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Aflatoxin M1

HCID 178785926
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Grundinformationen

CAS
1330042-13-1
Standard-SMILES
COc1cc2c(c3oc(=O)c4c(c13)CCC4=O)[C@]1(O)C=CO[C@@H]1O2
InChIKey
MJBWDEQAUQTVKK-IAGOWNOFSA-N
Summenformel
C17H12O7
Durchschnittliche Molmasse
328,27 g/mol

Überblick

Aflatoxin M1 is a member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group. It has a role as a mammalian metabolite, an Aspergillus metabolite and a human xenobiotic metabolite. It is an aflatoxin, a tertiary alcohol, an aromatic ether and an aromatic ketone. It is functionally related to an aflatoxin B1.

Namen und Bezeichner

Bevorzugter Name
Aflatoxin M1
IUPAC
(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
Englischer Name
Aflatoxin M1-d3
Summenformel
C17H12O7
Molmasse
328.27298

Namen und Synonyme

AFLATOXIN M16795-23-94-Hydroxyaflatoxin B1AFM1Aflatoxin MCHEBI:78576DTXSID40891797I3020O28I3(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dioneAflatoxin M(1)4 Hydroxyaflatoxin B1Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-1,11-dione, 2,3,6a,9a-tetrahydro-9a-hydroxy-4-methoxy-, (6aR-cis)-
Weitere Namen anzeigen
AFM1-d3Aflatoxin M1-d36aR,9aR)-2,3,6a,9a-Tetrahydro-9a-hydroxy-4-(Methoxy-d3)-cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione
(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo(10.7.0.0^(2,9).0^(3,7).0^(13,17))nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dioneRefChem:110037DTXCID001031034229-865-43-hydroxy-11-methoxy-6,8,19-trioxapentacyclo(10.7.0.02,9.03,7.013,17)nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione25325-49-9

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,5
Polarare Oberfläche (TPSA)
91,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
1
Schwere Atome
24
Formalladung
0
Komplexität
695

Experimentelle und physikochemische Eigenschaften

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point299 °C
Physical DescriptionSolid
Collision Cross Section · 2 Einträge

177.8 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine]

173.78 Ų [M-H]-

Sicherheit und Regulatorisches

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GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300+H310+H330 (20%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesAcute Tox. 1 (100%)

Toxikologische Informationen

Treatment · 1 Eintrag

Administration of phonobarbital enhances hepatic transformation activities and also protects against AFB-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. (A704, L1879)

Health Effects · 1 Eintrag

The main target organ in mammals is the liver so aflatoxicosis is primarily a hepatic disease. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Moreover, protracted exposure to aflatoxins has been associated with hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Thus, it is not clear in these various instances whether aflatoxin is a primary cause of the disease, is an innocent bystander which accumulates secondary to the disease process, or is a contributing cause in conjunction with other factors. It is also mutagenic and teratogenic. Inhaled aflatoxins may produce pulmonary adenomatosis. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. (A704, L1956)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Aflatoxin M1 is a known human metabolite of aflatoxin b1.

Aflatoxin M1 is P450 activated to its epoxide and detoxified by glutathione S transferase. [Pubchem] (A2972)

MeSH Pharmacological Classification · 1 Eintrag

Substances which, when ingested, inhaled, or absorbed, or when applied to, injected into, or developed within the body in relatively small amounts may, by their chemical action, cause damage to structure or disturbance of function. (From Dorland, 27th ed)

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 1 Eintrag

The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Crops which are frequently affected include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). The toxin can also be found in the milk of animals which are fed contaminated feed. Thus, aflatoxins are usually encountered in thecontext of chronic exposure, via food intake or secondary to the handling of foodstuffs. (L1956)

Use ClassificationFood Contaminant -> MYCOTOXIN -> JECFA Functional Classes

Anwendungen

VerwendenLabelled Aflatoxin M1 (A357500). An Aspergillus flavus metabolite. Aflatoxin M1 in milk as a secondary metabolite of the Aflatoxin B1 formed in moldy forages. It is cancerogenic, hepatotoxic, and imm unosuppressive in animals and man.

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Datenbank-Bezeichner

CAS
1330042-13-1
ChEBI
CHEBI:78576
UNII
I3020O28I3
EC Number
229-865-4
Nikkaji
J5.140C
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 Eintrag

Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin M1 is P450 activated to its epoxide. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. (L1877, A2859, A2972)

Signs and SymptomsA broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. (L1879)
Carcinogen Classification2B, possibly carcinogenic to humans. (L135)