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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:24 UTC
Update Date2019-07-23 06:09:08 UTC
HMDB IDHMDB0031619
Secondary Accession Numbers
  • HMDB31619
Metabolite Identification
Common Name2-Phenyl-2-butenal
Description(E)-2-Phenyl-2-butenal is found in tea. (E)-2-Phenyl-2-butenal is a flavouring ingredient. (E)-2-Phenyl-2-butenal is a odorous component of black tea Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid); In addition to being one of the building blocks in protein synthesis, it is the most widespread neurotransmitter in brain function, as an excitatory neurotransmitter and as a precursor for the synthesis of GABA in GABAergic neurons.
Structure
Data?1563862148
Synonyms
ValueSource
(2Z)-2-Phenyl-2-butenalHMDB
2-Butenal, 2-phenylHMDB
2-Phenyl-2-buten-1-alHMDB
2-Phenyl-crotonaldehydeHMDB
2-Phenylacetaldehyde, alpha -ethylideneHMDB
2-Phenylbut-2-enalHMDB
2-PhenylbutenalHMDB
2-PhenylcrotonaldehydeHMDB
a-Ethylidene-benzeneacetaldehydeHMDB
a-Ethylidenebenzeneacetaldehyde, 9ciHMDB
alpha -EthylidenbenzeneacetaldehydeHMDB
alpha -Ethylidene benzene acetaldehydeHMDB
alpha -Ethylidene-phenylacetaldehydeHMDB
alpha-Ethylidene-benzeneacetaldehydeHMDB
alpha-EthylidenebenzeneacetaldehydeHMDB
alpha-PhenylcrotonaldehydeHMDB
FEMA 3224HMDB
Chemical FormulaC10H10O
Average Molecular Weight146.1858
Monoisotopic Molecular Weight146.073164942
IUPAC Name(2E)-2-phenylbut-2-enal
Traditional Name(2E)-2-phenylbut-2-enal
CAS Registry Number4411-89-6
SMILES
C\C=C(\C=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O/c1-2-9(8-11)10-6-4-3-5-7-10/h2-8H,1H3/b9-2-
InChI KeyDYAOGZLLMZQVHY-MBXJOHMKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Styrene
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP2.74ALOGPS
logP2.43ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.49 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available134.67931661259
DarkChem[M-H]-PredictedNot Available130.93731661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-0912d35ae2db4c141a842017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-2900000000-0912d35ae2db4c141a842021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-fcacddcba2fa79261f5c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2900000000-2d55ec5f0c3cd9cdaacf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9600000000-ba47697cec40b1ee8dd22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd79bb539d105536d8cd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-0ee4c3daf24682a7ac9b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-3c0d3d5838245f22a5852016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-9a45b2a0a353c990f2502021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-d4d605ed34049b8fa9f12021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-8900000000-f4594bf718db18fbccda2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2ebe16f6e5066e5177ab2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-5b3a2e3171a4a0f3c78e2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-9800000000-27ad211b4608bea66f602021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008257
KNApSAcK IDNot Available
Chemspider ID4934706
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6429333
PDB IDNot Available
ChEBI ID89904
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .