MiMeDB: Showing metabocard for ethyl 3-hydroxybutanoate (MMDBc0033458)

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:49:29 UTC

Update Date

2024-10-09 17:18:38 UTC

Metabolite ID

MMDBc0033458

Metabolite Identification

Common Name

ethyl 3-hydroxybutanoate

Description

Ethyl-3-hydroxybutyrate is a volatile ethyl ester found in wine and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. Ethyl-3-hydroxybutyrate is responsible for marshmallow-like aromas. The concentrations of ethyl ester decrease over time as a wine ages due to spontaneous hydrolysis.

Structure

MOL SDF PDB SMILES InChI

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

Molecular Formula

C₆H₁₂O₃

Average Mass

132.1577

Monoisotopic Mass

132.07864425

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

5405-41-4

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	171.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	31.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	319.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	402.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	329.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	328.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1388.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	81.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	624.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	320.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	267.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	187.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	106.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	105.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	429.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	62.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	250.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1031.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	739.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	ethyl 3-hydroxybutanoate_TMS_1	CCOC(=O)CC(C)O[Si](C)(C)C	standard non polar	2025-10-24	2073.36
Gas Chromatography	ethyl 3-hydroxybutanoate_TMS_1	CCOC(=O)CC(C)O[Si](C)(C)C	standard polar	2025-10-24	2303.37

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0039073	ethyl 3-hydroxybutanoate	3-Hydroxybutyric acid	Monoglyceride lipase	Lipid (ester bond) hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

87685

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Antonelli A, Castellari L, Zambonelli C, Carnacini A: Yeast influence on volatile composition of wines. J Agric Food Chem. 1999 Mar;47(3):1139-44. doi: 10.1021/jf9807317. [PubMed:10552428 ]
Patel S, Shibamoto T: Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine. J Agric Food Chem. 2002 Sep 25;50(20):5649-53. doi: 10.1021/jf020337f. [PubMed:12236692 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for ethyl 3-hydroxybutanoate (MMDBc0033458)

MOL for #<Metabolite:0x00007f9aa8a5e250>

3D MOL for #<Metabolite:0x00007f9aa8a5e250>

3D SDF for #<Metabolite:0x00007f9aa8a5e250>

3D-SDF for #<Metabolite:0x00007f9aa8a5e250>

PDB for #<Metabolite:0x00007f9aa8a5e250>

3D PDB for #<Metabolite:0x00007f9aa8a5e250>

SMILES for #<Metabolite:0x00007f9aa8a5e250>

INCHI for #<Metabolite:0x00007f9aa8a5e250>

Structure for #<Metabolite:0x00007f9aa8a5e250>

3D Structure for #<Metabolite:0x00007f9aa8a5e250>