Gliotoxin
Suppliers
Names
[ CAS No. ]:
67-99-2
[ Name ]:
Gliotoxin
[Synonym ]:
(1R,7S,8S,11R)-7-Hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0.0]pentadeca-3,5-diene-10,14-dione
epithiodiketopiperazine
Gliotoxin,(3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
MFCD00058534
(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
[3R-(3a,5ab,6b,10aa)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
10H-3,10a-(Iminomethano)[1,2,4]dithiazino[4,3-a]indole-4,11(3H)-dione, 5a,6-dihydro-6-hydroxy-3-(hydroxymethyl)-12-methyl-, (3R,5aS,6S,10aR)-
Gliotoxin
Chemical & Physical Properties
[ Density]:
1.8±0.1 g/cm3
[ Boiling Point ]:
699.7±55.0 °C at 760 mmHg
[ Melting Point ]:
153.5ºC
[ Molecular Formula ]:
C13H14N2O4S2
[ Molecular Weight ]:
326.391
[ Flash Point ]:
377.0±31.5 °C
[ Exact Mass ]:
326.039490
[ PSA ]:
131.68000
[ LogP ]:
0.52
[ Vapour Pressure ]:
0.0±5.0 mmHg at 25°C
[ Index of Refraction ]:
1.814
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- KB4725000
- CHEMICAL NAME :
- 10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-hydroxy-3- (hydroxymethyl)-2-methyl-, (3R-(3-alpha,5a-beta,6-beta,10a-alpha))-
- CAS REGISTRY NUMBER :
- 67-99-2
- BEILSTEIN REFERENCE NO. :
- 0050675
- LAST UPDATED :
- 199709
- DATA ITEMS CITED :
- 9
- MOLECULAR FORMULA :
- C13-H14-N2-O4-S2
- MOLECULAR WEIGHT :
- 326.41
- WISWESSER LINE NOTATION :
- T C6 B566/JO A 2BJ O AVN JXSS NNV EU GU MHTT&&J DQ M1Q N
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 45 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 50 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 67 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 32 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 25 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 7800 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 45 mg/kg
- TOXIC EFFECTS :
- Vascular - BP lowering not characterized in autonomic section Gastrointestinal - hypermotility, diarrhea
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - hamster
- DOSE/DURATION :
- 25 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
MUTATION DATA
- TYPE OF TEST :
- DNA repair
- TEST SYSTEM :
- Bacteria - Bacillus subtilis
- DOSE/DURATION :
- 250 mg/L
- REFERENCE :
- MYCPAH Mycopathologia. (Kluwer Academic Pub. Group, Distribution Centre, POB 322, 3300 AH Dordrecht, Netherlands) V.1- 1938- Volume(issue)/page/year: 87,43,1984
Safety Information
[ Symbol ]:
GHS02, GHS07
[ Signal Word ]:
Danger
[ Hazard Statements ]:
H225-H302-H312-H319-H332
[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338
[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
[ Hazard Codes ]:
T
[ Risk Phrases ]:
25
[ Safety Phrases ]:
S45;S36/S37/S39
[ RIDADR ]:
UN 3462 6.1/PG 3
[ WGK Germany ]:
3
[ RTECS ]:
KB4725000
[ Packaging Group ]:
III
[ Hazard Class ]:
6.1(b)
[ HS Code ]:
29419090
Synthetic Route
Precursor & DownStream
Precursor
DownStream
Articles
Mol. Microbiol. 82(1) , 39-53, (2011)
The saprophytic fungus Aspergillus fumigatus is the most important air-borne fungal pathogen. The cell wall of A. fumigatus has been studied intensively as a potential target for development of effect...
Anal. Bioanal. Chem 401(8) , 2519-29, (2011)
Gliotoxin is produced by non-ribosomal peptide synthesis and secreted from certain fungi, including Aspergillus fumigatus. It is an epipolythiodioxopiperazine that contains an intact disulphide bridge...
Toxicol. In Vitro 27(6) , 1970-8, (2013)
The mycotoxins patulin, gliotoxin and sterigmatocystin can be produced by common indoor moulds and enter the human body via inhalation of mycotoxin containing spores and particulates. There are variou...