ContaminantDB: 2-Hydroxybutyric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:17:38 UTC

Update Date

2026-04-06 10:16:39 UTC

Accession Number

CHEM003265

Identification

Common Name

2-Hydroxybutyric acid

Class

Small Molecule

Description

2-Hydroxybutyric acid (alpha-hydroxybutyrate) is an organic acid derived from alpha-ketobutyrate. Alpha-ketobutyrate is produced by amino acid catabolism (threonine and methionine) and glutathione anabolism (cysteine formation pathway) and is metabolized to propionyl-CoA and carbon dioxide 2-Hydroxybutyric acid is formed as a by-product during the formation of Alpha-ketobutyrate via a reaction catalyzed by lactate dehydrogenase (LDH) or alpha-hydroxybutyrate dehydrogenase (alpha-HBDH). Alpha-hydroxybutyric acid is primarily produced in mammalian hepatic tissues that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification of xenobiotics in the liver can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway (which forms methionine) into the transsulfuration pathway (which forms cystathionine). 2-Hydroxybutyrate is released as a byproduct when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate. 2-hydroxybutyrate is an early marker for both insulin resistance and impaired glucose regulation that appears to arise due to increased lipid oxidation and oxidative stress 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as cerebral lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (1, 1, 2, 3).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Industrial/Workplace Toxin
Mammal Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxybutanoic acid	ChEBI
alpha-Hydroxybutanoic acid	ChEBI
alpha-Hydroxybutyric acid	ChEBI
2-Hydroxybutanoate	Generator
a-Hydroxybutanoate	Generator
a-Hydroxybutanoic acid	Generator
alpha-Hydroxybutanoate	Generator
Α-hydroxybutanoate	Generator
Α-hydroxybutanoic acid	Generator
a-Hydroxybutyrate	Generator
a-Hydroxybutyric acid	Generator
alpha-Hydroxybutyrate	Generator
Α-hydroxybutyrate	Generator
Α-hydroxybutyric acid	Generator
2-Hydroxybutyrate	Generator
(RS)-2-Hydroxybutyrate	HMDB
(RS)-2-Hydroxybutyric acid	HMDB
2-Hydroxy-butanoate	HMDB
2-Hydroxy-butanoic acid	HMDB
2-Hydroxy-DL-butyrate	HMDB
2-Hydroxy-DL-butyric acid	HMDB
2-Hydroxy-N-butyrate	HMDB
2-Hydroxy-N-butyric acid	HMDB
a-Hydroxy-N-butyrate	HMDB
a-Hydroxy-N-butyric acid	HMDB
alpha-Hydroxy-N-butyrate	HMDB
alpha-Hydroxy-N-butyric acid	HMDB
DL-2-Hydroxybutanoate	HMDB
DL-2-Hydroxybutanoic acid	HMDB
DL-a-Hydroxybutyrate	HMDB
DL-a-Hydroxybutyric acid	HMDB
DL-alpha-Hydroxybutyrate	HMDB
DL-alpha-Hydroxybutyric acid	HMDB
2-Hydroxybutyric acid, (R)-isomer	HMDB
2-Hydroxybutyric acid, monosodium salt	HMDB
2-Hydroxybutyric acid, (+-)-isomer	HMDB
2-Hydroxybutyric acid, monosodium salt, (+-)-isomer	HMDB
(+/-)a-hydoxy butyrate	HMDB
(+/-)a-hydoxy butyric acid	HMDB
(+/-)alpha-hydoxy butyrate	HMDB
(+/-)α-hydoxy butyrate	HMDB
(+/-)α-hydoxy butyric acid	HMDB
2-Hydroxybutyric acid	MeSH

Chemical Formula

C₄H₈O₃

Average Molecular Mass

104.105 g/mol

Monoisotopic Mass

104.047 g/mol

CAS Registry Number

600-15-7

IUPAC Name

Not Available

Traditional Name

α-hydroxybutyric acid

SMILES

CCC(O)C(O)=O

InChI Identifier

InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)

InChI Key

AFENDNXGAFYKQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid
Alpha-hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
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

hydroxybutyric acid (CHEBI:1148 )
2-hydroxy monocarboxylic acid (CHEBI:1148 )
Hydroxy fatty acids (LMFA01050004 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Prostate

Pathways

Name	SMPDB Link	KEGG Link
Biotinidase Deficiency	SMP00174	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	44.2°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	484 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	0.051	ChemAxon
logS	0.67	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.36 m³·mol⁻¹	ChemAxon
Polarizability	9.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-1910000000-3bc9898b26df33cad244	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-4d935da8e593ec61fd96	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-1910000000-3bc9898b26df33cad244	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-9000000000-0d95c1179b1b00650601	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00v0-9520000000-598a2bd61c303327bd8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4j-9200000000-e3b371c29b9ebed3199b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9700000000-bccfada2c97e04d34417	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-9000000000-4d935da8e593ec61fd96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-2900000000-3c7915ea71886873f024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zfr-7900000000-d91c840306a06d4ea513	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9500000000-8f04a5941997004743d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-cef703dc6f30af7834a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-1e7e6e8a895c4c1d51db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-4900000000-d0907a0b08e0d829ceca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-d826b54f814ac185b4db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-3727124ed618f038b514	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000008

FooDB ID

FDB021867

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

47130

BioCyc ID

Not Available

METLIN ID

3783

PDB ID

Not Available

Wikipedia Link

2-Hydroxybutyric_acid

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15749359

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=164303

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=168632

4. Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.

5. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.

6. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.

7. Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.

8. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64.

9. Landaas S, Pettersen JE: Clinical conditions associated with urinary excretion of 2-hydroxybutyric acid. Scand J Clin Lab Invest. 1975 May;35(3):259-66.