Isocupressic acid

Base Information

• Chemical Name: Isocupressic acid
• CAS No.: 1909-91-7
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• UNII: 6DV5EL78HE
• DSSTox Substance ID: DTXSID901045341
• Nikkaji Number: J1.271.001A,J148.791D
• Wikipedia: Isocupressic_acid
• Wikidata: Q15426267
• Metabolomics Workbench ID: 140981
• ChEMBL ID: CHEMBL511193
• Mol file: 1909-91-7.mol

Synonyms:15-hydroxylabda-8(17),13-dien-19-oic acid;isocupressic acid

Chemical Property of Isocupressic acid

Chemical Property:

• Vapor Pressure: 3.71E-10mmHg at 25°C
• Melting Point: 109-110 °C
• Boiling Point: 454.2°Cat760mmHg
• PKA: 4.68±0.60(Predicted)
• Flash Point: 242.6°C
• PSA: 57.53000
• Density: 1.06g/cm³
• LogP: 4.56870
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

98%Min ^*data from raw suppliers

Isocupressicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCO)CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• Isomeric SMILES: C/C(=C\CO)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C
• Uses: Isocupressic Acid inhibits proliferation and induces cell cycle arrest and apoptosis in ovarian cancer cells. It is also associated with spontaneous abortion in cattle after consumption of conifer needles.

Technology Process of Isocupressic acid

There total 1 articles about Isocupressic 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:

cryptomeridiol-4-yl-19-acetoxylabda-8(17),13E-dien-19-oate → isocupressic acid (69308-72-1,77096-82-3,1909-91-7) + cryptomeridiol (55353-16-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1016/S0031-9422(00)89538-2

Reference yield: 91.0%

benzyl bromide (100-39-0) + isocupressic acid (69308-72-1,77096-82-3,1909-91-7) → C27H38O3

Guidance literature:

With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201602476

Reference yield:

isocupressic acid (69308-72-1,77096-82-3,1909-91-7) → strongylophorine 8

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium carbonate / dichloromethane; N,N-dimethyl-formamide / 24 h / 0 °C / Inert atmosphere

2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 24.5 h / 0 - 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / 760.05 Torr / Inert atmosphere

5.1: ammonium bicarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole; triethylamine / dichloromethane; N,N-dimethyl-formamide / 72 h / 0 - 20 °C / Inert atmosphere

6.1: iodine; lead(IV) tetraacetate / benzene / 20 h / 20 °C / Irradiation; Inert atmosphere

7.1: potassium hydroxide / methanol / 2 h / Reflux; Inert atmosphere

8.1: hydrogenchloride / acetonitrile; water / 4 h / 100 °C / Reflux; Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethyl acetate / 12 h / 40 °C / Inert atmosphere

10.1: sodium iodide; chloro-trimethyl-silane / toluene; acetonitrile / 18 h / 40 °C / Inert atmosphere

11.1: oxygen / dichloromethane / 0.5 h / 20 °C / 760.05 Torr / Inert atmosphere

11.2: 1 h / 20 °C / 760.05 Torr / Inert atmosphere

With hydrogenchloride; chloro-trimethyl-silane; 1-hydroxy-7-aza-benzotriazole; tributylphosphine; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; iodine; oxygen; lead(IV) tetraacetate; ammonium bicarbonate; potassium carbonate; acetic acid; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; potassium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/anie.201602476

Downstream raw materials:

acetyl isocupressic acid

agathic acid

dihydroagathic acid

agathadiol

Refernces