Aristolochic acid CAS 313-67-7
Introduction：Basic information about Aristolochic acid CAS 313-67-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Aristolochic acid Basic information
| Product Name: | Aristolochic acid |
| Synonyms: | Aristolochic acid Ⅰ;nsc-50413;tardolyt;8-METHOXY-6-NITROPHENANTHROL(3,4-D)-1,3-DIOXIDE-5-CARBOXYLIC ACID;ARISTOLOCHIC ACID;ARISTOLOCHIC ACID A;ARISTOLOCHIC ACID I;Aristolochic acid, mixture of I and II, 96% |
| CAS: | 313-67-7 |
| MF: | C17H11NO7 |
| MW: | 341.27 |
| EINECS: | 206-238-3 |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract |
| Mol File: | 313-67-7.mol |
Aristolochic acid Chemical Properties
| Melting point | 260 °C |
| Boiling point | 476.92°C (rough estimate) |
| density | 1.3162 (rough estimate) |
| refractive index | 1.4500 (estimate) |
| storage temp. | 2-8°C |
| solubility | DMSO: soluble |
| pka | 2.99±0.20(Predicted) |
| form | powder |
| color | yellow |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20) |
| InChIKey | LIDQMWRBMLSXLL-UHFFFAOYSA-N |
| SMILES | O1C2=C3C(=C(C(O)=O)C=C2OC1)C([N+]([O-])=O)=CC1C3=CC=CC=1OC |
| CAS DataBase Reference | 313-67-7(CAS DataBase Reference) |
| IARC | 1 (Vol. 82, 100A) 2012, 1 (Vol. 82, 100A) 2012 |
Safety Information
| Hazard Codes | T |
| Risk Statements | 25-68-36/37/38-23/24/25-45 |
| Safety Statements | 7-35-45-36/37/39-26-53 |
| RIDADR | UN 1544 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | CF3325000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29329990 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Carc. 1A Muta. 1B |
| Toxicity | LD50 in male, female mice, male, female rats (mg/kg): 38.4, 70.1, 82.5, 74.0 i.v.; 55.9, 106.1, 203.4, 183.9 orally (Mengs) |
| 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. |
| Chemical Properties | Shiny brown leaflets or a yellow or whitepowder. |
| 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). |
| History | At a clinic in Brussels, Belgium, a group of women who had all taken the same weight loss supplement, Aristolochia fangchi, which contained aristolochic acid, was first diagnosed with aristolochic acid poisoning. Balkan endemic nephropathy (BEN) was later found to be also the result of aristolochic acid (AA) consumption. Balkan endemic nephropathy is likely caused by low-level AA exposure, possibly from the contamination of wheat flour seeds by Aristolochia clematitis. BEN falls under the umbrella of what is now known as aristolochic acid nephropathy, the prevalent symptom of AA poisoning . |
| 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. |
| Uses | PLA2 inhibitor |
| Uses | Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids |
| Definition | ChEBI: A monocarboxylic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and isfound in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is bth carcinogenic and nephrotoxic. |
| Indications | Due to the widely associated kidney problems and urothelial cancers, the FDA has issued warnings regarding consumption of AA-containing supplements. |
| Brand name | Acidum aristolchicum;Descresepet;Fago-araxin;Fluocinova;Predno-facilus haemota. |
| World Health Organization (WHO) | Extracts of aristolochiaceae have traditionally been used as abitter for which a broad range of therapeutic effects has been claimed. Aristolochicacid is claimed to promote phagocytosis and to have immunostimulant activity.However, in 1981, a three-month toxicity study in rats revealed the carcinogenicpotential of aristolochic acid and preparations containing this substance havesince been withdrawn in several countries. |
| General Description | This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG |
| Biochem/physiol Actions | Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model. |
| Pharmacology | In 1992, some cases of women present with a rapidly progressive renal failure after having a slimming regimen including powdered extracts of Chinese herbal preparations. This outbreak of renal failure eventually resulted in about 100 cases in 1998, 70% of them being in end-stage renal disease (ESRD) . Recent research has confirmed that the main reason leading to renal injury is aristolochic acid found in many Chinese herbs . Aristolochic acid, a potent human carcinogen fromAristolochia plants, is associated with the incidence of urothelial carcinoma in theupper urinary tract (UUC). After the metabolic activation, aristolochic acid reactedwith DNA to form aristolactam (AL)-DNA adducts. Mainly pathological changesare in renal cortex, where they serve as a specific biomarker, and are also found inurothelium, where they lead to a unique mutational signature in the TP53 tumorsuppressor gene. The conclusion is that exposure to aristolochic acid gives rise tothe incidence of UUC, a finding with significant implications for the global publichealth . |
| Clinical Use | Aristolochia species are nephrotoxic and carcinogenic, and FDA has issued warnings regarding consumption of AA-containing supplements. |
| Safety Profile | Confirmed carcinogen.Poison by ingestion, intraperitoneal, andintravenous routes. Mutation data reported.When heated to decomposition it emitstoxic fumes of NO,.Potentially Toxic Chemicals: April 1982."Vol. 5 No. 1: The Ministry of Health of theFederal Republic of Germany haswithdrawn from the national market drugscontaining aristolochic acid. The decisionresulted from the demonstration of acarcinogenic potential in a three-monthingestion toxicity study undertaken in rats.Aristolochic acid is claimed to promotephagocytosis and to have immunostimulantactivity. A growth-inhibiting effect onexperimentally induced tumors has beendescribed, but this effect has not beenshown to have any clinical relevance.Extracts of species of Aristolochiacea havetradtionally been used as a bitter, and abroad range of therapeutic effects has beenclaimed. |
| Potential Exposure | Aristolochic acids are alkaloids usedprimarily as a chemical intermediate for pharmaceuticals,lab chemicals, herbal extract, drug. |
| Shipping | UN1544 Alkaloids, solid, n.o.s. or Alkaloid salts,solid, n.o.s. poisonous, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. PG III. |
| Incompatibilities | Compounds of the carboxyl group reactwith all bases, both inorganic and organic (i.e., amines)releasing substantial heat, water and a salt that may beharmful. Incompatible with oxidizers (chlorates, nitrates,peroxides, permanganates, perchlorates, chlorine, bromine,fluorine, etc.); contact may cause fires or explosions. Keepaway from alkaline materials, strong bases, strong acids,oxoacids, epoxides. |
| Waste Disposal | It is inappropriate and possiblydangerous to the environment to dispose of expired orwaste drugs and pharmaceuticals by flushing them downthe toilet or discarding them to the trash. Household quantitiesof expired or waste pharmaceuticals may be mixedwith wet cat litter or coffee grounds, double-bagged inplastic, discard in trash. Larger quantities shall carefullytake into consideration applicable DEA, EPA, and FDAregulations. If possible return the pharmaceutical to themanufacturer for proper disposal being careful to properlylabel and securely package the material. Alternatively, thewaste pharmaceutical shall be labeled, securely packagedand transported by a state licensed medical waste contractorto dispose by burial in a licensed hazardous or toxic wastelandfill or incinerator. All federal, state, and local environmentalregulations must be observed. |
Aristolochic acid Preparation Products And Raw materials
