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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:52:19 UTC

Update Date

2021-09-23 23:52:19 UTC

HMDB ID

HMDB0303161

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Acetoin

Description

Constituent of butter and produced by many microorganisms [DFC] Acetoin is a colorless or pale yellow to green yellow liquid with a pleasant, buttery odor. Acetoin is used as an external energy store by a number of fermentive bacteria. Acetoin, along with diacetyl, is one of the compounds giving butter its characteristic flavor. Acetoin is used as a food flavoring (in baked goods) and a fragrance. It can be found in apples, butter, yogurt, asparagus, black currants, blackberry, wheat, broccoli, brussels sprouts, cantaloupe. [Wikipedia].

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-2-Acetoin	ChEBI
(R)-3-Hydroxy-2-butanone	ChEBI
(R)-3-Hydroxybutan-2-one	ChEBI
(R)-Dimethylketol	ChEBI

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

(3R)-3-hydroxybutan-2-one

Traditional Name

(R)-acetoin

CAS Registry Number

Not Available

SMILES

C[C@@H](O)C(C)=O

InChI Identifier

InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m1/s1

InChI Key

ROWKJAVDOGWPAT-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetoin (CHEBI:15686 )
Oxygenated hydrocarbons (LMFA12000064 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.66	ALOGPS
logP	-0.14	ChemAxon
logS	0.73	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	22.39 m³·mol⁻¹	ChemAxon
Polarizability	9.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	124.622	32859911
AllCCS	[M+H-H2O]+	120.217	32859911
AllCCS	[M+Na]+	129.92	32859911
AllCCS	[M+NH4]+	128.733	32859911
AllCCS	[M-H]-	125.669	32859911
AllCCS	[M+Na-2H]-	130.326	32859911
AllCCS	[M+HCOO]-	135.45	32859911
DeepCCS	[M+H]+	121.428	30932474
DeepCCS	[M-H]-	119.48	30932474
DeepCCS	[M-2H]-	155.206	30932474
DeepCCS	[M+Na]+	129.801	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Acetoin,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1137.2	Semi standard non polar	33892256
(R)-Acetoin,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1103.3	Standard non polar	33892256
(R)-Acetoin,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C	1025.7	Standard polar	33892256
(R)-Acetoin,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C	1037.8	Semi standard non polar	33892256
(R)-Acetoin,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C	1069.4	Standard non polar	33892256
(R)-Acetoin,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C	1039.2	Standard polar	33892256
(R)-Acetoin,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1553.0	Semi standard non polar	33892256
(R)-Acetoin,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1538.2	Standard non polar	33892256
(R)-Acetoin,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C	1371.1	Standard polar	33892256
(R)-Acetoin,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C	1482.6	Semi standard non polar	33892256
(R)-Acetoin,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C	1516.1	Standard non polar	33892256
(R)-Acetoin,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C	1378.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Acetoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-15ed087808debd745ef9	2016-09-22	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 - (R)-Acetoin 10V, Positive-QTOF	splash10-000i-9000000000-ebb7996f3f82cc069f12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 20V, Positive-QTOF	splash10-0079-9000000000-4043204b04ec3b5823ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 40V, Positive-QTOF	splash10-0uk9-9000000000-1e66901c3375433b1693	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 10V, Negative-QTOF	splash10-000i-9000000000-9d60c7f29d91e72ce0bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 20V, Negative-QTOF	splash10-000i-9000000000-35eb749498333af99296	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 40V, Negative-QTOF	splash10-00xr-9000000000-ce5e7eaa33d4f9d4fa86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 10V, Positive-QTOF	splash10-0fk9-9000000000-c5e178ac425b271910a2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 20V, Positive-QTOF	splash10-0006-9000000000-f43d429661b310e7148a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 40V, Positive-QTOF	splash10-0006-9000000000-160fee6a321df2fa7b05	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 10V, Negative-QTOF	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 20V, Negative-QTOF	splash10-000i-9000000000-bc260446b65990487a67	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Acetoin 40V, Negative-QTOF	splash10-0006-9000000000-0c841ea6edf8e31c3df0	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

DB04364

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008099

KNApSAcK ID

Not Available

Chemspider ID

388445

KEGG Compound ID

C00810

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439314

PDB ID

Not Available

ChEBI ID

15686

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1660331

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (R)-Acetoin (HMDB0303161)

MOL for HMDB0303161 ((R)-Acetoin)

3D MOL for HMDB0303161 ((R)-Acetoin)

3D SDF for HMDB0303161 ((R)-Acetoin)

3D-SDF for HMDB0303161 ((R)-Acetoin)

PDB for HMDB0303161 ((R)-Acetoin)

3D PDB for HMDB0303161 ((R)-Acetoin)

SMILES for HMDB0303161 ((R)-Acetoin)

INCHI for HMDB0303161 ((R)-Acetoin)

Structure for HMDB0303161 ((R)-Acetoin)

3D Structure for HMDB0303161 ((R)-Acetoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra