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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:18:28 UTC

Update Date

2023-02-21 17:28:54 UTC

HMDB ID

HMDB0041616

Secondary Accession Numbers

HMDB41616

Metabolite Identification

Common Name

Propyl levulinate

Description

Propyl levulinate belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Propyl levulinate is a sweet and caramellic tasting compound. Based on a literature review very few articles have been published on Propyl levulinate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Propyl levulinic acid	Generator
4-Oxopentanoic acid, 9ci	HMDB
Propyl 4-oxopentanoate	HMDB
Propyl ester	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.197

Monoisotopic Molecular Weight

158.094294311

IUPAC Name

propyl 4-oxopentanoate

Traditional Name

propyl 4-oxopentanoate

CAS Registry Number

645-67-0

SMILES

CCCOC(=O)CCC(C)=O

InChI Identifier

InChI=1S/C8H14O3/c1-3-6-11-8(10)5-4-7(2)9/h3-6H2,1-2H3

InChI Key

QOSMNYMQXIVWKY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Fatty acid ester
Fatty acyl
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Caramellic

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041616)
Cytoplasm (HMDB: HMDB0041616)

Source

Exogenous

Exogenous (HMDB: HMDB0041616)

Food

Food (HMDB: HMDB0041616)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0041616)

Biological role

Nutrient (HMDB: HMDB0041616)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	220.00 to 221.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	15080 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.947 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.41 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.96	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	17.54	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.13 m³·mol⁻¹	ChemAxon
Polarizability	17.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.278	31661259
DarkChem	[M-H]-	134.384	31661259
DeepCCS	[M+H]+	138.168	30932474
DeepCCS	[M-H]-	135.093	30932474
DeepCCS	[M-2H]-	172.18	30932474
DeepCCS	[M+Na]+	147.184	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.6	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	142.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.61 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5708 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1804.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	419.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	480.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	64.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	953.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1055.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	331.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	321.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	50.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Propyl levulinate	CCCOC(=O)CCC(C)=O	1843.5	Standard polar	33892256
Propyl levulinate	CCCOC(=O)CCC(C)=O	1083.9	Standard non polar	33892256
Propyl levulinate	CCCOC(=O)CCC(C)=O	1175.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Propyl levulinate,1TMS,isomer #1	CCCOC(=O)CC=C(C)O[Si](C)(C)C	1359.7	Semi standard non polar	33892256
Propyl levulinate,1TMS,isomer #1	CCCOC(=O)CC=C(C)O[Si](C)(C)C	1315.6	Standard non polar	33892256
Propyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCCC)O[Si](C)(C)C	1324.0	Semi standard non polar	33892256
Propyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCCC)O[Si](C)(C)C	1320.9	Standard non polar	33892256
Propyl levulinate,1TBDMS,isomer #1	CCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1569.8	Semi standard non polar	33892256
Propyl levulinate,1TBDMS,isomer #1	CCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1528.6	Standard non polar	33892256
Propyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCCC)O[Si](C)(C)C(C)(C)C	1521.7	Semi standard non polar	33892256
Propyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCCC)O[Si](C)(C)C(C)(C)C	1512.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Propyl levulinate EI-B (Non-derivatized)	splash10-0006-9100000000-34c91c962a120e792e12	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Propyl levulinate EI-B (Non-derivatized)	splash10-0006-9100000000-34c91c962a120e792e12	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-914862039bd66e32ced3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 10V, Positive-QTOF	splash10-052f-4900000000-4093b74b7b5a0218c80b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 20V, Positive-QTOF	splash10-0006-9100000000-2276440da102112d1d34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 40V, Positive-QTOF	splash10-0006-9000000000-168121b3656011c32723	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 10V, Negative-QTOF	splash10-0a4j-6900000000-7778c727a69451f2f698	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 20V, Negative-QTOF	splash10-05mk-9600000000-000b782eab720d913ff1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 40V, Negative-QTOF	splash10-0005-9000000000-4559a56487cffc55d4f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 10V, Negative-QTOF	splash10-0a4j-9100000000-06dbc916e86b6b56b95b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 20V, Negative-QTOF	splash10-002b-9000000000-ec1669600ab09aeeceba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 40V, Negative-QTOF	splash10-0a4l-9000000000-ff2decdb41528d67c862	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 10V, Positive-QTOF	splash10-059y-9100000000-3067e32a65206ab0f46b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 20V, Positive-QTOF	splash10-0007-9000000000-484005e4fa325b4e03b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl levulinate 40V, Positive-QTOF	splash10-0006-9000000000-b3b8c2b51f91a56aee9e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021776

KNApSAcK ID

Not Available

Chemspider ID

191778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

221069

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1586481

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Propyl levulinate (HMDB0041616)

MOL for HMDB0041616 (Propyl levulinate)

3D MOL for HMDB0041616 (Propyl levulinate)

3D SDF for HMDB0041616 (Propyl levulinate)

3D-SDF for HMDB0041616 (Propyl levulinate)

PDB for HMDB0041616 (Propyl levulinate)

3D PDB for HMDB0041616 (Propyl levulinate)

SMILES for HMDB0041616 (Propyl levulinate)

INCHI for HMDB0041616 (Propyl levulinate)

Structure for HMDB0041616 (Propyl levulinate)

3D Structure for HMDB0041616 (Propyl levulinate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra