Showing Compound Card for Beta-Phenylpropionic acid (CDB005771)

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Record Information
Version1.0
Created at2020-04-27 16:54:57 UTC
Updated at2021-01-04 18:49:15 UTC
CannabisDB IDCDB005771
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBeta-Phenylpropionic acid
DescriptionHydrocinnamic acid, also known as 3-phenylpropanoic acid or dihydrocinnamic acid, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Hydrocinnamic acid can be prepared from cinnamic acid by hydrogenation. Hydrocinnamic acid is a weakly acidic compound (based on its pKa). It exists as a white, crystalline solid with a sweet, floral scent at room temperature and a sweet, rose, and cinnamon-like taste. Because of its pleasant odor, hydrocinnamic acid is used frequently as an additive in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps. Hydrocinnamic acid is also used in the food industry to preserve and maintain the original aroma quality of frozen foods. Hydrocinnamic acid is also added to food for technological purposes in a wide variety including manufacturing, processing, preparation, treatment, packaging, transportation or storage, and food additives. Hydrocinnamic acid is used as a sweetener as well to sweeten food and can be found in tabletop sweeteners. It is commonly used as flavoring for toothpastes and mouthwashes in addition to providing floral scents and possible fruity, minty, spearmint, strawberry, lychee, and herbal flavorings. Hydrocinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Hydrocinnamic acid has been detected, but not quantified in, several different foods, such as raspberries, raspberry, guava fruit, Vitis vinifera L., papaya, strawberry fruit, cinnamon, cassia leaf, cheddar cheese, cocoa, beer, cognac, white wine, red wine, special wine, rose apple, mushroom, cloudberry, Boletus edulis, fresh mango, licorice and labdanum. This could make hydrocinnamic acid a potential biomarker for the consumption of these foods. Hydrocinnamic acid is one of the volatile compounds found in cannabis smoke and is generated during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Phenyl-propionic acidChEBI
3-Phenylpropanoic acidChEBI
3-PhenylpropionsaeureChEBI
3PPChEBI
Benzenepropanoic acidChEBI
Benzenepropionic acidChEBI
Benzylacetic acidChEBI
beta-Phenylpropionic acidChEBI
Dihydrocinnamic acidChEBI
HydrozimtsaeureChEBI
PhenylpropanoateChEBI
3-PhenylpropanoateKegg
3-Phenylpropionic acidKegg
3-Phenyl-propionateGenerator
BenzenepropanoateGenerator
BenzenepropionateGenerator
BenzylacetateGenerator
b-PhenylpropionateGenerator
b-Phenylpropionic acidGenerator
beta-PhenylpropionateGenerator
Β-phenylpropionateGenerator
Β-phenylpropionic acidGenerator
DihydrocinnamateGenerator
Phenylpropanoic acidGenerator
3-PhenylpropionateGenerator
HydrocinnamateGenerator
3-Phenyl-N-propionateHMDB
3-Phenyl-N-propionic acidHMDB
Omega-phenylpropanoateHMDB
Omega-phenylpropanoic acidHMDB
W-PhenylpropanoateHMDB
W-Phenylpropanoic acidHMDB
3-Phenylpropionic acid, sodium saltHMDB
3-Phenyl propionic acidHMDB
Phenylpropionic acidHMDB
beta-Phenylpropanoic acidHMDB
Β-phenylpropanoic acidHMDB
Ω-phenylpropanoic acidHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.17
Monoisotopic Molecular Weight150.0681
IUPAC Name3-phenylpropanoic acid
Traditional Name3-phenylpropionic acid
CAS Registry Number501-52-0
SMILES
OC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
InChI KeyXMIIGOLPHOKFCH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.9 mg/mLNot Available
logP1.84HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.84ALOGPS
logP2.06ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.97 m³·mol⁻¹ChemAxon
Polarizability15.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MSBeta-Phenylpropionic acid, 1 TMS, GC-MS Spectrumsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udl-9600000000-685b73e7f17a8be64f76Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-6b08d11fe7d8828ea0b4Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-271b64525610b577f87cSpectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udl-9300000000-faf8506e70502be88599Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0f6x-9800000000-6d3e3634b1663556c431Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1940000000-4bdbde45f0dac2b3ec59Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MSBeta-Phenylpropionic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-2910000000-b14f8ca2c631d87eb834Spectrum
Predicted GC-MSBeta-Phenylpropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6x-8900000000-bbfe334bf7c6f8fab3edSpectrum
Predicted GC-MSBeta-Phenylpropionic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-9510000000-32f6cb9988fbfb2c022eSpectrum
Predicted GC-MSBeta-Phenylpropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBeta-Phenylpropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBeta-Phenylpropionic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a60402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e58962012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06e2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-56bd4f79b41d2e676de82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052b-2900000000-b4b013241fad936a60402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9100000000-21973848f978136e58962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0900000000-b8bb01617b312682874b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-5d1cbf0e902fef2a674d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f783831562012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66feb2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ce2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd5375468372596922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ce2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd5375468372596922015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000764
DrugBank IDDB02024
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008271
KNApSAcK IDC00052317
Chemspider ID10181339
KEGG Compound IDC05629
BioCyc ID3-PHENYLPROPIONATE
BiGG IDNot Available
Wikipedia LinkPhenylpropanoic_acid
METLIN ID4153
PubChem Compound107
PDB IDNot Available
ChEBI ID28631
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91