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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:47:22 UTC

Update Date

2023-02-21 17:25:27 UTC

HMDB ID

HMDB0036626

Secondary Accession Numbers

HMDB36626

Metabolite Identification

Common Name

3,4-Dihydro-2H-1-benzopyran-2-one

Description

3,4-Dihydro-2H-1-benzopyran-2-one, also known as 3,4-dihydrocoumarin or 1,2-benzodihydropyrone, belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position. 3,4-Dihydro-2H-1-benzopyran-2-one exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydro-2H-1-benzopyran-2-one is a sweet, almond, and cinnamon tasting compound. 3,4-Dihydro-2H-1-benzopyran-2-one has been detected, but not quantified, in several different foods, such as green vegetables, pulses, sour cherries, and tarragons. A chromanone that is the 3,4-dihydro derivative of coumarin.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Benzodihydropyrone	ChEBI
2-Hydroxydihydrocinnamic acid lactone	ChEBI
3,4-Dihydro-2H-chromen-2-one	ChEBI
Benzodihydropyrone	ChEBI
Dihydrocoumarin	ChEBI
Hydrocoumarin	ChEBI
Melilotic acid lactone	ChEBI
Melilotic lactone	ChEBI
Melilotin	ChEBI
Melilotol	ChEBI
O-Hydroxydihydrocinnamic acid lactone	ChEBI
O-Hydroxyhydrocinnamic acid delta-lactone	ChEBI
3,4-Dihydrocoumarin	Kegg
2-Hydroxydihydrocinnamate lactone	Generator
Melilotate lactone	Generator
O-Hydroxydihydrocinnamate lactone	Generator
O-Hydroxyhydrocinnamate delta-lactone	Generator
O-Hydroxyhydrocinnamate δ-lactone	Generator
O-Hydroxyhydrocinnamic acid δ-lactone	Generator
2-Hydroxyhydrocinnamic lactone	HMDB
3,4-dihydro-1-Benzopyran-2-one	HMDB
3,4-dihydro-Coumarin	HMDB
3,4-Dihydroxycoumarin	HMDB
dihydro-Benzopyranone	HMDB
FEMA 2381	HMDB
Hydrocinnamic acid, O-hydroxy-, delta-lactone	HMDB
Hydrocoumarin, 8ci	HMDB
Melilotin (coumarin)	HMDB
Melilotin??	HMDB
O-Hydroxyhydrocinnamic acid lactone	HMDB

Chemical Formula

C₉H₈O₂

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

IUPAC Name

3,4-dihydro-2H-1-benzopyran-2-one

Traditional Name

dihydrocoumarin

CAS Registry Number

119-84-6

SMILES

O=C1CCC2=CC=CC=C2O1

InChI Identifier

InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2

InChI Key

VMUXSMXIQBNMGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

3,4-dihydrocoumarins

Sub Class

Not Available

Direct Parent

3,4-dihydrocoumarins

Alternative Parents

Substituents

3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Benzenoid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromanone (CHEBI:16151 )
an aromatic compound (DIHYDROCOUMARIN )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036626)
Cytoplasm (HMDB: HMDB0036626)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036626)

Source

Exogenous

Food

Food (HMDB: HMDB0036626)

Herb and spice

Herb

Tarragon (FooDB: FOOD00019)

Fruit

Drupe

Sour cherry (FooDB: FOOD00146)

Pulse

Pulses (FooDB: FOOD00867)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0036626)
Fabaceae (HMDB: HMDB0036626)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036626)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0036626)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0036626)
Flavoring Agent (HMDB: HMDB0036626)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	25 °C	Not Available
Boiling Point	271.00 to 272.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3 mg/mL at 37 °C	Not Available
LogP	2.428 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.25 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.89	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-7.2	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	0	ChemAxon
Refractivity	40.46 m³·mol⁻¹	ChemAxon
Polarizability	15.09 Å³	ChemAxon
Number of Rings	2	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]+	132.567	31661259
DarkChem	[M-H]-	128.218	31661259
DeepCCS	[M+H]+	129.828	30932474
DeepCCS	[M-H]-	126.565	30932474
DeepCCS	[M-2H]-	163.746	30932474
DeepCCS	[M+Na]+	138.709	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	125.6	32859911
AllCCS	[M+NH4]+	134.8	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	130.3	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-2H-1-benzopyran-2-one	O=C1CCC2=CC=CC=C2O1	2488.3	Standard polar	33892256
3,4-Dihydro-2H-1-benzopyran-2-one	O=C1CCC2=CC=CC=C2O1	1309.5	Standard non polar	33892256
3,4-Dihydro-2H-1-benzopyran-2-one	O=C1CCC2=CC=CC=C2O1	1383.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one EI-B (Non-derivatized)	splash10-0ffw-9500000000-19f4cacfc3593f445e42	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-3a0260eb973faa6f27df	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)	splash10-02du-2900000000-0780738b649dc11f75a4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one EI-B (Non-derivatized)	splash10-0ffw-9500000000-19f4cacfc3593f445e42	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-3a0260eb973faa6f27df	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)	splash10-02du-2900000000-0780738b649dc11f75a4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fka-2900000000-071c9c2781c319fe04bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006w-8900000000-1c291ea2d1c34d7a5a68	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOF	splash10-0002-0900000000-4aa1a496f0327462d05e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-bacf3cdab2c00f9d3a52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-c86ad9f3b77d06e78084	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-0a4i-0900000000-1a9803adbe959ab8c397	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 30V, Positive-QTOF	splash10-0a4i-0900000000-c86ad9f3b77d06e78084	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-0002-0900000000-4aa1a496f0327462d05e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 35V, Negative-QTOF	splash10-014i-0900000000-e00f4063d413008ffe40	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-0a4i-0900000000-bacf3cdab2c00f9d3a52	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-0002-0900000000-1a2460bc4ea458349c97	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-0a4j-0900000000-9cfc6b98409c1ab92b17	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0pb9-8900000000-4d6bcd5ccd07a0beeb52	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-0002-0900000000-f2275d03bd7d08c74531	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-0f6t-0900000000-bcc997cb9c43e840687c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-0f6x-9600000000-5eebf3f0198d365245af	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOF	splash10-0002-0900000000-c273ad6f431d1239485b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOF	splash10-0592-1900000000-c7524399be04f94a7e32	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0fb9-9400000000-364ed3e27ac756fed7b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Negative-QTOF	splash10-0002-0900000000-a4c75ebd26f0ac23a7eb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Negative-QTOF	splash10-014j-1900000000-107b906f2798b3915190	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Negative-QTOF	splash10-00vl-6900000000-6809bdcaa3f757b499af	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

660

PDB ID

Not Available

ChEBI ID

16151

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001531

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 3,4-Dihydro-2H-1-benzopyran-2-one (HMDB0036626)

MOL for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

3D MOL for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

3D SDF for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

3D-SDF for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

PDB for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

3D PDB for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

SMILES for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

INCHI for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

Structure for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

3D Structure for HMDB0036626 (3,4-Dihydro-2H-1-benzopyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra