Isopilosine

Base Information

• Chemical Name: Isopilosine
• CAS No.: 491-88-3
• Molecular Formula: C16H18N2O3
• Molecular Weight: 286.331
• European Community (EC) Number: 207-745-2
• UNII: E82V5ZLP85
• DSSTox Substance ID: DTXSID60878020
• Nikkaji Number: J74.701G
• Wikidata: Q27276987
• ChEMBL ID: CHEMBL524663
• Mol file: 491-88-3.mol

Synonyms:Isopilosine;Carpiline;491-88-3;UNII-E82V5ZLP85;E82V5ZLP85;EINECS 207-745-2;NSC 77211;(3S,4R)-3-[(R)-hydroxy(phenyl)methyl]-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;NSC77211;NSC-77211;(3S,4R)-DIHYDRO-3-((R)-HYDROXYPHENYLMETHYL)-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-2(3H)-FURANONE;(3s,4r)-dihydro-3-[(r)-hydroxyphenylmethyl]-4-[(1-methyl-1h-imidazol-5-yl)methyl]-2(3h)-furanone;CARPIDIN;CARPIDINE;ISOPILOSINE [MI];(+)-ISOPILOSINE;ISOPILOSINE, (+)-;SCHEMBL673285;CHEMBL524663;DTXSID60878020;[3S-[3alpha(S*),4beta]-dihydro-3-(alpha-hydroxybenzyl)-4-[(1-methyl-1H-imidazol-5-yl)methyl]furan-2(3H)-one;BDBM50480316;Q27276987;(3S,4R)-3-[(R)-hydroxy(phenyl)methyl]-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one;(3S,4R)-3-[(R)-hydroxy(phenyl)methyl]-4-[(3-methylimidazol-4-yl)methyl]tetrahydrofuran-2-one;(3S-(3alpha(S*),4beta))-Dihydro-3-(alpha-hydroxybenzyl)-4-((1-methyl-1H-imidazol-5-yl)methyl)furan-2(3H)-one;2(3H)-FURANONE, DIHYDRO-3-((R)-HYDROXYPHENYLMETHYL)-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, (3S,4R)-;2(3H)-Furanone, dihydro-3-[(R)-(hydroxyphenylmethyl)-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S,4R)

Chemical Property of Isopilosine

Chemical Property:

• Melting Point: 182-182.5°
• Refractive Index: 1.6320 (estimate)
• Boiling Point: 428.69°C (rough estimate)
• PKA: 13.59±0.20(Predicted)
• Flash Point: 297.5oC
• PSA: 64.35000
• Density: 1.1190 (rough estimate)
• LogP: 1.48540
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 286.13174244
• Heavy Atom Count: 21
• Complexity: 371

Purity/Quality:

98%min ^*data from raw suppliers

ISOPILOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC=C1CC2COC(=O)C2C(C3=CC=CC=C3)O
• Isomeric SMILES: CN1C=NC=C1C[C@H]2COC(=O)[C@@H]2[C@H](C3=CC=CC=C3)O
• Description: A minor alkaloid of Pilocarpus rnicrophyllus which has recently been discovered together with the following base. The structure has been established from the infrared, NMR and mass spectra.

Technology Process of Isopilosine

There total 2 articles about Isopilosine 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:

(3S)-3r-benzoyl-4t-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one (38993-87-2) → (3S)-3r-((S)-hydroxy-phenyl-methyl)-4t-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one (38993-92-9) + pilosine (491-88-3)

Guidance literature:

With hydrogen; platinum; In ethanol;

DOI:10.1002/hlca.19720550402

Reference yield:

→ pilosine (491-88-3)

Guidance literature:

Reference yield:

pilosine (491-88-3) → pilocarpine (92-13-7)

Guidance literature:

Multi-step reaction with 3 steps

2: KOtBu / butan-1-ol / Heating

3: (i) H₂, PtO₂-C, MeOH, (ii) Ac₂O, AcOH, (iii) H₂, PtO₂, MeOH

With potassium tert-butylate; In butan-1-ol;

DOI:10.1002/hlca.19720550402

upstream raw materials:

(3S)-3r-benzoyl-4t-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one

Downstream raw materials:

(R)-3-((Ξ)-benzylidene)-4-(3-methyl-3H-imidazol-4-ylmethyl)-dihydro-furan-2-one; anhydropilosine

(+)-pilosinine

Epiiso-p-fluorpilosin

o-Fluorepiisopilosin

Refernces