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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:44 UTC

Update Date

2023-02-21 17:20:42 UTC

HMDB ID

HMDB0031509

Secondary Accession Numbers

HMDB31509

Metabolite Identification

Common Name

Ethyl (±)-3-hydroxyhexanoate

Description

Ethyl (±)-3-hydroxyhexanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Ethyl (±)-3-hydroxyhexanoate is a citrus, fresh, and fruity tasting compound. Ethyl (±)-3-hydroxyhexanoate is found, on average, in the highest concentration within red wine. Ethyl (±)-3-hydroxyhexanoate has also been detected, but not quantified in, several different foods, such as alcoholic beverages, asian pears (Pyrus pyrifolia), citrus, and fruits. This could make ethyl (±)-3-hydroxyhexanoate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethyl (±)-3-hydroxyhexanoate.

Structure

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

COMPND    HMDB0031509
HETATM    1  C1  UNL     1      -2.942   1.795   0.255  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.533   0.473  -0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.321  -0.111   0.380  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.988  -1.405  -0.288  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.689  -1.146  -1.623  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.076  -2.200   0.390  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.365  -1.507   0.494  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.312  -2.122   1.060  1.00  0.00           O  
HETATM    9  O3  UNL     1       1.628  -0.236   0.022  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.932   0.321   0.189  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.981   1.712  -0.402  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.475   1.625   1.224  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.683   2.256  -0.428  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.108   2.495   0.352  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.342  -0.252  -0.276  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.258   0.676  -1.417  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.514   0.628   0.373  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.637  -0.235   1.438  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.926  -2.032  -0.260  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.266  -1.347  -1.743  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.273  -2.455   1.411  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.237  -3.124  -0.202  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.689  -0.359  -0.248  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.125   0.327   1.288  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.429   2.418   0.342  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.971   2.086  -0.690  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.679   1.718  -1.281  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    6   19
CONECT    5   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl (±)-3-hydroxyhexanoic acid	Generator
3-Hydroxyhexanoic acid ethyl ester	HMDB
Ethyl 3-hydroxyhexanoate	HMDB
Ethyl hydroxy-3-hexanoate	HMDB
FEMA 3545	HMDB
Ethyl 3-hydroxy-hexanoic acid	Generator

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

ethyl 3-hydroxyhexanoate

Traditional Name

ethyl 3-hydroxyhexanoate

CAS Registry Number

2305-25-1

SMILES

CCCC(O)CC(=O)OCC

InChI Identifier

InChI=1S/C8H16O3/c1-3-5-7(9)6-8(10)11-4-2/h7,9H,3-6H2,1-2H3

InChI Key

LYRIITRHDCNUHV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty acid ethyl ester (CHEBI:23997 )
Wax monoesters (LMFA07010516 )
a small molecule (ETHYL-S-3-HYDROXYHEXANOATE )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031509)
Cytoplasm (HMDB: HMDB0031509)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031509)

Source

Endogenous

Endogenous (HMDB: HMDB0031509)

Plant

Plant (HMDB: HMDB0031509)

Exogenous

Food

Food (HMDB: HMDB0031509)

Beverage

Fermented beverage

Red wine (FooDB: FOOD00911)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Pome

Asian pear (FooDB: FOOD00291)

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

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	101.00 to 102.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	17480 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.117 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	38.3 g/L	ALOGPS
logP	1.32	ALOGPS
logP	1.08	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	15	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.11 m³·mol⁻¹	ChemAxon
Polarizability	17.81 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.641	31661259
DarkChem	[M-H]-	135.863	31661259
DeepCCS	[M+H]+	137.927	30932474
DeepCCS	[M-H]-	135.659	30932474
DeepCCS	[M-2H]-	172.091	30932474
DeepCCS	[M+Na]+	147.084	30932474
AllCCS	[M+H]+	140.1	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	143.7	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	139.1	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	143.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OCC	1872.5	Standard polar	33892256
Ethyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OCC	1133.2	Standard non polar	33892256
Ethyl (??)-3-hydroxyhexanoate	CCCC(O)CC(=O)OCC	1174.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl (??)-3-hydroxyhexanoate,1TMS,isomer #1	CCCC(CC(=O)OCC)O[Si](C)(C)C	1242.3	Semi standard non polar	33892256
Ethyl (??)-3-hydroxyhexanoate,1TBDMS,isomer #1	CCCC(CC(=O)OCC)O[Si](C)(C)C(C)(C)C	1457.8	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 (±)-3-hydroxyhexanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00g3-9100000000-b0d9fa483326528031c8	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxyhexanoate GC-MS (1 TMS) - 70eV, Positive	splash10-00bm-9310000000-99afec036676702efd21	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 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 - Ethyl (±)-3-hydroxyhexanoate 10V, Positive-QTOF	splash10-01ox-3900000000-8a1daff13592aac44aae	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 20V, Positive-QTOF	splash10-00ke-9500000000-6fd15129ac83a33a89d5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 40V, Positive-QTOF	splash10-0006-9000000000-75590577be06daabb9ca	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 10V, Negative-QTOF	splash10-0bt9-3900000000-9a5f4cc90e2d0999fb36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 20V, Negative-QTOF	splash10-08g4-9500000000-3d6fbb4e82c8bcb050fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 40V, Negative-QTOF	splash10-0007-9100000000-4315d38987ef2680fe78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 10V, Negative-QTOF	splash10-052r-9600000000-73510e94b576f3a06a94	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 20V, Negative-QTOF	splash10-052o-9000000000-83e6ee89c46e90fec108	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 40V, Negative-QTOF	splash10-052f-9000000000-b2a6c07297e3c6c6884a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 10V, Positive-QTOF	splash10-06di-9300000000-9a068be9d137b9c0b74e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 20V, Positive-QTOF	splash10-0005-9000000000-b5bce077521005b4cc0c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxyhexanoate 40V, Positive-QTOF	splash10-0006-9000000000-7f67472fb1de7626ecbd	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008100

KNApSAcK ID

C00053045

Chemspider ID

55232

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61293

PDB ID

Not Available

ChEBI ID

23997

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020221

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 Ethyl (±)-3-hydroxyhexanoate (HMDB0031509)

MOL for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

3D MOL for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

3D SDF for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

3D-SDF for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

PDB for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

3D PDB for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

SMILES for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

INCHI for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

Structure for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

3D Structure for HMDB0031509 (Ethyl (±)-3-hydroxyhexanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra