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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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLCF7305
SLBM4878V

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Aristolochic acid I phyproof® Reference Substance

PHL89565

Aristolochic acid I

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
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.
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

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