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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:00 UTC

Update Date

2023-02-21 17:22:52 UTC

HMDB ID

HMDB0032966

Secondary Accession Numbers

HMDB32966

Metabolite Identification

Common Name

Furaneol acetate

Description

Furaneol acetate belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Furaneol acetate is a sweet, baked, and bread tasting compound. Based on a literature review very few articles have been published on Furaneol acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.826   4.187   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    7   11                                                  
CONECT    5    2    8   11                                                  
CONECT    6    3    9   12                                                  
CONECT    7    4    8   10                                                  
CONECT    8    5    7   12                                                  
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    4    5                                                       
CONECT   12    6    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Furaneol acetic acid	Generator
3(2H)-Furanone, 4-hydroxy-2,5-dimethyl-, acetate	HMDB
4-(Acetyloxy)-2,5-dimethyl-3(2H)-furanone	HMDB
4-Acetoxy-2,5-dimethyl-3(2H)-furanone	HMDB
4-Acetoxy-2,5-dimethyl-3(2H)furanone	HMDB
4-Hydroxy-2,5-dimethyl-3(2H)-furanone acetate	HMDB
FEMA 3797	HMDB
2,5-Dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetic acid	Generator

Chemical Formula

C₈H₁₀O₄

Average Molecular Weight

170.1626

Monoisotopic Molecular Weight

170.057908808

IUPAC Name

2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetate

Traditional Name

2,5-dimethyl-4-oxo-5H-furan-3-yl acetate

CAS Registry Number

4166-20-5

SMILES

CC1OC(C)=C(OC(C)=O)C1=O

InChI Identifier

InChI=1S/C8H10O4/c1-4-7(10)8(5(2)11-4)12-6(3)9/h4H,1-3H3

InChI Key

VPKIUOQJQJVLRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

3-furanone
Vinylogous ester
Enol ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032966)
Cytoplasm (HMDB: HMDB0032966)

Source

Exogenous

Exogenous (HMDB: HMDB0032966)

Food

Food (HMDB: HMDB0032966)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032966)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	243.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	10010 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.368 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	30.8 g/L	ALOGPS
logP	0.53	ALOGPS
logP	0.12	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.44 m³·mol⁻¹	ChemAxon
Polarizability	16.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.005	31661259
DarkChem	[M-H]-	132.824	31661259
DeepCCS	[M+H]+	135.239	30932474
DeepCCS	[M-H]-	131.41	30932474
DeepCCS	[M-2H]-	168.643	30932474
DeepCCS	[M+Na]+	144.183	30932474
AllCCS	[M+H]+	136.6	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	135.2	32859911
AllCCS	[M+Na-2H]-	136.4	32859911
AllCCS	[M+HCOO]-	137.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.87 minutes	32390414
Predicted by Siyang on May 30, 2022	12.243 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1537.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	237.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	483.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	463.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	930.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1266.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	100.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furaneol acetate	CC1OC(C)=C(OC(C)=O)C1=O	1661.8	Standard polar	33892256
Furaneol acetate	CC1OC(C)=C(OC(C)=O)C1=O	1120.1	Standard non polar	33892256
Furaneol acetate	CC1OC(C)=C(OC(C)=O)C1=O	1236.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Furaneol acetate,1TMS,isomer #1	CC(=O)OC1=C(C)OC(C)=C1O[Si](C)(C)C	1370.7	Semi standard non polar	33892256
Furaneol acetate,1TMS,isomer #1	CC(=O)OC1=C(C)OC(C)=C1O[Si](C)(C)C	1441.1	Standard non polar	33892256
Furaneol acetate,1TBDMS,isomer #1	CC(=O)OC1=C(C)OC(C)=C1O[Si](C)(C)C(C)(C)C	1631.7	Semi standard non polar	33892256
Furaneol acetate,1TBDMS,isomer #1	CC(=O)OC1=C(C)OC(C)=C1O[Si](C)(C)C(C)(C)C	1636.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Furaneol acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-95f65bee28726395c727	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furaneol acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furaneol acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 10V, Positive-QTOF	splash10-00di-0900000000-9ab0862a4a627d059d20	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 20V, Positive-QTOF	splash10-00b9-2900000000-6b3f68bc43ea933a71f3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 40V, Positive-QTOF	splash10-02td-9200000000-b6ea668343fcade4a7b0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 10V, Negative-QTOF	splash10-016r-2900000000-3e2d99e20632c4cdb325	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 20V, Negative-QTOF	splash10-0a6r-5900000000-2dcc9e1ea46a97ea9102	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 40V, Negative-QTOF	splash10-0a4i-9200000000-6d4c69db79f77b483cfe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 10V, Positive-QTOF	splash10-00fr-1900000000-db4a7f42cd07bef1e5b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 20V, Positive-QTOF	splash10-0096-8900000000-3bb280b2507229791d0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 40V, Positive-QTOF	splash10-0006-9000000000-e5a85d419289a243d51d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 10V, Negative-QTOF	splash10-014i-0900000000-bf9c845e7a39f51ef4bb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 20V, Negative-QTOF	splash10-0a4i-9400000000-9238efa5367f0209d068	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furaneol acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-b3b46eedef814d0a0ff5	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010953

KNApSAcK ID

Not Available

Chemspider ID

55270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61334

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1106051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Furaneol acetate (HMDB0032966)

MOL for HMDB0032966 (Furaneol acetate)

3D MOL for HMDB0032966 (Furaneol acetate)

3D SDF for HMDB0032966 (Furaneol acetate)

3D-SDF for HMDB0032966 (Furaneol acetate)

PDB for HMDB0032966 (Furaneol acetate)

3D PDB for HMDB0032966 (Furaneol acetate)

SMILES for HMDB0032966 (Furaneol acetate)

INCHI for HMDB0032966 (Furaneol acetate)

Structure for HMDB0032966 (Furaneol acetate)

3D Structure for HMDB0032966 (Furaneol acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra