13360-65-1|3-Ethyl-2,5-dimethylpyrazine| Ambeed

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Quality Control of [ 13360-65-1 ] Purity: 97% SDS Specification

COA

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Product Citations Show More

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

Chemoenzymatic synthesis of 3-ethyl-2, 5-dimethylpyrazine by L-threonine 3-dehydrogenase and 2-amino-3-ketobutyrate CoA ligase/L-threonine aldolase

Motoyama, Tomoharu ; Nakano, Shogo ; Hasebe, Fumihito ; Miyata, Ryo ; Kumazawa, Shigenori ; Miyoshi, Noriyuki , et al.

DOI: 10.1038/s42004-021-00545-8 PubMed ID: 36697628 Commun. Chem.,2021,4(1):108.

Abstract: Pyrazines are typically formed from amino acids and sugars in chemical reactions such as the Maillard reaction. In this study, we demonstrate that 3-ethyl-2,5-dimethylpyrazine can be produced from L-Thr by a simple bacterial operon. We conclude that EDMP is synthesized chemoenzymatically from L-Thr via the condensation reaction of two molecules of aminoacetone and one molecule of acetaldehyde. Aminoacetone is supplied by L-threonine 3-dehydrogenase using L-Thr as a substrate via 2-amino-3-ketobutyrate. Acetaldehyde is supplied by 2-amino-3-ketobutyrate CoA ligase bearing threonine aldolase activity from L-Thr when CoA was at low concentrations. Considering the rate of EDMP production, the reaction intermediate is stable for a certain time, and moderate reaction temperature is important for the synthesis of EDMP. When the precursor was supplied from L-Thr by these enzymes, the yield of EDMP was increased up to 20.2%. Furthermore, we demonstrate that this reaction is useful for synthesizing various alkylpyrazines.

Purchased from AmBeed: 13360-65-1

Product Details of [ 13360-65-1 ]

CAS No. :	13360-65-1
Formula :	C₈H₁₂N₂
M.W :	136.19
SMILES Code :	CC1=CN=C(C)C(CC)=N1
MDL No. :	MFCD00053098
InChI Key :	WHMWOHBXYIZFPF-UHFFFAOYSA-N
Pubchem ID :	25916

Safety of [ 13360-65-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 13360-65-1 ] 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.	1.98
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	1.65

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)	2.03

Application In Synthesis of [ 13360-65-1 ]

* 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 [ 13360-65-1 ]

[ 13360-65-1 ] Synthesis Path-Downstream 1~32

1
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[ 13360-65-1 ]
[ 108-50-9 ]
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[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
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