Basic information
- Standard SMILES
CCC(C)(C)C(=O)O- InChIKey
VUAXHMVRKOTJKP-UHFFFAOYSA-N- Molecular formula
- C6H12O2
- Average molar mass
- 116.16 g/mol
- Monoisotopic mass
- 116.08372962
Overview
2,2-dimethylbutyric acid is a branched-chain fatty acid and metabolite of the lactone prodrug simvastatin, whose sodium salt is potentially useful for the treatment of thalassaemias and haemoglobinopathies. It has a role as a metabolite.
Names & identifiers
- Preferred name
- 2,2-Dimethylbutanoic acid
- IUPAC
- 2,2-dimethylbutanoic acid
- English name
- 2,2-Dimethylbutyric acid
- Molecular formula
- C6H12O2
- Molecular weight
- 116.16
Names & synonyms
2,2-Dimethylbutanoic acid2,2-DIMETHYLBUTYRIC ACID595-37-9Dimebutic AcidDTXSID0032811NSC-16045AY606CN05OCHEBI:38649NSC-741804DTXCID8012811ST-20 compoundRefChem:441399
Show more names
NEOHEXANOIC ACIDDiMethylbutyric Aci2,2-Dimethylbutanoic2-Dimethylbutyricacid2,2-Dimethylbuttersαure2,2-two Methyl butyrateDIMETHYLETHYLACETIC ACID
2,2-DMB209-865-0Butanoic acid, 2,2-dimethyl-2,2-dimethyl-butyric acid2,2-dimethyl-butanoic acidButyric acid, 2,2-dimethyl-2.2-Dimethylbutyric aciddimethyl ethyl acetic acid
Database identifiers
- CAS
595-37-9- PubChem CID
- 11684
- DTXSID
DTXSID0032811- ChEMBL
CHEMBL286013- ChEBI
CHEBI:38649- UNII
- AY606CN05O
- EC Number
- 209-865-0
- Nikkaji
- J121.086F
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 94.7
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]
SpringerMaterials PropertiesDensity
LogP1.9
Density0.928 @25 °C
Physicochemical properties
- Melting point
- -14 °C · -14°C
- Boiling point
- 94 · 94-96 °C/5 mmHg (lit.)
- Density
- 0.928 g/mL · 0.928 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.4154(lit.)
- Flash point
- 175 °F · 175 °F
- storage temp.
- Refrigerator
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- pka
- 1 · pK1:5.03 (18°C)
- form
- Liquid
- color
- Clear colorless to pale yellow
- Specific Gravity
- 0.928 · 0.928
- Decomposition
- 176 · 176-178 ºC
- BRN
- 1720666 · 1720666
- InChI
- 1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)
- InChIKey
- VUAXHMVRKOTJKP-UHFFFAOYSA-N
- SMILES
- CCC(C)(C)C(O)=O
- LogP
- 1 · 1-2.3 at 20℃ and pH2.5-6.7
- CAS DataBase Reference
- 595 · 595-37-9(CAS DataBase Reference)
- FDA UNII
- 606 CN05O · AY606CN05O
- NIST Chemistry Reference
- 2 · Butanoic acid, 2,2-dimethyl-(595-37-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37-36
- WGK Germany
- 3 · 3
- HS Code
- 29156000 · 29156000
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 133 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 17-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/5656
Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)
Safety & protection
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- hs_code
- 29156000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37-36
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Description2,2-Dimethylbutyric acid is the intermediate of crucial importance in producing cardiovascular drugs, such as Simvastatin and agricultural chemicals, miticide spiral shell mite ester. It can also be used for rubber, dyestuff, etc. industries simultaneously. All 2,2-Dimethylbutyric acid production processes are that primary isoamyl alcohol and formic acid react under sulfuric acid catalysis. This technique's shortcoming is to produce a large amount of Waste Sulfuric Acids.
Uses2,2-Dimethylbutyrate (DMB) is a potential treatment for thalassemia and hemoglobinopathies.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A branched-chain fatty acid and metabolite of the lactone prodrug simvastatin, whose sodium salt is potentially useful for the treatment of thalassaemias and haemoglobinopathies.
Related reactions
17 records
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