Vulgarin

Base Information

• Chemical Name: Vulgarin
• CAS No.: 3162-56-9
• Deprecated CAS: 5091-07-6,1351-48-0,17237-80-8,34319-09-0
• Molecular Formula: C15H20 O4
• Molecular Weight: 264.321
• European Community (EC) Number: 803-488-0
• DSSTox Substance ID: DTXSID30928884
• Nikkaji Number: J14.792C
• Wikidata: Q27108555
• Metabolomics Workbench ID: 123469
• ChEMBL ID: CHEMBL1422618
• Mol file: 3162-56-9.mol

Synonyms:judaicin (eudesmane naphthofuran);judaicin, (3S-(3alpha,3aalpha,5abeta,9alpha,9aalpha,9bbeta))-isomer

Chemical Property of Vulgarin

Chemical Property:

• Vapor Pressure: 5.51E-10mmHg at 25°C
• Melting Point: 240-243 °C
• Boiling Point: 449.9°Cat760mmHg
• PKA: 13.15±0.60(Predicted)
• Flash Point: 168.9°C
• PSA: 63.60000
• Density: 1.2g/cm³
• LogP: 1.47030
• Storage Temp.: ?20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 483

Purity/Quality:

97% ^*data from raw suppliers

Vulgarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C(C2OC1=O)C(C=CC3=O)(C)O)C
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)[C@](C=CC3=O)(C)O)C
• Uses: Vulgarin is a sesquiterpene lactone and is used in traditional Chinese medicine in the treatment of hypertension.

Technology Process of Vulgarin

There total 11 articles about Vulgarin 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: 77.0%

11,13-didehydrovulgarin (16981-97-8) → vulgarin (3162-56-9,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

With Cunnighamella blakesleeana; In water; acetone; for 336h; Reagent/catalyst; stereoselective reaction; Microbiological reaction;

DOI:10.1002/cbdv.201700211

Reference yield: 27.0%

1α-hydroxy-5α,6β,7α,11βH-eudesm-3-en-6,13-olide (16886-42-3) → vulgarin (3162-56-9,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

With jones reagent; In acetone; for 4h; Ambient temperature;

Reference yield: 25.0%

Deoxyvulgarin (3650-22-4) → vulgarin (3162-56-9,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

With jones reagent; In acetone; for 4h; Ambient temperature;

upstream raw materials:

methanol

Acetic acid (6Z,8Z,10E)-(3S,3aS,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,11a-hexahydro-cyclodeca[b]furan-7-yl ester

Peroxyvulgarin

(11S)-3α,4α-Epoxy-1oxoeudesmano-13,6α-lactone

Downstream raw materials:

1-p-toluenesulfonyloxy-eudesman-3-en-6,12-olide

11,13-dihydrosantamarin

1-p-toluenesulfonyloxy-5-hydroxy-eudesman-3-en-6,12-olide

C₂₂H₃₀N₂O₄S

Refernces

• 1、 Hernandez,Afonso,Gonzalez,Galindo. "Partial synthesis of germacranolides with pyran and furan-type rings". . p. 4747 - 4750. Retrieved 2007/10/02.
• 2、 Al-Said, Mansour S.,Khalifa, Sherief I.,El-Feraly, Farouk S.,Hufford, Charles D.. "BIOGENETIC-TYPE SYNTHESIS OF VULGARIN AND PEROXYVULGARIN". . p. 107 - 108. Retrieved 2007/10/02.