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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:20 UTC

Update Date

2023-02-21 17:21:58 UTC

HMDB ID

HMDB0032351

Secondary Accession Numbers

HMDB32351

Metabolite Identification

Common Name

Isopropenyl acetate

Description

Isopropenyl acetate, also known as 1-methylvinyl acetate or 1-propen-2-ol, acetate, belongs to the class of organic compounds known as enol esters. These are ester derivatives of enols. They have the general formula RC=COC(=O)R' where R, R' = H or organyl group. Based on a literature review very few articles have been published on Isopropenyl acetate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isopropenyl acetic acid	Generator
1-Acetoxy-1-methylethylene	HMDB
1-Methylvinyl acetate	HMDB
1-Propen-2-ol, 2-acetate	HMDB
1-Propen-2-ol, acetate	HMDB
1-Propen-2-yl acetate	HMDB
2-Acetoxypropene	HMDB
2-Acetoxypropylene	HMDB
Acetic acid 1-methylethenyl ester	HMDB
Acetic acid isopropenyl ester	HMDB
Acetic acid, isopropenyl ester	HMDB
Acetic acid,isopropenyl ester	HMDB
Acetone-enol acetate	HMDB
Isopropenylester kyseliny octove	HMDB
Methylvinyl acetate	HMDB
Propen-2-yl acetate	HMDB
Prop-1-en-2-yl acetic acid	HMDB
Isopropenyl acetate	MeSH

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

prop-1-en-2-yl acetate

Traditional Name

1-propen-2-ol acetate

CAS Registry Number

108-22-5

SMILES

CC(=C)OC(C)=O

InChI Identifier

InChI=1S/C5H8O2/c1-4(2)7-5(3)6/h1H2,2-3H3

InChI Key

HETCEOQFVDFGSY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enol esters. These are ester derivatives of enols. They have the general formula RC=COC(=O)R' where R, R' = H or organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Enol esters

Alternative Parents

Substituents

Enol ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032351)
Cytoplasm (HMDB: HMDB0032351)

Source

Endogenous

Endogenous (HMDB: HMDB0032351)

Exogenous

Food

Food (HMDB: HMDB0032351)

Exogenous (HMDB: HMDB0032351)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-92.9 °C	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
Water Solubility	42.5 g/L	ALOGPS
logP	1.19	ALOGPS
logP	0.5	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.92 m³·mol⁻¹	ChemAxon
Polarizability	10.45 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
DarkChem	[M+H]+	121.55	31661259
DarkChem	[M-H]-	114.517	31661259
DeepCCS	[M+H]+	124.98	30932474
DeepCCS	[M-H]-	123.085	30932474
DeepCCS	[M-2H]-	158.911	30932474
DeepCCS	[M+Na]+	133.377	30932474
AllCCS	[M+H]+	125.1	32859911
AllCCS	[M+H-H2O]+	120.8	32859911
AllCCS	[M+NH4]+	129.1	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	124.1	32859911
AllCCS	[M+Na-2H]-	128.1	32859911
AllCCS	[M+HCOO]-	132.5	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.	3.32 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4162 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1347.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	409.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	260.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	423.5 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	332.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	869.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	310.1 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	1079.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	330.8 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	103.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopropenyl acetate	CC(=C)OC(C)=O	961.5	Standard polar	33892256
Isopropenyl acetate	CC(=C)OC(C)=O	668.2	Standard non polar	33892256
Isopropenyl acetate	CC(=C)OC(C)=O	655.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-128dcfaeaaf8ba85fe02	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-7f1e98b1755aee7accaa	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-abe0e6beac8338461e08	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-7d920a7c76b7d2f86044	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate CI-B (Non-derivatized)	splash10-0fk9-9600000000-8405bd89f3f8ebc574c3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-128dcfaeaaf8ba85fe02	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-7f1e98b1755aee7accaa	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-abe0e6beac8338461e08	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate EI-B (Non-derivatized)	splash10-0006-9000000000-7d920a7c76b7d2f86044	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropenyl acetate CI-B (Non-derivatized)	splash10-0fk9-9600000000-8405bd89f3f8ebc574c3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropenyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-23f07db73c61b849ce48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropenyl 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 - Isopropenyl acetate 10V, Positive-QTOF	splash10-0udi-9800000000-f72e6d6772530c6ea8ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 20V, Positive-QTOF	splash10-0nmi-9100000000-0299e8379f6f2e799a5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 40V, Positive-QTOF	splash10-0006-9000000000-00cf8d7372b3741b8377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 10V, Negative-QTOF	splash10-052b-9000000000-24cf1388f2b9ca285720	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-78bab8352d9983c36844	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-e37f115e33a792ecf923	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 10V, Negative-QTOF	splash10-0a4i-9000000000-529c0a1e1387282bf0c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-fd7418ff8c10607dbbe3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-3d555df017e51a513201	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 10V, Positive-QTOF	splash10-0006-9000000000-3218076b0e684c99087b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 20V, Positive-QTOF	splash10-0006-9000000000-1f62a2ad5eb3e2d575de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropenyl acetate 40V, Positive-QTOF	splash10-000f-9000000000-cadec113aee38f6ecca8	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

FDB009648

KNApSAcK ID

Not Available

Chemspider ID

7628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isopropenyl acetate

METLIN ID

Not Available

PubChem Compound

7916

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Isopropenyl acetate (HMDB0032351)

MOL for HMDB0032351 (Isopropenyl acetate)

3D MOL for HMDB0032351 (Isopropenyl acetate)

3D SDF for HMDB0032351 (Isopropenyl acetate)

3D-SDF for HMDB0032351 (Isopropenyl acetate)

PDB for HMDB0032351 (Isopropenyl acetate)

3D PDB for HMDB0032351 (Isopropenyl acetate)

SMILES for HMDB0032351 (Isopropenyl acetate)

INCHI for HMDB0032351 (Isopropenyl acetate)

Structure for HMDB0032351 (Isopropenyl acetate)

3D Structure for HMDB0032351 (Isopropenyl acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra