NP-MRD: Showing NP-Card for Propyl propionate (NP0045524)

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Record Information

Version

2.0

Created at

2022-03-17 19:21:25 UTC

Updated at

2022-03-17 19:21:25 UTC

NP-MRD ID

NP0045524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Propyl propionate

Description

Propyl propionate, also known as fema 2958, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Propyl propionate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Propyl propionate is a sweet, bitter, and chemical tasting compound. Outside of the human body, Propyl propionate has been detected, but not quantified in, a few different foods, such as apples, black elderberries, and sweet cherries. This could make propyl propionate a potential biomarker for the consumption of these foods. Propyl propionate, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, and crohn's disease; propyl propionate has also been linked to the inborn metabolic disorder celiac disease. Propyl propionate is found in Fragaria ananassa and Tagetes minuta. Propyl propionate was first documented in 2005 (PMID: 15691743). A propanoate ester resulting from the formal condensation of the hydroxy group of propanol with the carboxy group of propanoic acid (PMID: 19746921) (PMID: 28332665) (PMID: 23870484) (PMID: 19555224) (PMID: 23991713) (PMID: 25307263).

Structure

MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
N-Propyl N-propionate	ChEBI
N-Propyl propanoate	ChEBI
N-Propyl propionate	ChEBI
Propanoic acid, propyl ester	ChEBI
Propionic acid N-propyl ester	ChEBI
Propionic acid, propyl ester	ChEBI
Propyl ester OF propanoic acid	ChEBI
Propyl propanoate	ChEBI
N-Propyl N-propionic acid	Generator
N-Propyl propanoic acid	Generator
N-Propyl propionic acid	Generator
Propanoate, propyl ester	Generator
Propionate N-propyl ester	Generator
Propionate, propyl ester	Generator
Propyl ester OF propanoate	Generator
Propyl propanoic acid	Generator
Propyl propionic acid	Generator
FEMA 2958	HMDB
Propyl-propanoate	HMDB
Propylester kyseliny propionove	HMDB

Chemical Formula

C₆H₁₂O₂

Average Mass

116.1583 Da

Monoisotopic Mass

116.08373 Da

IUPAC Name

propyl propanoate

Traditional Name

propyl propanoate

CAS Registry Number

106-36-5

SMILES

CCCOC(=O)CC

InChI Identifier

InChI=1S/C6H12O2/c1-3-5-8-6(7)4-2/h3-5H2,1-2H3

InChI Key

MCSINKKTEDDPNK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fragaria x ananassa	LOTUS Database	35616633
Prunus avium	FooDB	J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tagetes minuta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010412 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.81	ALOGPS
logP	1.5	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.31 m³·mol⁻¹	ChemAxon
Polarizability	13.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030059

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001367

KNApSAcK ID

Not Available

Chemspider ID

7515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Propyl_propanoate

METLIN ID

Not Available

PubChem Compound

7803

PDB ID

Not Available

ChEBI ID

89828

Good Scents ID

Not Available

References

General References

Cometto PM, Daele V, Idir M, Lane SI, Mellouki A: Reaction rate coefficients of OH radicals and Cl atoms with ethyl propanoate, n-propyl propanoate, methyl 2-methylpropanoate, and ethyl n-butanoate. J Phys Chem A. 2009 Oct 8;113(40):10745-52. doi: 10.1021/jp9061708. [PubMed:19746921 ]
Neurock M, Tao Z, Chemburkar A, Hibbitts DD, Iglesia E: Theoretical insights into the sites and mechanisms for base catalyzed esterification and aldol condensation reactions over Cu. Faraday Discuss. 2017 Apr 28;197:59-86. doi: 10.1039/c6fd00226a. [PubMed:28332665 ]
Mochalski P, Sponring A, King J, Unterkofler K, Troppmair J, Amann A: Release and uptake of volatile organic compounds by human hepatocellular carcinoma cells (HepG2) in vitro. Cancer Cell Int. 2013 Jul 17;13(1):72. doi: 10.1186/1475-2867-13-72. [PubMed:23870484 ]
Buzzini P, Romano S, Turchetti B, Vaughan A, Pagnoni UM, Davoli P: Production of volatile organic sulfur compounds (VOSCs) by basidiomycetous yeasts. FEMS Yeast Res. 2005 Feb;5(4-5):379-85. doi: 10.1016/j.femsyr.2004.10.011. [PubMed:15691743 ]
Wise PM, Toczydlowski SE, Zhao K, Wysocki CJ: Temporal integration in nasal lateralization of homologous propionates. Inhal Toxicol. 2009 Aug;21(10):819-27. doi: 10.1080/08958370802555880. [PubMed:19555224 ]
Povarov VG, Keresten AA: Propyl propionate methanolysis kinetics: experiment and modeling. J Phys Chem A. 2013 Sep 26;117(38):9115-9. doi: 10.1021/jp403967b. Epub 2013 Sep 17. [PubMed:23991713 ]
Mochalski P, Al-Zoairy R, Niederwanger A, Unterkofler K, Amann A: Quantitative analysis of volatile organic compounds released and consumed by rat L6 skeletal muscle cells in vitro. J Breath Res. 2014 Oct 13;8(4):046003. doi: 10.1088/1752-7155/8/4/046003. [PubMed:25307263 ]
Rosier E, Loix S, Develter W, Van de Voorde W, Tytgat J, Cuypers E: The Search for a Volatile Human Specific Marker in the Decomposition Process. PLoS One. 2015 Sep 16;10(9):e0137341. doi: 10.1371/journal.pone.0137341. eCollection 2015. [PubMed:26375029 ]
Rosier E, Loix S, Develter W, Van de Voorde W, Cuypers E, Tytgat J: Differentiation between decomposed remains of human origin and bigger mammals. J Forensic Leg Med. 2017 Aug;50:28-35. doi: 10.1016/j.jflm.2017.06.003. Epub 2017 Jun 19. [PubMed:28686981 ]

Showing NP-Card for Propyl propionate (NP0045524)

MOL for NP0045524 (Propyl propionate)

3D MOL for NP0045524 (Propyl propionate)

3D SDF for NP0045524 (Propyl propionate)

3D-SDF for NP0045524 (Propyl propionate)

PDB for NP0045524 (Propyl propionate)

3D PDB for NP0045524 (Propyl propionate)

SMILES for NP0045524 (Propyl propionate)

INCHI for NP0045524 (Propyl propionate)

Structure for NP0045524 (Propyl propionate)

3D Structure for NP0045524 (Propyl propionate)