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Moligand™, analytical standard Analytical standard,Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Protected from light,Store at -20°C,Argon charged Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 11 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Aristolochic Acid is an alkaloid that was originally derived from Aristolochia radix. This compound is a potent PLA2 enzyme inhibitor and also suppresses edema-inducing activity as well as direct and indirect hemolytic activity. Specifically, Aristolochic Acid displays anti-inflammatory activity against edema in mouse foot pads induced by PLA2. Other experiments have shown this agent to be associated with aristolochic acid nephropathy. Mechanistic studies have reported Aristolochic Acid to play a regulatory role towards genes in DNA repair processes and responses to DNA damage stimulus, regulation of cell cycle, and apoptosis. More detailed studies have shown this compound to up-regulate GADD 45β, NAIP genes and down-regulate TP53, PARP1, ERCC1, OGG1/2, MGMT, and ERCC2 genes. Furthermore, a down-regulation of gene expression in anti-oxidant enzymes was also observed by Aristolochic Acid treatment of human kidney tubular cells. These studies suggest that oxidative stress plays a role in the cytotoxicity of Aristolochic Acid.
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.
| Sonrisas canónicas | COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O |
|---|---|
| IUPAC Name | 8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid |
| InChIKey | BBFQZRXNYIEMAW-UHFFFAOYSA-N |
| 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) |
| Isómeros SMILES | COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O |
| WGK Alemania | 3 |
| RTECS | CF3325000 |
| CAS alternativo | 313-67-7 |
| Número NSC | 11926 |
| Términos de entrada MeSH | 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 |
| Peso molecular | 341.27 |
| Reaxy-Rn | 345159 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=345159&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Clase | Phenanthrenes and derivatives |
| Subclass | Aristolochic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aristolochic acids and derivatives |
| Alternative Parents | Naphthalenecarboxylic acids Nitronaphthalenes Benzodioxoles Anisoles Nitroaromatic compounds Alkyl aryl ethers Acetals Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Carboxylic acids Organic oxoazanium compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic oxides |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Aristolochic acid or derivatives - 1-naphthalenecarboxylic acid - 1-naphthalenecarboxylic acid or derivatives - 1-nitronaphthalene - 2-nitronaphthalene - Naphthalene - Benzodioxole - Nitroaromatic compound - Anisole - Alkyl aryl ether - Organic nitro compound - C-nitro compound - Acetal - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively. |
| External Descriptors | Isoquinoline alkaloids |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | Jan 19, 2026 | A196354 | |
| Certificate of Analysis | Nov 26, 2025 | A196354 | |
| Certificate of Analysis | Nov 26, 2025 | A196354 | |
| Certificate of Analysis | Oct 14, 2025 | A196354 | |
| Certificate of Analysis | Jun 01, 2022 | A196354 | |
| Certificate of Analysis | Jun 01, 2022 | A196354 |
| Solubilidad | Soluble in ethanol, acetone, chloroform, ether, aniline, alkalies, acetic acid, and DMSO (25 mg/ml), slightly soluble in water.practically Insoluble in benzene, and carbon disulfide. |
|---|---|
| Sensibilidad | Air sensitive;Moisture sensitive;Light sensitive;Heat sensitive |
| Punto de fusión (°C) | 278℃ |
| Peso molecular | 341.270 g/mol |
| XLogP3 | 3.600 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Exact Mass | 341.054 Da |
