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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:14 UTC

Update Date

2023-02-21 17:21:55 UTC

HMDB ID

HMDB0032333

Secondary Accession Numbers

HMDB32333

Metabolite Identification

Common Name

4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone

Description

4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone, also known as 4-methyl-4-vinyl-1,4-butanolide or 4-methyl-4-vinylbutyrolactone, 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. 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), black tea, herbal tea, red tea, and grape wine. This could make 4-hydroxy-4-methyl-5-hexenoic acid gamma lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-4-methyl-5-hexenoate g lactone	Generator
4-Hydroxy-4-methyl-5-hexenoate gamma lactone	Generator
4-Hydroxy-4-methyl-5-hexenoate γ lactone	Generator
4-Hydroxy-4-methyl-5-hexenoic acid g lactone	Generator
4-Hydroxy-4-methyl-5-hexenoic acid γ lactone	Generator
4-Methyl-4-vinyl-1,4-butanolide	HMDB
4-Methyl-4-vinylbutyrolactone	HMDB
4-Methyl-5-hexen-4-olide	HMDB
5-Ethenyl-5-methyl-2(3H)-furanone	HMDB
5-Ethenyl-5-methyloxolan-2-one	HMDB
5-Ethenyldihydro-5-methyl-2(3H)-furanone	HMDB
5-Methyl-5-vinyldihydro-2(3H)-furanone	HMDB
Dihydro-5-methyl-5-vinyl-2(3H)-furanone	HMDB
Dihydro-5-methyl-5-vinylfuran-2(3H)-one	HMDB
Laquo gammaraquo -vinyl-laquo gammaraquo -valerolactone	HMDB
Lavander lactone	HMDB
Lavender lactone	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.155

Monoisotopic Molecular Weight

126.068079562

IUPAC Name

5-ethenyl-5-methyloxolan-2-one

Traditional Name

5-ethenyl-5-methyloxolan-2-one

CAS Registry Number

1073-11-6

SMILES

CC1(CCC(=O)O1)C=C

InChI Identifier

InChI=1S/C7H10O2/c1-3-7(2)5-4-6(8)9-7/h3H,1,4-5H2,2H3

InChI Key

QESPSAHXYXIGBG-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
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032333)
Cytoplasm (HMDB: HMDB0032333)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.66 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.22	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	-7.1	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	1	ChemAxon
Refractivity	33.78 m³·mol⁻¹	ChemAxon
Polarizability	13.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.66	31661259
DarkChem	[M-H]-	122.548	31661259
DeepCCS	[M+H]+	125.954	30932474
DeepCCS	[M-H]-	122.389	30932474
DeepCCS	[M-2H]-	159.804	30932474
DeepCCS	[M+Na]+	134.843	30932474
AllCCS	[M+H]+	125.3	32859911
AllCCS	[M+H-H2O]+	120.5	32859911
AllCCS	[M+NH4]+	129.7	32859911
AllCCS	[M+Na]+	131.0	32859911
AllCCS	[M-H]-	125.5	32859911
AllCCS	[M+Na-2H]-	127.7	32859911
AllCCS	[M+HCOO]-	130.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone	CC1(CCC(=O)O1)C=C	1679.1	Standard polar	33892256
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone	CC1(CCC(=O)O1)C=C	978.0	Standard non polar	33892256
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone	CC1(CCC(=O)O1)C=C	1026.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone EI-B (Non-derivatized)	splash10-0bvl-9200000000-288aefec213df99a77a2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone EI-B (Non-derivatized)	splash10-0bvl-9200000000-288aefec213df99a77a2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gdl-9000000000-55b8188b9d924876ed81	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma 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 - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Positive-QTOF	splash10-004i-2900000000-fa61e83a2322102e7fa1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Positive-QTOF	splash10-0kdi-9400000000-9f4df5bc0701e56a4441	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Positive-QTOF	splash10-1000-9000000000-456d2a5525482b95dc80	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Negative-QTOF	splash10-004i-3900000000-173ee627c0b4ffa9718f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Negative-QTOF	splash10-0059-9600000000-1e06bc9a5ae34c41f055	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Negative-QTOF	splash10-002f-9000000000-92debe2684efa4ba31fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Negative-QTOF	splash10-014i-9200000000-caa88bd7cedaf2124bc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Negative-QTOF	splash10-0ugi-9000000000-6cb361c9af7839531572	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Negative-QTOF	splash10-0gbc-9000000000-71460161a8d02092ce26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Positive-QTOF	splash10-0ar0-9300000000-f7141c758cf6863f1f63	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Positive-QTOF	splash10-0a4i-9000000000-a1fc0ad10dc676a37041	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Positive-QTOF	splash10-0uxu-9000000000-471a27dbfa771562fb4b	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+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

FDB004423

KNApSAcK ID

Not Available

Chemspider ID

92625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102550

PDB ID

Not Available

ChEBI ID

52939

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone (HMDB0032333)

MOL for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

3D MOL for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

3D SDF for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

3D-SDF for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

PDB for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

3D PDB for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

SMILES for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

INCHI for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

Structure for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

3D Structure for HMDB0032333 (4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra