13925-07-0|2-Ethyl-3,5-dimethylpyrazine| Ambeed

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Quality Control of [ 13925-07-0 ] Purity: 98% +(isomers mixture) SDS Specification

COA

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Product Citations Show More

Identification of compounds that contribute to aroma liking of whole wheat bread

Pham, Theresa ; Tello, Edisson ; Peterson, Devin G ;

DOI: 10.1016/j.foodres.2025.116192 Food Res. Int.,2025,116192.

Abstract: Whole wheat bread is recommended as part of a healthy diet, but its consumption remains below recommended levels, partly due to poor flavor quality. The influence of aroma compound compositions on bread preference was examined. Targeted gas chromatography/tandem mass spectrometry flavoromics analysis was applied to identify compounds that impacted the aroma liking of whole wheat bread. The chemical profiles for 39 reported odorants across 16 whole wheat bread samples were modeled against consumer liking scores (n = 97) with good fit (R²Y = 0.886) and predictive ability (Q² = 0.758). The most predictive and positively correlated compounds of aroma liking were identified as 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-hydroxy-2-methyl-4-pyrone, 2,3-butanedione, 1-furfuryl pyrrole, furfuryl alcohol, and 2-acetyl-1-pyrroline. Aroma recombination testing further confirmed that the addition of these compounds to the bread resulted in a significantly preferred sample compared to the control (p = 0.002). In summary, 6 out of 39 odors detected in whole wheat bread were reported to impact liking and provide a basis to further optimize product acceptance and promote consumption.

Keywords: Whole wheat bread ; Consumer acceptance ; Aroma liking ; Targeted chemical analysis ; Gas chromatography/tandem mass spectrometry

Purchased from AmBeed: 13925-07-0

Impact of lipase and lipoxygenase activity on the aroma profile of whole wheat bread

Pham, Theresa ; Tello, Edisson ; Peterson, Devin G ;

DOI: 10.1016/j.foodres.2025.116191 Food Res. Int.,2025,116191.

Abstract: Whole wheat flour is prone to lipid oxidation during storage and during the breadmaking process that can negatively impact the flavor profile. The impact of flour enzymatic lipid oxidation on aroma formation in whole wheat bread was investigated. Bread was made from two types of flour, a lipase/lipoxygenase knock-out and the corresponding wild-sibling control, stored at -40 °C (nonaged) and 37 °C (aged) for 8 weeks. Descriptive sensory analysis identified five key aroma attributes of the bread samples: fermented/yeasty, cardboard, fruity, roasty, and bran. A comprehensive gas chromatography-olfactometry analysis allowed the identification and quantification of twenty-nine odor compounds at levels above the odor threshold values. The knock-out of lipase and lipoxygenase activities led to a reduction in lipid oxidation compounds, which was associated with a decrease in cardboard-like off-flavors. Additionally, the knock-out samples reported an increased intensity for fermented/yeasty and fruity attributes related to the high concentrations of 2-phenyl ethanol, ethyl hexanoate, and ethyl heptanoate, as compared to the wild-sibling control samples. Finally, descriptive analysis of aroma recombination models corroborated the analytical findings, showing similar changes in aroma profiles as compared to the differences observed in the bread samples This study highlights the significant role of enzymatic lipid oxidation in shaping the aroma of whole wheat bread and provides insights into modifying aroma profiles through enzymatic control.

Keywords: Whole wheat bread ; Lipase/lipoxygenase knock-out ; Enzymatic lipid oxidation pathway ; Descriptive analysis ; Sensory-guided approach

Purchased from AmBeed: 13925-07-0

Characterization and Profiling of Key Odorants in Roasted Hybrid American-European Hazelnuts

Booth, Megan ; Tello, Edisson ; Peterson, Devin G ;

DOI: 10.1021/acs.jafc.4c05302 PubMed ID: 39258874 J. Agric. Food Chem.,2024,72(38):21144-21151.

Abstract: American-European hybrid hazelnuts (Corylus americana × Corylus avellana) are an emerging crop in the Upper Midwest of the United States that have been reported to have unique sensory characteristics compared to traditionally grown European hazelnuts. In this study, key odor-active compounds in a roasted hybrid hazelnut variety (C. americana × C. avellana) were identified and profiled across different hybrid hazelnut varietals to understand sensory differences. Gas chromatography/mass spectrometry/olfactometry analysis identified 33 odorants with high flavor dilution factors (FD ≥ 16) in the roasted hybrid hazelnut, including 2-acetylpyrazine and 2-aminoacetophenone as first reported hazelnut odorants. Descriptive sensory analysis profiles of the roasted hazelnut and an aroma recombination model consisting of 27 odorants quantified above their odor detection thresholds were not significantly different for the six evaluated attributes, confirming the aroma contribution of the identified odorants. Variation in all 33 aroma-active compounds across 12 hybrid and two European hazelnut varieties was visualized through principal component analysis and related to aroma profiles previously characterized by consumers.

Keywords: American-European hybrid hazelnuts ; gas chromatography/olfactometry ; aroma extract dilution analysis ; aroma recombination ; targeted chemical profiling

Purchased from AmBeed: 13925-07-0 ; 13360-65-1

Identification of Compounds That Contribute to Consumer Aroma Liking of Roasted American-European Hybrid Hazelnuts

Booth, Megan ; Tello, Edisson ; Peterson, Devin G ;

DOI: 10.1021/acs.jafc.4c05303 PubMed ID: 39261019 J. Agric. Food Chem.,2024,72(38):21136-21143.

Abstract: New interspecific hybrid hazelnut crosses between American (Corylus americana) and European (Corylus avellana)hazelnuts are being developed to support a commercial industry in the Midwest region of the United States. In this study, volatilecompounds that impact consumer aroma liking of roasted hybrid hazelnuts (C. americana × C. avellana) were investigated bytargeted and nontargeted GC/MS flavoromics. Chemical profiles from 10 roasted hybrid hazelnut samples were modeled withconsumer aroma liking scores by orthogonal partial least-squares with good fit and predictive performance (R² ≥ 0.92, Q² ≥ 0.82,RMSE^CV = 0.2). Top ranked predictors positively correlated with liking included 12 aroma compounds and 4 profiled volatiles forthe targeted and nontargeted methods, respectively. Sensory recombination testing of hazelnut samples with addition of the 12predictive odorants was preferred by consumers (p < 0.001, Δ aroma liking = 2.2 on 9-point scale) and perceived as more roasty,nutty, and sweet compared to the control (p < 0.05). Addition of the 4 predictive volatiles at subthreshold levels also was preferred(p = 0.02) and perceived as less earthy and mushroom like than the control (p < 0.05).

Keywords: American−European hybrid hazelnuts ; consumer acceptance ; aroma liking ; flavoromics ; volatile profiling

Purchased from AmBeed: 13925-07-0 ; 13360-65-1

Aroma Analysis of Whole Wheat Bread: Impact of Enzymatic Lipid Oxidation and Identification of Drivers of Liking

Pham, Theresa Nguyet ;

Abstract: Whole grains have been widely recognized as an important component of a healthy diet. A major factor limiting consumption of whole grain productsis inferior flavor quality, which is characterized by negative attributes such as cardboard aromas and bitter taste. A number of these negative sensory attributes in whole grains have been attributed to lipid oxidation pathways. However, limited information is known regarding the impact of enzymatic lipid oxidation pathways on the overall flavor profile and consumer acceptability of whole grain products. The overall goal of this project is to understand the aroma formation from enzymatic lipid oxidation pathways and chemical drivers of liking for whole wheat bread aroma. Whole wheat flour is prone to lipid oxidation from the enzymatic action of lipase and lipoxygenase. In the first phase of this project, a sensory-guided technique through chromatography/mass spectrometry/olfactometry (GC/MS/O) was utilized to examine the impact of enzyme activity on aroma formation in whole wheat bread. Bread made from non-aged lipase/lipoxygenase knock-out (KO), aged lipase/lipoxygenase knock-out (KO), non-aged wild-sibling control (WS), and aged wild-sibling control flour samples (WS) were analyzed. Twenty-nine odor compounds were identified and quantified above their odor threshold values. Descriptive sensory analysis (DA) revealed five main attributes of the bread samples: fermented/yeasty, cardboard, fruity, roasty, and bran. Knock-out of the lipase and lipoxygenase activity reported a reduction in lipid oxidation compound formation during flour storage, which aligned with a lower perceived cardboard intensity. Additionally, the knock-out samples reported an increased fermented/yeasty and fruity perception related to the high concentration of 2-phenylethanol, ethyl hexanoate, and ethyl heptanoate, when compared to the wild-sibling control samples. Sensory analysis of the recombination models also supported similar changes in the aroma profile in comparison to the bread samples. Consumption of whole wheat bread is limited by inferior flavor quality. In the second phase of this project aroma compounds that impact the consumer acceptance of whole wheat bread were investigated. Targeted gas chromatography/tandem mass spectrometry (GC-MS/MS) of 40 aroma compounds across 16 whole wheat bread samples were modeled against consumer aroma liking scores (n = 97) by orthogonal partial least squares (OPLS) with good fit (R2Y = 0. 895) and predictive ability (Q 2 = 0.796). The most predictive and positively correlated compounds of aroma liking were identified as 4- hydroxy-2,5-dimethyl-3(2H)-furanone, maltol, 5-hydroxymethylfurfural, 2,3-butanedione, 1-furfurylpyrrole, furfuryl alcohol, and 2-acetyl-1-pyrroline. Aroma recombination testing confirmed that the sample with the addition of the seven compounds was significantly preferred (p = 0.002) compared to the control bread sample. In summary, an improved understanding of aroma formation impacted by enzymatic lipid oxidation pathways was characterized in whole wheat bread. Additionally, a select group of aroma compounds was reported for the first time to impact consumer liking. These results can be utilized to provide better guidance in crop breeding, processing, and selection of wheat varieties to improve flavor quality and promote the consumption of whole grain products.

Purchased from AmBeed: 13925-07-0

Product Details of [ 13925-07-0 ]

CAS No. :	13925-07-0
Formula :	C₈H₁₂N₂
M.W :	136.19
SMILES Code :	CCC1=C(C)N=C(C)C=N1
MDL No. :	MFCD00047392
InChI Key :	JZBCTZLGKSYRSF-UHFFFAOYSA-N
Pubchem ID :	26334

Safety of [ 13925-07-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H227-H302
Precautionary Statements:	P280

Computational Chemistry of [ 13925-07-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	41.74
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	25.78 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.95
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.52
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.66
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.55
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.02
Solubility	1.3 mg/ml ; 0.00955 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.67
Solubility	2.91 mg/ml ; 0.0214 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.19
Solubility	0.0883 mg/ml ; 0.000649 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.05 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.11

Application In Synthesis of [ 13925-07-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 13925-07-0 ]

[ 13925-07-0 ] Synthesis Path-Downstream 1~19

1
[ 38557-72-1 ]
[ 74-96-4 ]
[ 13925-07-0 ]

References: [1]European Journal of Organic Chemistry,2010,p. 2687 - 2695.

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[ 109-08-0 ]
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[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-74-4 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 15707-34-3 ]