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Fusarium toxin

HCID 5375083
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
17924-92-4
표준 SMILES
CC1CCCC(=O)CCC/C=C/c2cc(O)cc(O)c2C(=O)O1
InChIKey
MBMQEIFVQACCCH-CLTKARDFSA-N
분자식
C18H22O5
평균 분자량
318.4 g/mol
단동위원소 질량
318.1467238

개요

(S,E)-Zearalenone is a macrolide and a member of resorcinols.

이름 및 식별자

우선 이름
Fusarium toxin
IUPAC
(12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
영어명
(E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
분자량
0

이름 및 동의어

7645-23-0RefChem:1085627Fusarium toxin(S,E)-Zearalenone(12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dioneMycotoxin F-2Toxin, fusarium(E)-3,4,5,6,7,8,9,10-Octahydro-14,16-dihydroxy-3-methyl-7-oxo-1H-2-benzoxacyclotetradecin-1-oneSCHEMBL588841orb12202956-(10-Hydroxy-6-oxo-trans-1-undecenyl)-.beta.-resorcylic acid lactoneCHEMBL1397216
이름 더 보기
(E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
CHEBI:125462CHEBI:175078MBMQEIFVQACCCH-XVNBXDOJSA-N(11S)-11-methyl-15,17-bis(oxidanyl)-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraene-7,13-dione(S,E)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dioneNCGC00095344-01NCGC00095344-03AB01209588-01

데이터베이스 식별자

CAS
17924-92-4、7645-23-0
PubChem CID
5375083
ChEMBL
CHEMBL1397216
ChEBI
CHEBI:175078
Nikkaji
J108.495J

물성

구조 계산 물성

XLogP
3.6
극성 표면적
83.8 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
5
회전 가능 결합 수
0
무거운 원자 수
23
형식 전하
0
복잡도
445

실험 및 물리화학적 성질

Melting Point164 - 165 °C
Physical DescriptionSolid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Health Effects · 1건

Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. In humans it can cause earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia, and breast cancer in women. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. (L1947, A2960)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1건

Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2960, A3014)

Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
Toxicity DataLD50: >2000 mg/kg (Oral, Mouse) (L1912) LD50: >500 mg/kg (Intraperitoneal, Mouse) (L1912)

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Zearalenone is rapidly absorbed after oral administration. In humans, most of the zearalenone absorbed is not metabolized. The main metabolites include alpha- and beta-zeralenol, and the glucuronide conjugates of both the parent compound and its metabolites. Zearalenone and its metabolites are excreted mainly in the bile. (A741, L1912)

Cellular LocationsMembrane

용도 및 제조

Uses · 1건

Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. (L1947)

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