MilliporeSigma
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A5512

Sigma-Aldrich

Aristolochic acid I

powder

Synonym(s):
TR 1736
Empirical Formula (Hill Notation):
C17H11NO7
CAS Number:
Molecular Weight:
341.27
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥90% (HPLC)

form

powder

color

yellow

mp

269-270 °C

solubility

DMSO: soluble
ethanol: soluble

storage temp.

2-8°C

SMILES string

COc1cccc2c1cc([N+]([O-])=O)c3c(cc4OCOc4c23)C(O)=O

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)

InChI key

BBFQZRXNYIEMAW-UHFFFAOYSA-N

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General description

Aristolochic acid is a naturally occurring plant metabolite found in Aristolochia sp, Bragantia sp. or Asarum sp. plants.[1] It comprises a mixture of nitrophenanthrene carboxylic acids such as aristolochic acid I and II.[2]

Application

Aristolochic acid I have been used:

  • as a standard for the analysis of Aristolochia sprucei crude extract by high-performance liquid chromatography[3]
  • to study its effects on histone deacetylase 3 (HDAC3) aberration and renal fibrosis[4]
  • to induce acute aristolochic acid nephropathy and to study its impact on miRNA and mRNA expression in mice[5]

Packaging

25 mg in poly bottle
100 mg in glass bottle

Biochem/physiol Actions

Aristolochic acid is a potent inhibitor of phospholipase A2 (PLA2), hyaluronidase, and acetylcholinesterase plasma proteases from snake venoms.[6] Aristolochic acid is considered a herbal medicine and shows therapeutic effects against obstetrics, snake bites, gout, and rheumatism.[2] It exhibits anti-inflammatory and anti-malarial properties.[7] In addition, it is also considered a genotoxic mutagen[2] and causes aristolochic acid nephropathy (AAN), characterized by interstitial fibrosis and urothelial cancer.[2]
Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1A - Muta. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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