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SMB00336

Sigma-Aldrich

Aristolochic acid B

≥97% (HPLC)

Synonym(s):

6-Nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid, Aristolochic acid II, Noraristolochic acid

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About This Item

Empirical Formula (Hill Notation):
C16H9NO6
CAS Number:
475-80-9
Molecular Weight:
311.25
MDL number:
MFCD01708574
UNSPSC Code:
12352200
PubChem Substance ID:
329824960
NACRES:
NA.25

Assay

≥97% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

OC(C1=C2C([N+]([O-])=O)=CC3=CC=CC=C3C2=C4OCOC4=C1)=O

InChI

1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)

InChI key

MEEXETVZNQYRSP-UHFFFAOYSA-N

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General description

Aristolochic acid B or Aristolochic acid II (AA-II) is one of the most abundant secondary metabolites produced in leaves, roots, and stems of Aristolochiaceae family plants. AA-II is structurally similar to Aristolochic acid I (AA-I) with the only difference being the methoxy group at C8.

Application

Aristolochic acid B may have been used to test its fungi-toxic effect on Botrytis cinerea. It may also have been used as a reference standard to study its effects on in vivo metabolism using high-performance liquid chromatography/electrospray ionization mass spectrometry (HPLC/ESI-MS).

Biochem/physiol Actions

Aristolochic acid B inhibits in vitro phospholipid hydrolysis by HSF-PLA2 in a dose-dependent manner.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 2 Inhalation - Muta. 2

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alena Dedı Ková et al.
Chemical research in toxicology, 33(11), 2804-2818 (2020-09-08)
The plant extract aristolochic acid (AA), containing aristolochic acid I (AAI) and II (AAII) as major components, causes aristolochic acid nephropathy and Balkan endemic nephropathy, unique renal diseases associated with upper urothelial cancer. Differences in the metabolic activation and detoxification
R Melo et al.
Letters in applied microbiology, 68(1), 48-55 (2018-10-17)
The fungitoxic effect of aristolochic acids I and II on mycelial growth and conidial germination of Botrytis cinerea was analysed. Aristolochic acid I had a higher effect on mycelial growth of B. cinerea than aristolochic acid II with IC50 value
Sivaprasad Attaluri et al.
Nucleic acids research, 38(1), 339-352 (2009-10-27)
Aristolochic acids I and II (AA-I, AA-II) are found in all Aristolochia species. Ingestion of these acids either in the form of herbal remedies or as contaminated wheat flour causes a dose-dependent chronic kidney failure characterized by renal tubulointerstitial fibrosis.

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