis(phenylsulfonyl)ethylene and isopropenyl acetate to form cycloadducts 24, which are then converted to acetate 25 and finally to phenol 13. Phenol 13 is oxidized to quinone 26 and subsequently reduced to cyclosiphonodictyol A (11). Compound 11 is then converted to its bis(sulfato) derivative (12) through successive treatments with pyridine-sulfur trioxide and Na2CO3. The synthesized compounds exhibit similar NMR data to the natural products, confirming their structures.