| Monoisotopic Mass | 341.054 Da |
| Topological Polar Surface Area | 111.000 Ų |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Complexity | 550.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Danxia Wu, Li Wang, Wei Li, Xiangyang Li. (2023) Identifying a New Target for BtOBP8: Discovery of a Small Amino Ketone Molecule Containing Benzothiazole Fragments. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:37651643] [10.1021/acs.jafc.3c02594] |
| 2. Li Wang, Maoxi Huang, Zilin Wu, Min Huang, Yunlong Yan, Baoan Song, Xiangyang Li, Qing X. Li. (2022) Methyl Eugenol Binds Recombinant Gamma-Aminobutyric Acid Receptor-Associated Protein from the Western Flower Thrips Frankliniella occidentalis. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:35385288] [10.1021/acs.jafc.1c07431] |
| 3. Xuan Yu, Yuan Gao, Ying Xu, Xian Guo, Lan Guo, Ting Tan, Fan Liu, Yiqun Wan. (2022) Study of the Contents of Analogues of Aristolochic Acid in Houttuynia cordata by Ultra-High Performance Liquid Chromatography Tandem Mass Spectrometry. Foods, 11 (3): (302). [PMID:35159454] [10.3390/foods11030302] |
| 4. Jiangfei Chen, Aijun Kong, Delia Shelton, Haojia Dong, Jiani Li, Fan Zhao, Chenglian Bai, Kaiyu Huang, Wen Mo, Shan Chen, Hui Xu, Robyn L Tanguay, Qiaoxiang Dong. (2021) Early life stage transient aristolochic acid exposure induces behavioral hyperactivity but not nephrotoxicity in larval zebrafish. AQUATIC TOXICOLOGY, [PMID:34303159] [10.1016/j.aquatox.2021.105916] |
| 5. Pei Chen, Xiaoman Li, Xuemin Yan, Minglei Tian. (2021) Solid-Phase Extraction of Aristolochic Acid I from Natural Plant Using Dual Ionic Liquid-Immobilized ZIF-67 as Sorbent. Separations, 8 (2): (22). [PMID:] [10.3390/separations8020022] |
| 6. Fenqi Ji, Rongrong Jin, Chen Luo, Chunhui Deng, Yaoming Hu, Li Wang, Rongchang Wang, Jiabin Zhang, Guoxin Song. (2019) Fast determination of aristolochic acid I (AAI) in traditional Chinese medicine soup with magnetic solid-phase extraction by high performance liquid chromatography. JOURNAL OF CHROMATOGRAPHY A, [PMID:31443967] [10.1016/j.chroma.2019.460455] |
| 7. Yibo Yan, Chuixiu Huang, Xiantao Shen. (2019) Electromembrane extraction of aristolochic acids: New insights in separation of bioactive ingredients of traditional Chinese medicines. JOURNAL OF CHROMATOGRAPHY A, [PMID:31416626] [10.1016/j.chroma.2019.460424] |
| 8. Xiaoyan Liu, Yanqiu Liu, Mengchun Cheng, Hongbin Xiao. (2015) Metabolomic Responses of Human Hepatocytes to Emodin, Aristolochic Acid, and Triptolide: Chemicals Purified from Traditional Chinese Medicines. JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 29 (11): (533-543). [PMID:26149242] [10.1002/jbt.21724] |
| 9. Xuemeng Tian, Yue Wang, Sameer Hussain, Ruquan Shen, Ying Sheng, Ruiqi Yang, Lisa D. Pfefferle, Ruixia Gao. (2024) A versatile one-stone-two-birds strategy for facile fabrication of molecularly imprinted BiOBr composites: An efficient approach for selective removal of target contaminants from water. Journal of Cleaner Production, [PMID:] [10.1016/j.jclepro.2024.142767] |
| 10. Haiman Xu, Lianxia Guo, Tingying Hao, Xiaocao Guo, Meiping Huang, Haobin Cen, Min Chen, Jiaxian Weng, Meixia Huang, Zicong Wu, Zifei Qin, Jing Yang, Baojian Wu. (2024) Nasal solitary chemosensory cells govern daily rhythm in mouse model of allergic rhinitis. JOURNAL OF ALLERGY AND CLINICAL IMMUNOLOGY, [PMID:38734385] [10.1016/j.jaci.2024.04.024] |
| 11. Rongkun Zhu, Mengting Cai, Qiuyu Liao, Xiaobin Meng, Hong Yu, Huanghui Zeng, Zhuomiao Lin, Guicui Zhang. (2026) Selective determination of vancomycin in human serum using graphene quantum dots modified with Dihydroxyl functional groups. MICROCHEMICAL JOURNAL, [PMID:] [10.1016/j.microc.2025.116790] |
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