Keto-pantoyllactone

HCID 39CAS 13031-04-4

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Basic information

Standard SMILES: CC1(C)COC(=O)C1=O
InChIKey: HRTOQFBQOFIFEE-UHFFFAOYSA-N
Molecular formula: C6H8O3
Average molar mass: 128.13 g/mol
Monoisotopic mass: 128.04734411

Names & identifiers

Preferred name: Keto-pantoyllactone
IUPAC: 4,4-dimethyloxolane-2,3-dione
English name: Dihydro-4,4-dimethyl-2,3-furandione
Molecular formula: C6H8O3
Molecular weight: 128.13

Names & synonyms

13031-04-4Keto-pantoyllactoneketopantolactone2,3-Furandione, dihydro-4,4-dimethyl-ketopantoyl lactoneDihydro-4,4-dimethylfuran-2,3-dioneEINECS 235-891-7DTXSID30156448RefChem:794305DTXCID7078939235-891-74,4-Dimethyldihydrofuran-2,3-dione

Show more names

DIHYDRO-44-DIMETHYL-23-FURANDIONEalpha-KetopantolactoneDexpanthenol iMpurity DDexpanthenol Impurity 5Dexpanthenol Impurity 12

Dihydro-4,4-dimethyl-2,3-Furandione4,4-dimethyloxolane-2,3-dione2-dehydropantolactoneMFCD000123312-dehydropantoyl lactone4,4-Dimethyl-2,3-furandione4,4-dimethyl-4,5-dihydrofuran-2,3-dioneDexpanthenol Impurity 3

Database identifiers

CAS: 13031-04-4
PubChem CID: 39
DTXSID: DTXSID30156448
ChEBI: CHEBI:18395
EC Number: 235-891-7
Nikkaji: J27.237J

Properties

Computed structural properties

XLogP: 0.6
Topological polar surface area: 43.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 169

Physicochemical properties

Melting point: 67 · 67-69 °C (lit.)
Boiling point: 125 · 125-126℃ (15 Torr)
Density: 1.152 · 1.152±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: 25 mg/mL, · dichloromethane: soluble25mg/mL, clear, colorless to yellow
form: Solid
color: Pale Beige
InChI: InChI=1S/C6H8O3/c1-6(2)3-9-5(8)4(6)7/h3H2,1-2H3
InChIKey: HRTOQFBQOFIFEE-UHFFFAOYSA-N
SMILES: O1CC(C)(C)C(=O)C1=O
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 335 · H335-H319-H315
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H335-H319-H315
Precautionary statements: P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Applications · 3 items

UsesDihydro-4,4-dimethyl-2,3-furandione is a heterocyclic organic compound, mainly used as a pharmaceutical intermediate.

UsesDihydro-4,4-dimethyl-2,3-furandione is an activated keto compound and its enantioselective hydrogenation was reported. Neutral Rhodium (I) aminophosphine-phosphinite complex calatyzed asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione was reported. Asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione gives D-(-)-pantoyl lactone, a key intermediate in the synthesis of pantothenic acid.

General DescriptionDihydro-4,4-dimethyl-2,3-furandione is an activated keto compound and its enantioselective hydrogenation was reported. Neutral Rhodium (I) aminophosphine-phosphinite complex calatyzed asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione was reported. Asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione gives D-(-)-pantoyl lactone, a key intermediate in the synthesis of pantothenic acid.