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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:14 UTC

Update Date

2022-03-07 02:52:20 UTC

HMDB ID

HMDB0029884

Secondary Accession Numbers

HMDB29884

Metabolite Identification

Common Name

2-C-Methyl-1,4-erythrono-D-lactone

Description

2-C-Methyl-1,4-erythrono-D-lactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 2-C-Methyl-1,4-erythrono-D-lactone has been detected, but not quantified in, several different foods, such as yellow wax beans (Phaseolus vulgaris), red tea, green beans (Phaseolus vulgaris), teas (Camellia sinensis), and pulses. This could make 2-C-methyl-1,4-erythrono-D-lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-C-Methyl-1,4-erythrono-D-lactone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₈O₄

Average Molecular Weight

132.1146

Monoisotopic Molecular Weight

132.042258744

IUPAC Name

3,4-dihydroxy-3-methyloxolan-2-one

Traditional Name

3,4-dihydroxy-3-methyloxolan-2-one

CAS Registry Number

18465-71-9

SMILES

CC1(O)C(O)COC1=O

InChI Identifier

InChI=1S/C5H8O4/c1-5(8)3(6)2-9-4(5)7/h3,6,8H,2H2,1H3

InChI Key

OHTGZAWPVDWARE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029884)
Cytoplasm (HMDB: HMDB0029884)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029884)

Source

Exogenous

Exogenous (HMDB: HMDB0029884)

Food

Food (HMDB: HMDB0029884)

Tea

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0029884)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0029884)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	94290 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	836 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.1	ChemAxon
logS	0.8	ALOGPS
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	27.57 m³·mol⁻¹	ChemAxon
Polarizability	11.64 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]+	127.738	31661259
DarkChem	[M-H]-	121.993	31661259
DeepCCS	[M+H]+	124.434	30932474
DeepCCS	[M-H]-	121.434	30932474
DeepCCS	[M-2H]-	158.007	30932474
DeepCCS	[M+Na]+	133.002	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	134.0	32859911
AllCCS	[M-H]-	122.5	32859911
AllCCS	[M+Na-2H]-	124.7	32859911
AllCCS	[M+HCOO]-	127.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-C-Methyl-1,4-erythrono-D-lactone	CC1(O)C(O)COC1=O	2506.9	Standard polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone	CC1(O)C(O)COC1=O	1112.0	Standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone	CC1(O)C(O)COC1=O	1247.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-C-Methyl-1,4-erythrono-D-lactone,1TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)OCC1O	1264.9	Semi standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone,1TMS,isomer #2	CC1(O)C(=O)OCC1O[Si](C)(C)C	1252.4	Semi standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone,2TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)OCC1O[Si](C)(C)C	1370.1	Semi standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)OCC1O	1495.0	Semi standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone,1TBDMS,isomer #2	CC1(O)C(=O)OCC1O[Si](C)(C)C(C)(C)C	1477.9	Semi standard non polar	33892256
2-C-Methyl-1,4-erythrono-D-lactone,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)OCC1O[Si](C)(C)C(C)(C)C	1798.4	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 - 2-C-Methyl-1,4-erythrono-D-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-36702b5b35d69afb512a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone GC-MS (2 TMS) - 70eV, Positive	splash10-0gi0-9680000000-236c42ab71edb7bfc730	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 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 - 2-C-Methyl-1,4-erythrono-D-lactone 10V, Positive-QTOF	splash10-001i-3900000000-b9d38fa9491ae073c249	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 20V, Positive-QTOF	splash10-00lr-2900000000-f33a119d8314cf832c94	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 40V, Positive-QTOF	splash10-05mo-9000000000-af9fbd69079c3699067f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 10V, Negative-QTOF	splash10-001i-0900000000-b0e8488454abf5430abe	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 20V, Negative-QTOF	splash10-001i-2900000000-4f9e1bf6985a057b84a1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 40V, Negative-QTOF	splash10-0006-9000000000-6005bb31e6d37312d93b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 10V, Positive-QTOF	splash10-00kb-7900000000-3652896c97777efa3f8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 20V, Positive-QTOF	splash10-0005-9100000000-3ca1ac02808f0d0ad15d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 40V, Positive-QTOF	splash10-0005-9000000000-4c1e2a5464e15b71dac3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 10V, Negative-QTOF	splash10-001r-9700000000-a4e9f91a44b164c6eb40	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 20V, Negative-QTOF	splash10-000f-9000000000-927189b444258fb345e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-C-Methyl-1,4-erythrono-D-lactone 40V, Negative-QTOF	splash10-0006-9000000000-a344cc293ff20d5c6c08	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart 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

FDB001119

KNApSAcK ID

Not Available

Chemspider ID

9643928

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11469098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1811971

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 2-C-Methyl-1,4-erythrono-D-lactone (HMDB0029884)

MOL for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

3D MOL for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

3D SDF for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

3D-SDF for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

PDB for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

3D PDB for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

SMILES for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

INCHI for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

Structure for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

3D Structure for HMDB0029884 (2-C-Methyl-1,4-erythrono-D-lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra