Eucannabinolide

Base Information

• Chemical Name: Eucannabinolide
• CAS No.: 38458-58-1
• Molecular Formula: C22H28O8
• Molecular Weight: 420.46
• ChEMBL ID: CHEMBL4168503
• DSSTox Substance ID: DTXSID701098813
• Nikkaji Number: J16.510G
• Wikidata: Q27106876
• Mol file: 38458-58-1.mol

Synonyms:Eucannabinolide;Hiyodorilactone A;38458-58-1;MEGxp0_000031;CHEBI:5740;CHEMBL4168503;DTXSID701098813;AKOS040761712;NCGC00385050-01;C09475;Q27106876;(E)-4-Hydroxy-2-hydroxymethyl-2-butenoic acid(3ar,4r,6e,9s,10z,11ar)-9-acetoxy-2,3,3a,4,5,8,9,11a-octahydro-6,10-dimethyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester;2-Butenoic acid, 4-hydroxy-2-(hydroxymethyl)-, (3aR,4R,6E,9S,10Z,11aR)-9-(acetyloxy)-2,3,3a,4,5,8,9,11a-octahydro-6,10-dimethyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester, (2E)-

Chemical Property of Eucannabinolide

Chemical Property:

• Vapor Pressure: 6.61E-18mmHg at 25°C
• Boiling Point: 618.9°C at 760 mmHg
• Flash Point: 211.5°C
• PSA: 119.36000
• Density: 1.26g/cm³
• LogP: 1.52510
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 420.17841785
• Heavy Atom Count: 30
• Complexity: 804

Purity/Quality:

99% ^*data from raw suppliers

Eucannabinolide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(C(=CC2C(C(C1)OC(=O)C(=CCO)CO)C(=C)C(=O)O2)C)OC(=O)C
• Isomeric SMILES: C/C/1=C\C[C@@H](/C(=C\[C@@H]2[C@@H]([C@@H](C1)OC(=O)/C(=C/CO)/CO)C(=C)C(=O)O2)/C)OC(=O)C

Technology Process of Eucannabinolide

There total 23 articles about Eucannabinolide 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: 54.0%

2,2-Dimethyl-4,7-dihydro-[1,3]dioxepine-5-carboxylic acid (6E,10Z)-(3aR,4R,9S,11aS)-9-acetoxy-6,10-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-4-yl ester → germacranolide eucannabinolide (38458-58-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; ethylene glycol;

DOI:10.1021/ja00341a055

Reference yield:

(3Z,7E)-(1S,5S,10S)-5-Benzyloxymethoxy-4,8-dimethyl-bicyclo[8.2.0]dodeca-3,7-diene-2,11-dione → germacranolide eucannabinolide (38458-58-1)

Guidance literature:

Multi-step reaction with 15 steps

1: H₂O₂, Ti(O-i-Pr)4, i-Pr₂NEt / diethyl ether / 0.25 h / -30 °C

2: NaBH₄ / methanol / 0.5 h / 0 °C

3: 61 percent / K₂CO₃ / methanol / 5 h / 25 °C

4: 71 percent / Collins reagent / CH₂Cl₂ / 0.08 h / 25 °C

5: 70 percent / DBU / tetrahydrofuran / 3 h / 25 °C

6: 93 percent / NaBH₄ / methanol

7: 78 percent / H₂ / 20percent Pd(OH)2/C / aq. ethanol / 25 °C / 1137.7 Torr

8: C₅H₅N / CH₂Cl₂ / 25 °C

9: 1.) LDA / 1.) THF, 2.) -70 deg C

10: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 25 °C

11: DBU / dioxane / 0.5 h / 70 °C

12: Bu₄NF / tetrahydrofuran / 25 °C

13: 82 percent / DCC, 4-pyrrolidinopyridine

14: 52 percent / DCC, 4-pyrrolidinopyridine

15: 54 percent / C₅H₅NH⁺OTs^- / methanol; ethane-1,2-diol

With pyridine; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; 4-pyrrolidin-1-ylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethylene glycol;

DOI:10.1021/ja00341a055

Reference yield:

(5Z,9E)-(3aS,7S,11aS)-7-Benzyloxymethoxy-6,10-dimethyl-3,3a,7,8,11,11a-hexahydro-cyclodeca[b]furan-2,4-dione (84066-35-3) → germacranolide eucannabinolide (38458-58-1)

Guidance literature:

Multi-step reaction with 14 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: 61 percent / K₂CO₃ / methanol / 5 h / 25 °C

3: 71 percent / Collins reagent / CH₂Cl₂ / 0.08 h / 25 °C

4: 70 percent / DBU / tetrahydrofuran / 3 h / 25 °C

5: 93 percent / NaBH₄ / methanol

6: 78 percent / H₂ / 20percent Pd(OH)2/C / aq. ethanol / 25 °C / 1137.7 Torr

7: C₅H₅N / CH₂Cl₂ / 25 °C

8: 1.) LDA / 1.) THF, 2.) -70 deg C

9: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 25 °C

10: DBU / dioxane / 0.5 h / 70 °C

11: Bu₄NF / tetrahydrofuran / 25 °C

12: 82 percent / DCC, 4-pyrrolidinopyridine

13: 52 percent / DCC, 4-pyrrolidinopyridine

14: 54 percent / C₅H₅NH⁺OTs^- / methanol; ethane-1,2-diol

With pyridine; dmap; sodium tetrahydroborate; Collins oxidation agent; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; 4-pyrrolidin-1-ylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethylene glycol;

DOI:10.1021/ja00341a055

upstream raw materials:

(6E,10Z)-(3aR,4R,9S,11aS)-4,9-Dihydroxy-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

3β-acetoxy-8β-hydroxycostunolide

methyl (E)-2-methyl-2-butenoate

Methyl-2(Z)-4-brom-2-brommethyl-2-butenoat

Downstream raw materials:

8-Deacyleucannabinolide

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