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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:06 UTC

Update Date

2023-02-21 17:22:56 UTC

HMDB ID

HMDB0032988

Secondary Accession Numbers

HMDB32988

Metabolite Identification

Common Name

5-Hydroxymaltol

Description

5-Hydroxymaltol 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. 5-Hydroxymaltol has been detected, but not quantified in, a few different foods, such as barleys (Hordeum vulgare), breakfast cereal, and cereals and cereal products. This could make 5-hydroxymaltol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 5-Hydroxymaltol.

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-Methyl-3,5-dihydroxy-4H-pyran-4-one	HMDB
3,5-Dihydroxy-2-methyl-4-pyrone	HMDB
3,5-Dihydroxy-2-methyl-4H-pyran-4-one	HMDB
3,5-Dihydroxy-2-methyl-4H-pyran-4-one (hydroxymaltol)	HMDB
3,5-Dihydroxy-6-methyl-4-pyrone	HMDB
Hydroxymaltol	HMDB
Pentamethyl-cyclopentaphosphane	HMDB

Chemical Formula

C₆H₆O₄

Average Molecular Weight

142.1094

Monoisotopic Molecular Weight

142.02660868

IUPAC Name

3,5-dihydroxy-2-methyl-4H-pyran-4-one

Traditional Name

5-hydroxymaltol

CAS Registry Number

1073-96-7

SMILES

CC1=C(O)C(=O)C(O)=CO1

InChI Identifier

InChI=1S/C6H6O4/c1-3-5(8)6(9)4(7)2-10-3/h2,7-8H,1H3

InChI Key

SSSNQLHKSUJJTE-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032988)
Cytoplasm (HMDB: HMDB0032988)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032988)

Source

Exogenous

Exogenous (HMDB: HMDB0032988)

Food

Food (HMDB: HMDB0032988)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0032988)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032988)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	184 - 184.5 °C	Not Available
Boiling Point	346.00 to 347.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	5507 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.123 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	68.3 g/L	ALOGPS
logP	-0.42	ALOGPS
logP	0.3	ChemAxon
logS	-0.32	ALOGPS
pKa (Strongest Acidic)	8.37	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.69 m³·mol⁻¹	ChemAxon
Polarizability	12.53 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]+	129.679	31661259
DarkChem	[M-H]-	124.672	31661259
DeepCCS	[M+H]+	129.86	30932474
DeepCCS	[M-H]-	126.576	30932474
DeepCCS	[M-2H]-	163.759	30932474
DeepCCS	[M+Na]+	138.844	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	133.0	32859911
AllCCS	[M+Na]+	134.3	32859911
AllCCS	[M-H]-	123.2	32859911
AllCCS	[M+Na-2H]-	124.9	32859911
AllCCS	[M+HCOO]-	126.7	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.	2.13 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6185 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	50.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1585.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	331.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	205.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	118.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	376.9 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	552.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	154.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	720.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	279.2 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	1111.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	587.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.1 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	213.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxymaltol	CC1=C(O)C(=O)C(O)=CO1	2238.1	Standard polar	33892256
5-Hydroxymaltol	CC1=C(O)C(=O)C(O)=CO1	1161.7	Standard non polar	33892256
5-Hydroxymaltol	CC1=C(O)C(=O)C(O)=CO1	1184.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxymaltol,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)C(O)=CO1	1519.4	Semi standard non polar	33892256
5-Hydroxymaltol,1TMS,isomer #2	CC1=C(O)C(=O)C(O[Si](C)(C)C)=CO1	1572.1	Semi standard non polar	33892256
5-Hydroxymaltol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)C(O[Si](C)(C)C)=CO1	1578.0	Semi standard non polar	33892256
5-Hydroxymaltol,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(O)=CO1	1808.8	Semi standard non polar	33892256
5-Hydroxymaltol,1TBDMS,isomer #2	CC1=C(O)C(=O)C(O[Si](C)(C)C(C)(C)C)=CO1	1848.5	Semi standard non polar	33892256
5-Hydroxymaltol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(O[Si](C)(C)C(C)(C)C)=CO1	2108.3	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 - 5-Hydroxymaltol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7900000000-77b9b505d3c126671ed8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymaltol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-5890000000-1cae50d74246ca973a71	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxymaltol 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 - 5-Hydroxymaltol 10V, Positive-QTOF	splash10-0006-0900000000-c30d13ad8eda37dcee40	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 20V, Positive-QTOF	splash10-0006-1900000000-f3c3c22221a8b62fe2fe	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 40V, Positive-QTOF	splash10-0a7i-9100000000-70c8597f9c0f33926a99	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 10V, Negative-QTOF	splash10-0006-0900000000-8e17719a88a9f2d7bb78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 20V, Negative-QTOF	splash10-0006-6900000000-31f2a664c8d65d10c5ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 40V, Negative-QTOF	splash10-0a59-9100000000-551597aac232c5e88fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 10V, Positive-QTOF	splash10-0006-0900000000-0c99f72c61ed7201e39f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 20V, Positive-QTOF	splash10-052f-9600000000-f18b663946402358979c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 40V, Positive-QTOF	splash10-0a4l-9000000000-2ea9ada6faeaf66c7718	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 10V, Negative-QTOF	splash10-0006-1900000000-deb742e89467c13c8806	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 20V, Negative-QTOF	splash10-052f-9100000000-83647a564edc1eeadcff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxymaltol 40V, Negative-QTOF	splash10-0a4l-9000000000-6accb45caab51d2f2563	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB010977

KNApSAcK ID

C00055673

Chemspider ID

63795

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Hydroxymaltol

METLIN ID

Not Available

PubChem Compound

70627

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1057291

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 5-Hydroxymaltol (HMDB0032988)

MOL for HMDB0032988 (5-Hydroxymaltol)

3D MOL for HMDB0032988 (5-Hydroxymaltol)

3D SDF for HMDB0032988 (5-Hydroxymaltol)

3D-SDF for HMDB0032988 (5-Hydroxymaltol)

PDB for HMDB0032988 (5-Hydroxymaltol)

3D PDB for HMDB0032988 (5-Hydroxymaltol)

SMILES for HMDB0032988 (5-Hydroxymaltol)

INCHI for HMDB0032988 (5-Hydroxymaltol)

Structure for HMDB0032988 (5-Hydroxymaltol)

3D Structure for HMDB0032988 (5-Hydroxymaltol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra