beta-Santonin

Base Information

• Chemical Name: beta-Santonin
• CAS No.: 481-07-2
• Molecular Formula: C15H18O3
• Molecular Weight: 246.306
• NSC Number: 41311
• DSSTox Substance ID: DTXSID901121272
• Nikkaji Number: J12.330G
• Wikidata: Q27103654
• Metabolomics Workbench ID: 28283
• Mol file: 481-07-2.mol

Synonyms:beta-Santonin;481-07-2;Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3R-(3alpha,3abeta,5aalpha,9balpha))-;.beta.-Santonin;SANTONIN, BETA;SCHEMBL16670766;CHEBI:28356;DTXSID901121272;NSC41311;NSC-41311;LMPR0103190004;(3R,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione;C09545;Q27103654;(3R,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione

Chemical Property of beta-Santonin

Chemical Property:

• Vapor Pressure: 2.24E-07mmHg at 25°C
• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 189.7°C
• PSA: 43.37000
• Density: 1.18g/cm³
• LogP: 2.41960
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 500

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C=CC(=O)C(=C3C2OC1=O)C)C
• Isomeric SMILES: C[C@@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C

Technology Process of beta-Santonin

There total 92 articles about beta-Santonin 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:

hydrogenchloride (7647-01-0,15364-23-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) + α-Santonin (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9) → (+/-)-α-Desmotroposantonin (438-50-6,13743-88-9,13743-89-0,13743-96-9,16963-59-0,21142-64-3,5951-46-2) + (+/-)-Santonin-C (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9)

Guidance literature:

Reference yield:

rac-11-methyl-3-oxo-eudesm-4-ene-12,13-dioic acid diethyl ester (102315-35-5) → (+/-)-Santonin-D (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9)

Guidance literature:

Multi-step reaction with 7 steps

1: aq.-ethanolic KOH

2: diethyl ether; bromine

3: aqueous sodium hydrogencarbonate solution

4: diethyl ether; bromine

5: 5-ethyl-2-methyl-pyridine

6: aqueous KOH-solution / Erwaermen der Reaktionsloesung mit wss. Salzsaeure

7: 2,4,6-trimethyl-pyridine

With 2,4,6-trimethyl-pyridine; 5-ethyl-2-methyl-pyridine; potassium hydroxide; diethyl ether; bromine; sodium hydrogencarbonate;

Reference yield:

rac-(11R)-2ξ,6ξ-dibromo-3-oxo-eudesm-4-en-12-oic acid → (+/-)-Santonin-D (481-06-1,481-07-2,1618-77-5,1618-78-6,3650-48-4,21295-21-6,64912-47-6,64912-48-7,135270-27-8,135270-28-9)

Guidance literature:

With lutidine;

DOI:10.1246/bcsj.27.7

upstream raw materials:

2,4,6-trimethyl-pyridine

(11R)-2ξ-bromo-6α-hydroxy-3-oxo-7βH-eudesm-4-en-12-oic acid-lactone

ent-(11R)-2ξ-bromo-6β-hydroxy-3-oxo-eudesm-4-en-12-oic acid-lactone

rac-(11S)-2ξ-bromo-6β-hydroxy-3-oxo-eudesm-4-en-12-oic acid-lactone

Downstream raw materials:

(11R)-3α,6α-dihydroxy-eudesman-12-oic acid-6-lactone

(11R)-6α-hydroxy-3-oxo-5β-eudesman-12-oic acid-lactone

tetrahydro-β-santonin

Cadabicilone