Aristolochic acid

Base Information

• Chemical Name: Aristolochic acid
• CAS No.: 313-67-7
• Deprecated CAS: 61117-05-3,12770-90-0,1414787-57-7
• Molecular Formula: C17H11NO7
• Molecular Weight: 341.277
• Hs Code.: 29329990
• European Community (EC) Number: 206-238-3
• NSC Number: 50413,11926
• UNII: 94218WFP5T
• DSSTox Substance ID: DTXSID0040969
• Nikkaji Number: J20.596F
• Wikipedia: Aristolochic_acid
• Wikidata: Q21099362
• Metabolomics Workbench ID: 52975
• ChEMBL ID: CHEMBL93353
• Mol file: 313-67-7.mol

Synonyms:8-methoxy-6-nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid;aristolochic acid;aristolochic acid A;aristolochic acid I;aristolochic acid I, sodium salt;sodium aristolochate;Tardolyt

Chemical Property of Aristolochic acid

Chemical Property:

• Appearance/Colour: Shiny brown leaflets
• Vapor Pressure: 5.24E-16mmHg at 25°C
• Melting Point: 260 °C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 615.5 °C at 760 mmHg
• PKA: 2.99±0.20(Predicted)
• Flash Point: 326 °C
• PSA: 110.81000
• Density: 1.571 g/cm³
• LogP: 3.85990
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 341.05355169
• Heavy Atom Count: 25
• Complexity: 550

Purity/Quality:

AristolochicAcidA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-68-36/37/38-23/24/25-45
• Safety Statements: 7-35-45-36/37/39-26-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O
• Description: Aristolochic acid first appeared in Chinese medicine in the fifth century AD, while it was used to treat kidney and urinary diseases, as well as gout, snakebites, and a variety of other ailments. In many of these cases, aristolochic acid was just one of the main components of the salves. In the first century, aristolochic acid was first described as a composition of ingested medicine to treat symptoms such as asthma, hiccups, pains, and spasms.
• Physical properties: Appearance: brown sheet crystal or yellow powder. Solubility: practically insoluble in water and soluble in ethanol, chloroform, ethyl ether, acetone, glacial acetic acid, and aniline. Melting point: 260–265?°C (500–509?°F; 533–538?K).
• Uses: Aristolochic acid I is a potent phospholipase A2 inhibitor. Aristolochic acid I induces tumor formation in rat kidneys and apoptosis in human renal proximal tubular epithelial cells. PLA2 inhibitor Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids
• Indications: Due to the widely associated kidney problems and urothelial cancers, the FDA has issued warnings regarding consumption of AA-containing supplements.
• Clinical Use: Aristolochia species are nephrotoxic and carcinogenic, and FDA has issued warnings regarding consumption of AA-containing supplements.

Technology Process of Aristolochic acid

There total 2 articles about Aristolochic 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:

C17H11NO6 → aristolochic acid I (313-67-7,61117-05-3)

Guidance literature:

With sodium chlorite; In aq. phosphate buffer; dimethyl sulfoxide;

DOI:10.1021/tx500122x

Reference yield:

→ aristolochic acid I (313-67-7,61117-05-3)

Guidance literature:

DOI:10.1139/v69-070

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + aristolochic acid I (313-67-7,61117-05-3) → aristolochic acid I methyl ester (1169-60-4)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0031-9422(00)97687-8

Downstream raw materials:

9-Nitro-1-methoxy-5,6-methylendioxy-phenanthren

aristolochic acid I methyl ester

aristololactam I

aristolic acid

Refernces

• 1、 -. "Method of inhibiting secretory effects caused by Cholera". . . Retrieved 2008/06/13.