Atractylenolide I

Base Information

• Chemical Name: Atractylenolide I
• CAS No.: 73069-13-3
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.307
• DSSTox Substance ID: DTXSID901316467
• Nikkaji Number: J11.963F
• Metabolomics Workbench ID: 134744
• ChEMBL ID: CHEMBL449520
• Mol file: 73069-13-3.mol

Synonyms:8,9-dehydroasterolide;atractylenolide I

Chemical Property of Atractylenolide I

Chemical Property:

• Vapor Pressure: 9.08E-07mmHg at 25°C
• Melting Point: 121-123 °C(Solv: ligroine (8032-32-4))
• Refractive Index: 1.554
• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 170.8 °C
• PSA: 26.30000
• Density: 1.12 g/cm³
• LogP: 3.50990
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble1mg/mL, clear, colorless
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 230.130679813
• Heavy Atom Count: 17
• Complexity: 481

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Atractylenolide I ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2CC3C(=C)CCCC3(C=C2OC1=O)C
• Isomeric SMILES: CC1=C2C[C@H]3C(=C)CCC[C@@]3(C=C2OC1=O)C
• Description: Atractylenolide I is a sesquiterpene that has been found in the rhizomes of A. macrocephala and has diverse biological activities, including anti-inflammatory, anti-angiogenic, anti-tumor, and antidepressant properties. It inhibits LPS-induced increases in TNF-α and nitric oxide (NO) production, as well as inducible nitric oxide synthase (iNOS) activity, in murine peritoneal macrophages (IC50s = 23.1, 41, and 67.3 μM, respectively). Atractylenolide I reduces pouch fluid weight, inflammatory cell count, granuloma weight, and vascular index (ID50s = 24.18, 19.46, 14.44, and 15.15 mg/kg, respectively) in a mouse air pouch granuloma model induced by Freund''s complete adjuvant (FCA). It also reduces the number of microvessels in the air pouch wall by 58.27% when administered at a dose of 20 mg/kg and reduces the blood levels of TNF-α, IL-1β, IL-6, VEGF, placenta growth factor (PlGF), and bFGF in a dose-dependent manner in a mouse model of FCA-induced granuloma. Atractylenolide I inhibits the growth of T-24, 5637, RT4, and 253J bladder cancer cells in vitro (IC50s = 12.8-63.7 μM) and reduces tumor growth in T-24 and 253J mouse xenograft models in a dose-dependent manner. In a mouse model of depression induced by chronic unpredictable mild stress, atractylenolide I reverses stress-induced decreases in hippocampal levels of serotonin (5-HT; ) and norepinephrine and reduces immobility time in the forced swim and tail suspension tests in a dose-dependent manner, indicating antidepressant-like activity.

Technology Process of Atractylenolide I

There total 26 articles about Atractylenolide I 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: 66.0%

(4aα,8aβ,8α,9aβ)-4a,5,6,7,8,8a,9,9a-Octahydro-9-hydroxy-3,8a-dimethyl-5-methylennaphtho<2,3-b>furan-2(4H)-on (81053-88-5) → 3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydro-4H-naphtho[2,3-b]furan-2-one (6466-81-5,73069-13-3,81130-16-7)

Guidance literature:

With trichlorophosphate; In pyridine; for 5h; Ambient temperature;

Reference yield: 45.0%

9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one (94204-13-4) → 3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydro-4H-naphtho[2,3-b]furan-2-one (6466-81-5,73069-13-3,81130-16-7)

Guidance literature:

With thionyl chloride; In dichloromethane; at 30 ℃;

DOI:10.1021/ol035022f

Reference yield:

→ atractylenolide II (6466-81-5,81130-16-7,73069-13-3)

Guidance literature:

DOI:10.1248/cpb.10.641 DOI:10.1016/0040-4020(66)80093-5

upstream raw materials:

(4aα,8aβ,8α,9aβ)-4a,5,6,7,8,8a,9,9a-Octahydro-9-hydroxy-3,8a-dimethyl-5-methylennaphtho<2,3-b>furan-2(4H)-on

9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one

1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene

1,2,3,4,5,8-hexahydro-1-hydroxy-6-methoxynaphthalene

Downstream raw materials:

3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

(+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

(+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one

Refernces

• 1、 Bagal, Sharanjeet K.,Adlington, Robert M.,Baldwin, Jack E.,Marquez, Rodolfo,Cowley, Andrew. "Biomimetic synthesis of biatractylolide and biepiasterolide". . p. 3049 - 3052. Retrieved 2007/10/03.
• 2、 HIKINO,HIKINO,YOSIOKA. "Structure and autoxidation of atractylon.". . p. 641 - 642. Retrieved 2007/10/07.