Showing Compound alpha-Hydroxyisobutyric acid (FDB022207)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:06 UTC

Update date

2015-10-09 22:29:18 UTC

Primary ID

FDB022207

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-Hydroxyisobutyric acid

Description

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 metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide. [HMDB]

CAS Number

594-61-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(CH3)2COHCOOH	HMDB
alpha-hydroxyisobutanoate	hmdb
alpha-hydroxyisobutanoic acid	hmdb
α-hydroxy-α-methylpropanoate	Generator
α-hydroxy-α-methylpropanoic acid	Generator
α-hydroxy-α-methylpropionate	Generator
α-hydroxy-α-methylpropionic acid	Generator
α-hydroxyisobutanoate	Generator
α-hydroxyisobutanoic acid	Generator
α-hydroxyisobutyrate	Generator
α-hydroxyisobutyric acid	Generator

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

Chemical Formula

C4H8O3

IUPAC name

2-hydroxy-2-methylpropanoic acid

InChI Identifier

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

InChI Key

BWLBGMIXKSTLSX-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

Classification

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 )

Ontology

Lung cancer

Disposition

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-Hydroxyisobutyric acid, 2 TMS, GC-MS Spectrum	splash10-00e9-8900000000-2d2298731d2c1ce975ff	Spectrum
GC-MS	alpha-Hydroxyisobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-bb87a50521380a4f04c0	Spectrum
GC-MS	alpha-Hydroxyisobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00e9-8900000000-2d2298731d2c1ce975ff	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9000000000-af78bdeb830f08b3a6a6	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00su-9610000000-cea13166d0c9b277d7d8	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Hydroxyisobutyric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-8900000000-b51c12e744025b833f31	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9100000000-0d72fcffff267d7bc980	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4l-9000000000-bb87a50521380a4f04c0	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-09121cf499d55d5656ac	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d524fab140880c782425	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-1aadb4e9ee70b665d435	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0udi-0900000000-69f23830b20d34978bed	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-09121cf499d55d5656ac	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0pb9-9600000000-3394a5ec4ff4ff576fcd	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-5fc3362d72c467fb6197	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052f-9000000000-3de5183bd97ccc5072c8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d524fab140880c782425	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-591fd3d7ad484dd6f1ff	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-69f23830b20d34978bed	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-8900000000-f40f4783e4b817b45a70	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-28ad10690e6680bd4046	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0a3b71647acebd936a7e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-7f058188704b24bc8cee	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-40bbfa4d36a4c19902c0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-237ae993c0cc1090dd96	Spectrum

NMR

Type	Description	View
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

11181

ChEMBL ID

CHEMBL1345148

KEGG Compound ID

Not Available

Pubchem Compound ID

11671

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00729

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound alpha-Hydroxyisobutyric acid (FDB022207)

Structure for FDB022207 (alpha-Hydroxyisobutyric acid)