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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:06 UTC

Update Date

2023-02-21 17:21:17 UTC

HMDB ID

HMDB0031735

Secondary Accession Numbers

HMDB31735

Metabolite Identification

Common Name

Ethyl maltol

Description

Ethyl maltol, also known as 3-hydroxy-2-ethyl-4-pyrone or indium ethylmaltol, is a member of the class of compounds known as pyranones and derivatives. These compounds contain a pyran ring which bears a ketone. Ethyl maltol is soluble (in water) and a very weakly acidic compound (based on its pKa). Ethyl maltol is an organic compound that is a common flavourant in some confectioneries. It is related to the more common flavorant maltol by replacement of the methyl group with an ethyl group. It is a white solid with a sweet smell that can be described as caramelized sugar and cooked fruit (Wikipedia ). Ethyl maltol is a flavour enhancer, flavouring agent, and a sweetener. It has 4-6X the potency of 3-hydroxy-2-methyl-4H-pyran-4-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Ethyl-3-hydroxy-4-pyrone	HMDB
2-Ethylpyromeconic acid	HMDB
3-Hydroxy-2-ethyl-1,4-pyrone	HMDB
3-Hydroxy-2-ethyl-4-pyrone	HMDB, MeSH
3-Hydroxy-2-ethyl-4H-pyran-4-one	HMDB
3-Hydroxy-2-ethyl-laquo gammaraquo -pyrone	HMDB
e637	HMDB
FEMA 3487	HMDB
Ilekudinoside a	HMDB
Veltol plus	HMDB
Ethylmaltol	MeSH, HMDB
Indium ethylmaltol	MeSH, HMDB

Chemical Formula

C₇H₈O₃

Average Molecular Weight

140.1366

Monoisotopic Molecular Weight

140.047344122

IUPAC Name

2-ethyl-3-hydroxy-4H-pyran-4-one

Traditional Name

ethyl maltol

CAS Registry Number

4940-11-8

SMILES

CCC1=C(O)C(=O)C=CO1

InChI Identifier

InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3

InChI Key

YIKYNHJUKRTCJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031735)
Cytoplasm (HMDB: HMDB0031735)

Source

Endogenous

Endogenous (HMDB: HMDB0031735)

Exogenous

Food

Food (HMDB: HMDB0031735)

Exogenous (HMDB: HMDB0031735)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031735)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	90 - 91 °C	Not Available
Boiling Point	289.00 to 290.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	24230 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.630	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	58.4 g/L	ALOGPS
logP	0.34	ALOGPS
logP	1.07	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.25 m³·mol⁻¹	ChemAxon
Polarizability	13.5 Å³	ChemAxon
Number of Rings	1	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]+	127.99	31661259
DarkChem	[M-H]-	124.979	31661259
DeepCCS	[M+H]+	134.102	30932474
DeepCCS	[M-H]-	131.309	30932474
DeepCCS	[M-2H]-	168.057	30932474
DeepCCS	[M+Na]+	143.091	30932474
AllCCS	[M+H]+	128.1	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	132.6	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	126.3	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	129.8	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.	2.97 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9307 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1401.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	340.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	349.0 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	463.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	756.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	330.3 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	1023.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	297.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	412.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	292.8 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	90.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl maltol	CCC1=C(O)C(=O)C=CO1	1905.5	Standard polar	33892256
Ethyl maltol	CCC1=C(O)C(=O)C=CO1	1163.7	Standard non polar	33892256
Ethyl maltol	CCC1=C(O)C(=O)C=CO1	1173.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl maltol,1TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(=O)C=CO1	1353.9	Semi standard non polar	33892256
Ethyl maltol,1TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C=CO1	1627.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl maltol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vo-7900000000-76867d3703f3c854f893	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl maltol GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-8910000000-f84883a6e552d25dbb8f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl maltol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl maltol 10V, Positive-QTOF	splash10-0006-0900000000-e4ed3eb28b3f1958c103	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl maltol 40V, Positive-QTOF	splash10-00di-9000000000-8a4bd0cc447badd31408	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl maltol 20V, Positive-QTOF	splash10-004l-1900000000-8a11dc4b0e615d9e43a9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 10V, Positive-QTOF	splash10-0006-0900000000-9b8b6ea9166c562f4c04	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 20V, Positive-QTOF	splash10-0006-2900000000-352cec1e0913cc4ce95e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 40V, Positive-QTOF	splash10-0006-9100000000-7ef4d63ccf78564b6830	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 10V, Negative-QTOF	splash10-000i-1900000000-80cc07e29097652798f5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 20V, Negative-QTOF	splash10-052r-5900000000-512dc846e01abb868b1d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 40V, Negative-QTOF	splash10-0k96-9100000000-3c73ccd7471d0f22b2ce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 10V, Negative-QTOF	splash10-000i-1900000000-769dae173863b66d0676	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 20V, Negative-QTOF	splash10-000i-9800000000-d71174a6586b3aec630d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 40V, Negative-QTOF	splash10-0ktf-9000000000-4bf79e9b1f58b6f43b51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 10V, Positive-QTOF	splash10-006x-0900000000-01450ae969df68fc3458	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 20V, Positive-QTOF	splash10-0006-9400000000-e5b1f23d3f9cf5044141	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl maltol 40V, Positive-QTOF	splash10-0f6x-9000000000-e33841ce2e31d06b12e8	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)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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+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

FDB008403

KNApSAcK ID

Not Available

Chemspider ID

19804

KEGG Compound ID

C20362

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl maltol

METLIN ID

Not Available

PubChem Compound

21059

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004172

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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

Showing metabocard for Ethyl maltol (HMDB0031735)

MOL for HMDB0031735 (Ethyl maltol)

3D MOL for HMDB0031735 (Ethyl maltol)

3D SDF for HMDB0031735 (Ethyl maltol)

3D-SDF for HMDB0031735 (Ethyl maltol)

PDB for HMDB0031735 (Ethyl maltol)

3D PDB for HMDB0031735 (Ethyl maltol)

SMILES for HMDB0031735 (Ethyl maltol)

INCHI for HMDB0031735 (Ethyl maltol)

Structure for HMDB0031735 (Ethyl maltol)

3D Structure for HMDB0031735 (Ethyl maltol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra