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Aristolochic acid

Aristolochic acid structure

CAS No:
313-67-7
Formula:
C17H11NO7
Chemical Name:
Aristolochic acid
Synonyms:
Phenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid,8-methoxy-6-nitro-;8-Methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid;Aristolochic acid I;Tardolyt;TR 1736;Aristolochic acid;Aristolochic acid A;Aristolochic acid 1;NSC 11926;NSC 50413;Aristolochia A;8-Methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid;12770-90-0;61117-05-3;1414787-57-7
Categories:
Biochemical Engineering > Biological Response Modifiers

Description

Aristolochic acid A (Aristolochic acid I) is the main component of plant extract Aristolochic acids, which are found in various herbal plants of genus Aristolochia and Asarum. AAI significantly reduces both activator protein 1 (AP-1) and NF-κB activities. Aristolochic acid A reduces BLCAP gene expression in human cell lines[1].

Aristolochic acid is 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 is found 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 both carcinogenic and nephrotoxic. It has a role as a nephrotoxin, a carcinogenic agent, a mutagen, a toxin and a metabolite. It is a monocarboxylic acid, a C-nitro compound, a cyclic acetal, an organic heterotetracyclic compound and an aromatic ether.

Aristolochic acid Basic Attributes

Molecular Weight：

341.27

Exact Mass：

341.27

EC Number：

206-238-3

UNII：

94218WFP5T

NSC Number：

50413|11926

DSSTox ID：

DTXSID0040969

HScode：

29329990

Characteristics

PSA：

111

XLogP3：

3.6

Appearance：

yellow powder

Density：

1.6±0.1 g/cm3

Melting Point：

278 °C (decomp)

Boiling Point：

615.5°C at 760 mmHg

Flash Point：

326.0±31.5 °C

Refractive Index：

1.747

Water Solubility：

DMSO: soluble

Storage Conditions：

2-8°C

Toxicity：

Oral-rat LD50: 184 mg/kg; Oral-Mouse LD50: 55.9 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1(b)

Transport codes：

UN 1544 6.1/PG 3

wgk germany：

hazard class code：

25-68-36/37/38-23/24/25-45

safety instructions：

7-35-45-36/37/39-26-53

RTECS Number：

CF3325000

Marks：

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from food materials

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)|Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

MeSH Entry Terms：

8-methoxy-6-nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid

Aristolochic acid Use and Manufacturing

Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids

Computed Properties

Molecular Weight:341.27
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:341.05355169
Monoisotopic Mass:341.05355169
Topological Polar Surface Area:111
Heavy Atom Count:25
Complexity:550
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Aristolochic acid

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
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