2198-93-8

Usage

Chemical class

Trichothecene mycotoxin

Producing organisms

Various species of fungi within the Fusarium genus

Notoriety

Known for its potent toxicity and ability to cause adverse health effects in humans and animals

Exposure routes

Ingestion of contaminated food or inhalation of airborne particles

Toxic effects

Disruption of protein synthesis, induction of oxidative stress, and suppression of the immune system

Hazardous substance

Considered a hazardous substance due to its toxic nature

Regulation

Regulated to protect public health

Chemical structure

Contains a 12,13-epoxide group and a 9-en-4β-ol functional group

Molecular weight

Approximately 292.37 g/mol (calculated from the molecular formula)

Physical state

Likely a solid at room temperature (not provided in the material, but a common state for mycotoxins)

Solubility

Soluble in organic solvents such as methanol, ethanol, and acetonitrile (not provided in the material, but a common solubility profile for mycotoxins)

Detection methods

Analytical techniques such as gas chromatography-mass spectrometry (GC-MS) or liquid chromatography-mass spectrometry (LC-MS) can be used to detect and quantify 12,13-Epoxytrichothec-9-en-4β-ol in samples (not provided in the material, but common methods for detecting mycotoxins)

Occurrence

Can be found in contaminated crops, such as wheat, barley, and oats, as well as in the indoor environment due to mold growth (not provided in the material, but a common occurrence for mycotoxins)

InChI:InChI=1/C15H22O3/c1-9-4-5-13(2)11(6-9)18-12-7-10(16)14(13,3)15(12)8-17-15/h6,10-12,16H,4-5,7-8H2,1-3H3/t10-,11-,12-,13+,14?,15?/m1/s1

Upstream product

• 75323-72-7 trichodermadiene 
• 75323-72-7 trichodermadiene 
• 76740-74-4 trichodermadienediol A 
• 76685-81-9 trichodermadienediol B 
• 156250-74-7 harzianum B 
• 2270-40-8 anguidine 
• 2198-94-9 diacetyl verrucarol 
• 4682-50-2 C₁₇H₂₄O₄ 
• 118714-91-3 4-(dimethylfluorosilyl)-12-oxonortrichothec-9-ene 
• 118714-90-2 4-(dimethylfluorosilyl)-12-hydroxynortrichothec-9-ene 
• 74501-20-5 Benzoic acid (1S,2R,7R,9R,11R)-5-hydroxy-1,2,5-trimethyl-12-oxo-8-oxa-tricyclo[7.2.1.0^2,7]dodec-11-yl ester 
• 74501-19-2 Benzoic acid (1R,2R,7R,9R,11R,12R)-5,12-dihydroxy-1,2,5-trimethyl-8-oxa-tricyclo[7.2.1.0^2,7]dodec-11-yl ester 
• 74501-17-0 (1R,2S,7S,9S,11S,12S)-11,12-Dihydroxy-1,2-dimethyl-8-oxa-tricyclo[7.2.1.0^2,7]dodecan-5-one 
• 74501-18-1 (1R,2S,7S,9S,11S,12S)-1,2,5-Trimethyl-8-oxa-tricyclo[7.2.1.0^2,7]dodecane-5,11,12-triol 

Downstream Products

• 1245791-09-6 C₂₂H₂₅ClO₄ 
• 22263-48-5 C₂₂H₂₆O₄ 
• 1245791-11-0 C₂₃H₂₈O₄ 
• 1245791-13-2 C₂₂H₂₅ClO₄ 
• 1245791-08-5 C₂₃H₂₈O₄ 
• 1245791-10-9 C₂₃H₂₈O₅ 
• 1431698-53-1 (4β)-12,13-epoxytrichothec-9-en-4-yl (2E)-3-phenylprop-2-enoate 
• 1431698-52-0 (4β)-12,13-epoxytrichothec-9-en-4-yl (2,4,6-trimethylphenyl)acetate 
• 1431698-51-9 (4β)-12,13-epoxytrichothec-9-en-4-yl 2-phenylacetate 
• 1431698-62-2 (4β,8β)-4-(acetyloxy)-12,13-epoxytrichothec-9-en-8-yl (2E)-3-phenylprop-2-enoate 
• 1431698-61-1 (4β,8β)-4-(acetyloxy)-12,13-epoxytrichothec-9-en-8-yl 4-fluorobenzoate 
• 1245791-12-1 C₂₂H₂₅FO₄ 
• 2077-58-9 C₁₅H₂₀O₃ 

Relevant academic research and scientific papers

Trichodermates A-F, New Cytotoxic Trichothecenes from the Plant Pathogenic Fungus Trichoderma sp.

Trichodermates A - F (1-6, resp.), six new trichothecene polyunsaturated octadioic acid esters, and (-)-harzianum B (7) were isolated from the fermentation extract of Trichoderma sp., a plant pathogenic fungus isolated from stem rot of an unidentified tree in Thailand. The structures of 1-7 were elucidated by NMR experiments. The absolute configuration at C(12) in 3 was assigned by in situ dimolybdenum circular dichroism method, whereas that in 7 was deduced after hydrolysis of 7 to 8 via modified Mosher's method. Compounds 1 and 2 showed modest cytotoxic activities against the K562 (human myelogenous leukemia) cell line with IC50 values of 12.12 and 13.08 μM, respectively.

TRICHODERMADIENE: A NEW TRICHOTHECENE

A new trichothecene, trichodermadiene (3), possessing a dienic ester side chain has been isolated and characterized.

Synthesis of trichodermin derivatives and their antimicrobial and cytotoxic activities

Trichothecene mycotoxins are recognized as highly bioactive compounds that can be used in the design of new useful bioactive molecules. In Trichoderma brevicompactum, the first specific step in trichothecene biosynthesis is carried out by a terpene cyclas

Synthesis and antifungal activities of trichodermin derivatives as fungicides on rice

Twenty new trichodermin derivatives, 2a-5, containing alkoxy, acyloxy, and Br groups in 4-, 8-, 9-, 10- and 16-positions were synthesized and characterized. The antifungal activities of the new compounds against rice false smut (Ustilaginoidea virens), ri

Synthesis and antifungal activity of trichodermin derivatives

A series of derivatives were synthesized from trichodermin (1) which was an antifungal metabolite produced by Trichoderma taxi sp. nov. Their structures were confirmed by 1H NMR, MS spectrum. Their antifungal activities were evaluated in vitro. The preliminary structure activity relationships (SAR) results indicated that the double bond, epoxide moiety and ester group were main pharmacophore elements, the stereochemistry of C4 position played a key role as well, and the compounds 1e-1g displayed stronger antifungal activity against Magnaporthe grisea than 1.

Isolation and Characterization of the Trichoverroids and New Roridins and Verrucarins

Myrothecium verrucaria grown on a large scale (760 L) has yielded a variety of new trichothecenes including the nonmacrocyclic trichoverroids 13-19, which contain a pendant C4 cis,trans-dienic ester side chain normally common only to the macrocyclic roridins and verrucarins.Several novel macrocyclic trichothecenes (roridins J and K acetate) and verrucarins L and L acetate also were isolated and characterized.

The ready conversion of anguidine into verrucarol and trichodermol

Anguidine, 1, is readily converted into verrucarol diacetate, 2d, in 85 percent yield by application of the Barton-McCombie deoxygenation procedure. To enable conversion into trichodermol, 3a, the primary hydroxyl group of verrucarol, 2a, is selectively acetylated or is selectively acetylated or preferably silylated, thereby paving the way for its deoxygenation in three simple, high-yield reactions.