Aflatoxicol
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| Category | Mycotoxins |
| Catalog number | BBF-04527 |
| CAS | 29611-03-8 |
| Molecular Weight | 314.29 |
| Molecular Formula | C17H14O6 |
| Purity | ≥98% |
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Description
The 2 ppm acetonitrile solution of aflatoxicol, a metabolite of aflatoxin, could be commonly used as a standard solution.
Specification
| Synonyms | Aflatoxin Ro; (1S-(1alpha,6abeta,9abeta))-2,3,6a,9a-Tetrahydro-1-hydroxy-4-methoxycyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-11(1H)-one; Cyclopenta(c)furo(3',2':4,5)furo(2,3-h)(1)benzopyran-11(1H)-one, 2,3,6a,9a-tetrahydro-1-hydroxy-4-methoxy-, (1S,6aR,9aS)-; AFL |
| Storage | Store at 2-8°C |
| IUPAC Name | (3S,7R,16S)-16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one |
| Canonical SMILES | COC1=C2C3=C(C(CC3)O)C(=O)OC2=C4C5C=COC5OC4=C1 |
| InChI | InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3/t8-,9-,17+/m0/s1 |
| InChI Key | WYIWLDSPNDMZIT-IRWWLHRVSA-N |
| Source | 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. |
Properties
| Appearance | White Powder |
| Application | Only to be used as a reference standard in analytical laboratories. |
| Boiling Point | 552.1°C at 760 mmHg |
| Melting Point | 268-269°C |
| Density | 1.56 g/cm3 |
| Solubility | Soluble in Methanol, Ethanol, DMSO, Ethyl Acetate; Insoluble in Water |
Toxicity
| Carcinogenicity | Not directly listed by IARC. Aflatoxin B1 is carcinogenic to humans (Group 1). |
| Mechanism Of Toxicity | 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 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. |
Reference Reading
1. Reduction of aflatoxin B1 to aflatoxicol: a comprehensive DFT study provides clues to its toxicity
Jerzy Leszczynski, Guvanchmyrat Paytakov, Sedat Karabulut J Sci Food Agric . 2014 Dec;94(15):3134-40. doi: 10.1002/jsfa.6663.
Background:Aflatoxicol (AFL) is one of most the important metabolites of aflatoxin B1 (AFB1). AFL can be formed through enzymatic or synthetic reduction of AFB1. Various experimental and theoretical studies have been focused on the AFB1 due to its high toxicity and carcinogenicity.Results:The selective reduction of AFB1 carbonyls, molecular structure of AFL and its effect on toxicity has been studied here by the density functional theory (DFT) method. Although the toxicity of AFL is 18 times lower than that of AFB1, it has been concluded that both molecular structures have similar potency to form an exo-epoxide (AFEP) analogue which can bind to DNA.Conclusion:Calculations revealed that only one of the three possible tautomers of AFL is stable, both in the gas phase and water. The electronic properties of aflatoxicol are calculated as similar to aflatoxin B1 and this may be an explanation of similar carcinogenicity and toxicity of these compounds, which has been proved by experimental results.
2. Aflatoxins, hydroxylated metabolites, and aflatoxicol from breast muscle of laying hens
I Méndez-Ramírez, E Avila-González, M Díaz-Zaragoza, N C Chilpa-Galván, C M Flores-Ortiz, M Carvajal-Moreno Poult Sci . 2014 Dec;93(12):3152-62. doi: 10.3382/ps.2014-04240.
Aflatoxins (AF) are toxic fungal secondary metabolites that are pathological to animals and humans. This study identified and quantified AF (AFB(1), AFB(2), AFG(1), AFG(2)) and their hydroxylated metabolites (AFM(1), AFM(2), AFP(1)) and aflatoxicol (AFL) from laying hen breast muscles. Aflatoxins pass from cereal feed to the laying hen tissues, causing economic losses, and from there to humans. To detect the passage of AF from feed to hen breast muscle tissues, an experiment that included 25 Hy-Line W36 121-wk-old hens was performed for 8 d. Hens in individual cages were distributed into 3 groups: a control group, with feed free of AFB(1), and 2 experimental groups, with feed spiked with 2 AFB(1) dosages: 30 µg·kg(-1) (low) or 500 µg·kg(-1) (high). The daily feed consumption per hen was recorded and afterward hens were euthanized and breast muscles were collected, weighed, and dried individually. Aflatoxins were extracted by 2 chemical methods and quantified by HPLC. Both methods were validated by lineality (calibration curves), recovery percentage (>80%), limit of detection, and limit of quantification. The AF (µg·kg(-1)) averages recovered in control breast muscles were as follows: AFB(1) (18); AFG(1), AFM(2), and AFL (0); AFG(2) (1.3); AFM(1) (52), and AFP1 (79). Hens fed with feed spiked with 30 µg·kg(-1) of AFB(1) had AFG(1) (16); AFG(2) (72); AFM(1) (0); AFM(2) (18); AFP(1) (145); and AFL (5 µg·kg(-1)). Hens with feed spiked with 500 µg·kg(-1) of AFB(1) had AFG(1) (512); AFG(2) (7); AFM(1) (4,775); AFM(2) (0); AFP(1) (661); and AFL (21 µg·kg(-1)). The best AF extraction method was Qian and Yang's method, modified by adding additional AF from both Supelclean LC18 SPE columns; its limit of detection (0.5 ng·mL(-1)) was lower compared with that of Koeltzow and Tanner, which was 1 ng·mL(-1).
3. Determination of aflatoxicol in human urine by immunoaffinity column clean-up and liquid chromatography
K Andersson, C A Nilsson, B Andersson, A Kussak Chemosphere . 1998 Apr;36(8):1841-8. doi: 10.1016/s0045-6535(97)10036-4.
A method for the determination of aflatoxicol in urine has been developed. The urine samples were cleaned up by an automated procedure using immunoaffinity columns before analysis by high-performance liquid chromatography and fluorescence detection. Post-column derivatization with bromine allowed the simultaneous determination of aflatoxicol and aflatoxins B1, B2, G1, G2, M1, and Q1. Average recovery of aflatoxicol was 99% in the range 4-40 pg ml-1 of spiked urine samples. The relative standard deviations were all between 1% and 3%. The limit of detection was 1 pg ml-1 urine. Authentic samples from exposed feed-factory workers were analysed, but aflatoxin levels were found to be below the detection limit.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H14O6
Molecular Weight (Monoisotopic Mass): 314.079 Da
Molecular Weight (Avergae Mass): 314.2895 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H14O6
Molecular Weight (Monoisotopic Mass): 314.079 Da
Molecular Weight (Avergae Mass): 314.2895 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H14O6
Molecular Weight (Monoisotopic Mass): 314.079 Da
Molecular Weight (Avergae Mass): 314.2895 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C17H14O6
Molecular Weight (Monoisotopic Mass): 314.079 Da
Molecular Weight (Avergae Mass): 314.2895 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
