Alternariol

Names

[ CAS No. ]:
641-38-3

[ Name ]:
Alternariol

[Synonym ]:
Alternariol
Alternariol from Alternaria sp.
3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
6H-Dibenzo[b,d]pyran-6-one, 3,7,9-trihydroxy-1-methyl-
AOH
3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one

Biological Activity

[Description]:

Alternariol is a mycotoxin produced by Alternaria species. AOH inhibits the catalytic activity of topoisomerase I and topoisomerase II enzymes[1]. Alternariol exhibits a variety of therapeutic and biological properties such as phytotoxicity, cytotoxicity, anti-HIV, anti-cancer, and anti-microbial properties[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Research Areas >> Infection

[References]

[1]. Fliszár-Nyúl E, et al. Interaction of Mycotoxin Alternariol with Serum Albumin. Int J Mol Sci. 2019 May 12;20(9). pii: E2352.

[2]. Grover S, et al. The Alternaria alternate Mycotoxin Alternariol Suppresses Lipopolysaccharide-Induced Inflammation. Int J Mol Sci. 2017 Jul 20;18(7). pii: E1577.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
586.9±39.0 °C at 760 mmHg

[ Melting Point ]:
350°C (rough estimate)

[ Molecular Formula ]:
C₁₄H₁₀O₅

[ Molecular Weight ]:
258.226

[ Flash Point ]:
232.3±20.6 °C

[ Exact Mass ]:
258.052826

[ PSA ]:
90.90000

[ LogP ]:
2.93

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.731

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HP8757000

CHEMICAL NAME :: 6H-Dibenzo(b,d)pyran-6-one, 1-methyl-3,7,9-trihydroxy-

CAS REGISTRY NUMBER :: 641-38-3

BEILSTEIN REFERENCE NO. :: 0244839

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C14-H10-O5

MOLECULAR WEIGHT :: 258.24

WISWESSER LINE NOTATION :: T B666 HOVJ C1 EQ KQ MQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 4,87,1973 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 9-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 4,87,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 13-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 4,87,1973

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H310-H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28

[ Safety Phrases ]:
28-36/37/39-45

[ RIDADR ]:
UN 3462 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
HP8757000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2914400090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914400090

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Autophagy and senescence, stress responses induced by the DNA-damaging mycotoxin alternariol.

Toxicology 326 , 119-29, (2014)

The mycotoxin alternariol (AOH), a frequent contaminant in fruit and grain, is known to induce cellular stress responses such as reactive oxygen production, DNA damage and cell cycle arrest. Cellular ...

AFLP variability, toxin production, and pathogenicity of Alternaria species from Argentinean tomato fruits and puree.

Int. J. Food Microbiol. 145(2-3) , 414-9, (2011)

Large amounts of tomato fruits and derived products are produced in Argentina and may be contaminated by Alternaria toxins. Limited information is available on the genetic variability, toxigenicity, a...

Minor contribution of alternariol, alternariol monomethyl ether and tenuazonic acid to the genotoxic properties of extracts from Alternaria alternata infested rice.

Toxicol. Lett. 214(1) , 46-52, (2012)

Alternaria spp. are known to form a spectrum of secondary metabolites with alternariol (AOH), alternariol monomethyl ether (AME), altenuene (ALT) and tenuazonic acid (TA) as the major mycotoxins with ...