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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:56:58 UTC

Update Date

2023-02-21 17:28:13 UTC

HMDB ID

HMDB0040409

Secondary Accession Numbers

HMDB40409

Metabolite Identification

Common Name

Ethyl (±)-3-hydroxybutyrate

Description

Ethyl (±)-3-hydroxybutyrate, also known as ethyl b-hydroxybutyric acid, 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-hydroxybutyrate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Ethyl (±)-3-hydroxybutyrate.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl beta-hydroxybutyrate	ChEBI
Ethyl b-hydroxybutyrate	Generator
Ethyl b-hydroxybutyric acid	Generator
Ethyl beta-hydroxybutyric acid	Generator
Ethyl β-hydroxybutyrate	Generator
Ethyl β-hydroxybutyric acid	Generator
Ethyl (±)-3-hydroxybutyric acid	Generator
Ethyl 3-hydroxybutyrate	HMDB
FEMA 3428	HMDB
Ethyl 3-hydroxybutyric acid	Generator
(S)-Ethyl 3-hydroxybutyrate	MeSH
(R)-Ethyl 3-hydroxybutyrate	MeSH

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

ethyl 3-hydroxybutanoate

Traditional Name

ethyl 3-hydroxybutanoate

CAS Registry Number

35608-64-1

SMILES

CCOC(=O)CC(C)O

InChI Identifier

InChI=1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3

InChI Key

OMSUIQOIVADKIM-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:87685 )

Ontology

Prickly pear (FooDB: FOOD00440)

Tea

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	170.00 to 175.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	159200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.098 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	299 g/L	ALOGPS
logP	0.39	ALOGPS
logP	0.12	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-2.6	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	4	ChemAxon
Refractivity	32.98 m³·mol⁻¹	ChemAxon
Polarizability	14.02 Å³	ChemAxon
Number of Rings	0	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]+	128.705	31661259
DarkChem	[M-H]-	124.931	31661259
DeepCCS	[M+H]+	132.342	30932474
DeepCCS	[M-H]-	129.857	30932474
DeepCCS	[M-2H]-	166.26	30932474
DeepCCS	[M+Na]+	141.271	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.6	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	133.5	32859911
AllCCS	[M+HCOO]-	136.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl (??)-3-hydroxybutyrate	CCOC(=O)CC(C)O	1643.4	Standard polar	33892256
Ethyl (??)-3-hydroxybutyrate	CCOC(=O)CC(C)O	953.7	Standard non polar	33892256
Ethyl (??)-3-hydroxybutyrate	CCOC(=O)CC(C)O	998.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl (??)-3-hydroxybutyrate,1TMS,isomer #1	CCOC(=O)CC(C)O[Si](C)(C)C	1094.9	Semi standard non polar	33892256
Ethyl (??)-3-hydroxybutyrate,1TBDMS,isomer #1	CCOC(=O)CC(C)O[Si](C)(C)C(C)(C)C	1302.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate EI-B (Non-derivatized)	splash10-0079-9100000000-2cfa78e1dd2a78c6c2bf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate EI-B (Non-derivatized)	splash10-0079-9100000000-2cfa78e1dd2a78c6c2bf	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-056v-9000000000-14ac82ba5f2fa0560c9b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate GC-MS (1 TMS) - 70eV, Positive	splash10-01ei-9800000000-87a106098a2fa722c6e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl (±)-3-hydroxybutyrate 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-hydroxybutyrate 10V, Positive-QTOF	splash10-014i-3900000000-821e1d58f00dc134bc41	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 20V, Positive-QTOF	splash10-014i-9400000000-6acb5f514fae0d85b0ef	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 40V, Positive-QTOF	splash10-0006-9000000000-d91a0f109a961f30b130	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 10V, Negative-QTOF	splash10-001r-8900000000-325a24d608d0e012af42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 20V, Negative-QTOF	splash10-000i-9300000000-7f99ffb2ccdae5cb99fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 40V, Negative-QTOF	splash10-0a4u-9000000000-01dee6fc7aae342f2cd4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 10V, Positive-QTOF	splash10-014s-9300000000-a3022f712b79ae845136	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 20V, Positive-QTOF	splash10-0002-9000000000-5c2e49dd5c0a75ce8a0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 40V, Positive-QTOF	splash10-0007-9000000000-1f8d547cae4e101d9c42	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 10V, Negative-QTOF	splash10-001a-9200000000-77ff4602f5c0979f4de2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 20V, Negative-QTOF	splash10-052o-9000000000-6baceb257f6b1a134c52	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl (±)-3-hydroxybutyrate 40V, Negative-QTOF	splash10-066u-9000000000-e3acf6e8dfc5bb17bce3	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	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

FDB020141

KNApSAcK ID

C00050444

Chemspider ID

56334

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62572

PDB ID

Not Available

ChEBI ID

87685

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056311

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-hydroxybutyrate (HMDB0040409)

MOL for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

3D MOL for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

3D SDF for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

3D-SDF for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

PDB for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

3D PDB for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

SMILES for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

INCHI for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

Structure for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

3D Structure for HMDB0040409 (Ethyl (±)-3-hydroxybutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra