(R)-pantolactone (YMDB00796)

Identification

YMDB ID

YMDB00796

Name

(R)-pantolactone

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

(R)-pantolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review a significant number of articles have been published on (R)-pantolactone.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(3R)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-Furanone
(D)-Pantolactone
(R)-(-)-Pantolactone
(R)-Pantolactone
(R)-Pantoyl lactone
2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, (R)-
2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, D-(-)-
3-Hydroxy-4,4-dimethyldihydro-2(3H)-furanone
D-(-)-Pantoic acid lactone
D-(-)-Pantolactone
D-(-)-Pantolyl lactone
D-(-)Pantoyl lactone
D-1-Hydroxy-2,2-dimethyl-3-butyrolactone
Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone, pantolactone
Pantolyl lactone
Pantothenic lactone
Pantoyl lactone
Pentoyl lactone
Pentoyl lactone clene
2,4-Dihydroxy-3,3-dimethylbutyric acid gamma-lactone
Pantolactone
Pantolactone, (R)-isomer
Pantolactone, (S)-isomer
Pantolactone, 2-(14)C-labeled CPD, (+,-)-isomer

CAS number

599-04-2

Weight

Average: 130.1418
Monoisotopic: 130.062994186

InChI Key

SERHXTVXHNVDKA-BYPYZUCNSA-N

InChI

InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1

IUPAC Name

(3R)-3-hydroxy-4,4-dimethyloxolan-2-one

Traditional IUPAC Name

pantolactone

Chemical Formula

C₆H₁₀O₃

SMILES

CC1(C)COC(=O)[C@@H]1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butan-4-olide (CHEBI:16719 )

Physical Properties

State

Solid

Charge

Melting point

92 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	361 g/L	ALOGPS
logP	0.27	ALOGPS
logP	0.18	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.52 m³·mol⁻¹	ChemAxon
Polarizability	12.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
61 ± 8 µM	Must from Vitis vinifera, cv. Pedro Ximrnez (Sherry Wine)	anaerobic	Baker's yeast	Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356
Conversion Details Here

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
61 ± 15 µM	Must from Vitis vinifera, cv. Pedro Ximrnez (Sherry Wine)	anaerobic	Baker's yeast	Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356
Conversion Details Here

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a73-9100000000-c01e1fe15c775ea2f265	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-0d977bd0da49659e2899	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3900000000-9ed7578033895f0953a2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9000000000-da2602df23cab6ffd4d4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-ed97c835db2ff7d1cb77	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-7900000000-af04c0ae5ec10a5674c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-386ffb816d54724fb91b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-5900000000-b62a08297c563d6245c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9400000000-d9d1d6fe0f2487667d80	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-5cf1d6a6029e544d7206	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-ba7553fe1231679f4b65	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9200000000-c86e58e524d612554a42	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9100000000-934d3d7122639797ca87	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16719
HMDB ID	HMDB0303902
Pubchem Compound ID	439368
Kegg ID	C01012
ChemSpider ID	388488
FOODB ID	FDB029751
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xaf38cb9c>