ChemFOnt: Showing chemical card for alpha-Hydroxyisobutyric acid (CFc000000578)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:00 UTC

Chemfont ID

CFc000000578

Molecule Identification

Common Name

alpha-Hydroxyisobutyric acid

Definition

alpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolized to t-butyl alcohol (TBA) and formaldehyde and oxidized to 2-methyl-1,2-propanediol and alpha-hydroxyisobutyric acid. alpha-Hydroxyisobutyric acid has been used as an aerial bactericide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-2-methylpropionic acid	ChEBI
2-Hydroxy-2-methylpropionsaeure	ChEBI
2-Methyl-2-hydroxypropanoic acid	ChEBI
2-Methyl-2-hydroxypropionsaeure	ChEBI
2-Methyllactic acid	ChEBI
Acetonic acid	ChEBI
Acide 2-hydroxy-2-methylpropanoique	ChEBI
Acido 2-hidroxi-2-metilpropionico	ChEBI
alpha-Hydroxy-alpha-methylpropanoic acid	ChEBI
alpha-Hydroxy-alpha-methylpropionic acid	ChEBI
alpha-Hydroxyisobutanoic acid	ChEBI
HIBA	ChEBI
Hydroxydimethylacetic acid	ChEBI
2-Hydroxy-2-methylpropionate	Generator
2-Methyl-2-hydroxypropanoate	Generator
2-Methyllactate	Generator
Acetonate	Generator
a-Hydroxy-a-methylpropanoate	Generator
a-Hydroxy-a-methylpropanoic acid	Generator
alpha-Hydroxy-alpha-methylpropanoate	Generator
Α-hydroxy-α-methylpropanoate	Generator
Α-hydroxy-α-methylpropanoic acid	Generator
a-Hydroxy-a-methylpropionate	Generator
a-Hydroxy-a-methylpropionic acid	Generator
alpha-Hydroxy-alpha-methylpropionate	Generator
Α-hydroxy-α-methylpropionate	Generator
Α-hydroxy-α-methylpropionic acid	Generator
a-Hydroxyisobutanoate	Generator
a-Hydroxyisobutanoic acid	Generator
alpha-Hydroxyisobutanoate	Generator
Α-hydroxyisobutanoate	Generator
Α-hydroxyisobutanoic acid	Generator
Hydroxydimethylacetate	Generator
a-Hydroxyisobutyrate	Generator
a-Hydroxyisobutyric acid	Generator
alpha-Hydroxyisobutyrate	Generator
Α-hydroxyisobutyrate	Generator
Α-hydroxyisobutyric acid	Generator
a-Hydroxy-isobutyrate	HMDB
a-Hydroxy-isobutyric acid	HMDB
alpha-Hydroxy-isobutyrate	HMDB
Α-hydroxy-isobutyrate	HMDB
Α-hydroxy-isobutyric acid	HMDB
(CH3)2cohcooh	HMDB
2-Hydroxy-2-methylpropanoate	HMDB
2-Hydroxy-2-methylpropanoic acid	HMDB
2-Hydroxyisobutyrate	HMDB
2-Hydroxyisobutyric acid	HMDB
a-HIB	HMDB
alpha-HIB	HMDB
Hydroxyisobutyrate	HMDB
L-2-Methyllactate	HMDB
L-2-Methyllactic acid	HMDB
2-Hydroxyisobutyric acid, lead salt	HMDB
Lead 2-hydroxyisobutyric acid	HMDB
alpha-Hydroxyisobutyric acid	ChEBI

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

2-hydroxy-2-methylpropanoic acid

Traditional Name

acetonate

CAS Registry Number

594-61-6

SMILES

CC(C)(O)C(O)=O

InChI Identifier

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

InChI Key

BWLBGMIXKSTLSX-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

Alpha-hydroxy acid
Tertiary 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

2-hydroxy monocarboxylic acid (CHEBI:50129 )
Hydroxy fatty acids (LMFA01050417 )

Functional Ontology

Physiological effect

Health effect

Respiratory system disorder

Pulmonary disorder

Lung Cancer (HMDB: HMDB0000729)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Saliva (HMDB: HMDB0000729)

Organ

Placenta (HMDB: HMDB0000729)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0000729)

Source

Exogenous

Exogenous (HMDB: HMDB0000729)

Process

Not Available

Role

Environmental role

Environmental contaminant (HMDB: HMDB0000729)

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000238)
Lung Cancer (MarkerDB: MDB00000238)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	378 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	-0.039	ChemAxon
logS	0.56	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-3.7	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	1	ChemAxon
Refractivity	23.55 m³·mol⁻¹	ChemAxon
Polarizability	9.87 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

External Links

HMDB ID

HMDB0000729

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022207

KNApSAcK ID

Not Available

Chemspider ID

11181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3750

PubChem Compound

11671

PDB ID

Not Available

ChEBI ID

50129

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Vogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9.

Showing chemical card for alpha-Hydroxyisobutyric acid (CFc000000578)

MOL for CFc000000578 (alpha-Hydroxyisobutyric acid)

3D MOL for CFc000000578 (alpha-Hydroxyisobutyric acid)

3D SDF for CFc000000578 (alpha-Hydroxyisobutyric acid)

3D-SDF for CFc000000578 (alpha-Hydroxyisobutyric acid)

PDB for CFc000000578 (alpha-Hydroxyisobutyric acid)

3D PDB for CFc000000578 (alpha-Hydroxyisobutyric acid)

SMILES for CFc000000578 (alpha-Hydroxyisobutyric acid)

INCHI for CFc000000578 (alpha-Hydroxyisobutyric acid)

Structure for CFc000000578 (alpha-Hydroxyisobutyric acid)

3D Structure for CFc000000578 (alpha-Hydroxyisobutyric acid)