2-Hydroxyisobutyric acid

HCID 11671
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Basic information

CAS
594-61-6
Standard SMILES
CC(C)(O)C(=O)O
InChIKey
BWLBGMIXKSTLSX-UHFFFAOYSA-N
Molecular formula
C4H8O3
Average molar mass
104.1 g/mol
Monoisotopic mass
104.04734412

Overview

2-hydroxyisobutyric acid is a 2-hydroxy monocarboxylic acid that is isobutyric acid bearing a hydroxy substituent at position 2. It is a metabolite of methyl tertiary-butyl ether. It has a role as a human xenobiotic metabolite. It is functionally related to an isobutyric acid. It is a conjugate acid of a 2-hydroxyisobutyrate.

Names & identifiers

Preferred name
2-Hydroxyisobutyric acid
IUPAC
2-hydroxy-2-methylpropanoic acid
English name
2-Hydroxyisobutyric acid
Molecular formula
C4H8O3
Molecular weight
104.1

Names & synonyms

2-HYDROXYISOBUTYRIC ACID594-61-62-Methyllactic acid2-Hydroxy-2-methylpropanoic acidAcetonic acidalpha-Hydroxyisobutyric acidHydroxydimethylacetic acidPropanoic acid, 2-hydroxy-2-methyl-Lactic acid, 2-methyl-alpha-Hydroxyisobutanoic acid2-hydroxy-2-methyl-propanoic acidDTXSID4032954
Show more names
2-hydroxyisobutyrateα-Hydroxyisobutyric acid|á-Hydroxyisobutyric acid2-hydroxy-2-methylpropanoate2-HYDROXY-2-METHYLPROPIONIC ACID(CH3)2COHCOOHMETHYL LACTIC ACID
alpha-Hydroxy-alpha-methylpropanoic acidDMW250U2HFNSC-4505NSC-402158DTXCID2012954CHEBI:50129RefChem:87569209-848-8

Database identifiers

CAS
594-61-6
PubChem CID
11671
DTXSID
DTXSID4032954
ChEMBL
CHEMBL1345148
ChEBI
CHEBI:50129
UNII
DMW250U2HF
EC Number
209-848-8
Nikkaji
J2.707C

Properties

Computed structural properties

XLogP
-0.4
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
7

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]
SpringerMaterials PropertiesBoiling point
LogP · 2 items

-0.36

-0.36

Boiling Point · 2 items

212.00 °C. @ 760.00 mm Hg

212 °C @760 [mm Hg]

Melting Point · 2 items

82.5 °C

82.5 °C

Physicochemical properties

Melting point
76 · 76-80 °C(lit.)
Boiling point
84 °C1.5 · 84 °C1.5 mm Hg(lit.)
Density
11412 · 11412
refractive index
1.4761 · 1.4761 (estimate)
Flash point
114 °C/12mm · 114°C/12mm
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 42% (55 of 131) of reports.

Danger

H315 (53.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 131 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Propanoic acid, 2-hydroxy-2-methyl-

Status: Active Update: 12-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25201

2-Hydroxyisobutyric acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See Butyric acid.
Hazard Classes and CategoriesSkin Irrit. 2 (53.4%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

12 [mg/m3]

130 [mg/m3]

790 [mg/m3]

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29181980
risk_code
37/38-41-36/37/38
Signal word
Danger

Chemistry & industry

Pharmacology

Tissue LocationsPlacenta
Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing InformationPropanoic acid, 2-hydroxy-2-methyl-: ACTIVE
Applications · 4 items

Uses2-Hydroxyisobutyric acid is used as an electrolyte in the separation of the metal ions by on-line cyclic voltammetry. It is also used as a building block for the synthesis of polymers. Its conjugate base, 2-hydroxybutyrate is utilized to catabolize L-threonine as well as synthesize glutathione. Further, it is used as an indicator for the early detection insulin resistance in non-diabetic subjects.

Usesα-Hydroxyisobutyric acid was used as background electrolyte for separation and detection of the metal ions by on-line cyclic voltammetry.

Uses2-Hydroxyisobutyric acid is used as background electrolyte for separation and detection of the metal ions by on-line cyclic voltammetry.

General Descriptionα-Hydroxyisobutyric acid (2-hydroxyisobutyric acid) is the building block for polymer synthesis. It forms complexes with Eu(III) and has been studied by time resolved fluorescence spectroscopy.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北博杰生物科技有限公司0713-2060728 15629612610
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: A 2-hydroxy monocarboxylic acid that is isobutyric acid bearing a hydroxy substituent at position 2. It is a metabolite of methyl tertiary-butyl ether.

Related reactions

175 records
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Compound notes

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