Ajulemic acid

Base Information

• Chemical Name: Ajulemic acid
• CAS No.: 137945-48-3
• Molecular Formula: C25H36O4
• Molecular Weight: 400.558
• UNII: OGN7X90BT8
• DSSTox Substance ID: DTXSID40900959
• Nikkaji Number: J491.775H
• Wikipedia: Ajulemic_acid
• Wikidata: Q3604498
• NCI Thesaurus Code: C174799
• Pharos Ligand ID: ZVWVYX1MHJN2
• Metabolomics Workbench ID: 153226
• ChEMBL ID: CHEMBL456341
• Mol file: 137945-48-3.mol

Synonyms:(6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-(2-methyl-2-octanyl)-6a,7,8,10a-tetrahydro-6H-benzo(c)chromene-9-carboxylic acid;ajulemic acid;IP 751;IP-751;lenabasum;resunab

Chemical Property of Ajulemic acid

Chemical Property:

• Vapor Pressure: 1.2E-10mmHg at 25°C
• Melting Point: 112-114° (sintering)
• Refractive Index: 1.535
• Boiling Point: 495.7 °C at 760 mmHg
• PKA: 4.75±0.40(Predicted)
• Flash Point: 158.5 °C
• PSA: 66.76000
• Density: 1.085 g/cm³
• LogP: 6.31580
• XLogP3: 7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 400.26135963
• Heavy Atom Count: 29
• Complexity: 620

Purity/Quality:

98%Min ^*data from raw suppliers

IP-751 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(C)(C)C1=CC(=C2C3CC(=CCC3C(OC2=C1)(C)C)C(=O)O)O
• Isomeric SMILES: CCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)C(=O)O)O
• Recent ClinicalTrials: Safety, Tolerability, and Efficacy of JBT-101 in Subjects With Dermatomyositis
• Recent EU Clinical Trials: An Observational Long-Term Safety Surveillance of Participants from Corbus Sponsored Lenabasum Pivotal Clinical Trials
• Recent NIPH Clinical Trials: JBT101-DM-002 A Phase 3 safety and efficacy study of lenabasum in dermatomyositis subjects

Technology Process of Ajulemic acid

There total 9 articles about Ajulemic acid 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: 93.0%

(6aR,10aR)-1-acetoxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid (137945-50-7) → ajulemic acid (137945-48-3)

Guidance literature:

With water; sodium hydroxide; In tert-butyl methyl ether; at 45 - 55 ℃; for 1.5h;

Reference yield: 56.0%

(6aR,10aR)-1-((tert-butyldimethylsilyl)oxy)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid (137945-49-4) → ajulemic acid (137945-48-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/jm00095a007

Reference yield: 20.0%

(6aR,10aR)-3-(1',1'-dimethylheptyl)-Δ8-tetrahydrocannabinol 1-O-acetate (61597-29-3) → ajulemic acid (137945-48-3)

Guidance literature:

(6aR,10aR)-3-(1',1'-dimethylheptyl)-Δ⁸-tetrahydrocannabinol 1-O-acetate; With selenium(IV) oxide; In tetrahydrofuran; water; at 55 ℃; for 21h; Large scale;

With dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 25 ℃; for 13.5h; Large scale;

With water; sodium hydroxide; In tetrahydrofuran; at 5 - 25 ℃; for 15h; Large scale;

upstream raw materials:

(6aR,10aR)-1-((tert-butyldimethylsilyl)oxy)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid

2,2-Dimethyl-propionic acid (6aR,10aR)-3-(1,1-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester

[(6aR,10aR)-1-(tert-Butyl-dimethyl-silanyloxy)-3-(1,1-dimethyl-heptyl)-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-yl]-methanol

(6aR,10aR)-1-(tert-Butyl-dimethyl-silanyloxy)-3-(1,1-dimethyl-heptyl)-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carbaldehyde

Downstream raw materials:

(6aR,10aR)-1-((tert-butyldimethylsilyl)oxy)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid

Refernces

• 1、 Tepper, Mark A.,Zurier, Robert B.,Burstein, Sumner H.. "Ultrapure ajulemic acid has improved CB2 selectivity with reduced CB1 activity". . p. 3245 - 3251. Retrieved 2014.
• 2、 -. "ULTRAPURE TETRAHYDROCANNABINOL-11-OIC ACIDS". Page/Page column 24; 25. . Retrieved 2014/09/03.