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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:23:34 UTC

Update Date

2023-02-21 17:30:02 UTC

HMDB ID

HMDB0060476

Secondary Accession Numbers

HMDB60476

Metabolite Identification

Common Name

epsilon-Caprolactone

Description

ε-Caprolactone, also known simply as caprolactone, is a compound belonging to the family of compounds known as lactones. Lactones are cyclic esters of hydroxyl carboxylic acids, wherein the functional group has become part of a ring structure with carbon atoms. Caprolactone consists of a seven membered ring derived from the cyclization of caproic acid. As a monomer it used in the production of highly specialized plastics and polymers. Caprolactone is produced by the Baeyer-Villiger oxidation of cyclohexanone with peracetic acid, and was used previously (until economically inviable) as a precursor in the production of caprolactam. Several other caprolactone isomers are known. These isomers include α-, β-, γ-, and δ-caprolactones. All are chiral. (R)-γ-caprolactone is a component of floral scents and of the aromas of some fruits and vegetables (Journal of Agricultural and Food Chemistry. 37: 413–418), while δ-caprolactone is found in heated milk fat (Journal of Dairy Science. 48 (5): 615–616).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,6-Hexanolide	ChEBI
1-Oxa-2-oxocycloheptane	ChEBI
2-Oxacycloheptanone	ChEBI
2-Oxepanone	ChEBI
2-Oxohexamethylene oxide	ChEBI
6-Hexanolactone	ChEBI
6-Hexanolide	ChEBI
6-Hydroxyhexanoic acid lactone	ChEBI
6-Hydroxyhexanoic acid, epsilon-lactone	ChEBI
Caprolactone	ChEBI
epsilon-Caprolactone monomer	ChEBI
Hexan-6-olide	ChEBI
Hexanoic acid, epsilon-lactone	ChEBI
Hexano-6-lactone	Kegg
6-Hydroxyhexanoate lactone	Generator
6-Hydroxyhexanoate, epsilon-lactone	Generator
Hexanoate, epsilon-lactone	Generator
epsilon-Captolactamium hydrogen sulfate	HMDB
epsilon-Caprolactone	ChEBI

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

oxepan-2-one

Traditional Name

caprolactone

CAS Registry Number

Not Available

SMILES

O=C1CCCCCO1

InChI Identifier

InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2

InChI Key

PAPBSGBWRJIAAV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Lactone
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

epsilon-lactone (CHEBI:17915 )
a small molecule (CPD-101 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060476)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
Water Solubility	23.2 g/L	ALOGPS
logP	0.51	ALOGPS
logP	1.04	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Basic)	-7	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	29.51 m³·mol⁻¹	ChemAxon
Polarizability	11.99 Å³	ChemAxon
Number of Rings	1	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]+	123.007	31661259
DarkChem	[M-H]-	117.657	31661259
DeepCCS	[M+H]+	130.96	30932474
DeepCCS	[M-H]-	128.841	30932474
DeepCCS	[M-2H]-	164.54	30932474
DeepCCS	[M+Na]+	139.443	30932474
AllCCS	[M+H]+	122.8	32859911
AllCCS	[M+H-H2O]+	117.7	32859911
AllCCS	[M+NH4]+	127.5	32859911
AllCCS	[M+Na]+	128.8	32859911
AllCCS	[M-H]-	123.6	32859911
AllCCS	[M+Na-2H]-	126.1	32859911
AllCCS	[M+HCOO]-	128.9	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.	3.06 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1816 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1673.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	429.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	285.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	429.0 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	521.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1025.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	324.8 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	1028.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.0 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	148.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
epsilon-Caprolactone	O=C1CCCCCO1	1899.1	Standard polar	33892256
epsilon-Caprolactone	O=C1CCCCCO1	1035.9	Standard non polar	33892256
epsilon-Caprolactone	O=C1CCCCCO1	1041.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - epsilon-Caprolactone EI-B (Non-derivatized)	splash10-052f-9000000000-d988c3d2aef36f68a34c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - epsilon-Caprolactone EI-B (Non-derivatized)	splash10-052f-9000000000-d988c3d2aef36f68a34c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - epsilon-Caprolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9000000000-8217d06e4a5254272c26	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - epsilon-Caprolactone 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 - epsilon-Caprolactone 10V, Positive-QTOF	splash10-014i-3900000000-d94e398e2ee123530b4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Positive-QTOF	splash10-014i-9400000000-fc41d0ade3b55f7291c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Positive-QTOF	splash10-0a4l-9000000000-862a975676e9bf4924df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Negative-QTOF	splash10-03di-1900000000-756be03620da7cfbd76f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Negative-QTOF	splash10-03di-8900000000-13e99685e36286d5f0c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Negative-QTOF	splash10-052f-9000000000-5dc62aecedc9db16ddd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Positive-QTOF	splash10-014i-9400000000-f060672f001b0ed52de9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Positive-QTOF	splash10-00xu-9000000000-914e64a3efc4beff8c59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Positive-QTOF	splash10-0a4i-9000000000-59e5dead8150b8ddd28b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 10V, Negative-QTOF	splash10-03di-0900000000-26d0fd1f45832bba1508	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 20V, Negative-QTOF	splash10-03di-7900000000-0a2a806fd9a2f25f9189	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - epsilon-Caprolactone 40V, Negative-QTOF	splash10-0006-9100000000-752185e44397ff541ef7	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01880

BioCyc ID

CPD-101

BiGG ID

Not Available

Wikipedia Link

Caprolactone

METLIN ID

Not Available

PubChem Compound

10401

PDB ID

Not Available

ChEBI ID

17915

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Regucalcin

General function:: Involved in calcium ion binding
Specific function:: Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:: RGN
Uniprot ID:: Q15493
Molecular weight:: 33252.53

Reactions

epsilon-Caprolactone + Water → 6-Hydroxyhexanoic acid	details

Showing metabocard for epsilon-Caprolactone (HMDB0060476)

MOL for HMDB0060476 (epsilon-Caprolactone)

3D MOL for HMDB0060476 (epsilon-Caprolactone)

3D SDF for HMDB0060476 (epsilon-Caprolactone)

3D-SDF for HMDB0060476 (epsilon-Caprolactone)

PDB for HMDB0060476 (epsilon-Caprolactone)

3D PDB for HMDB0060476 (epsilon-Caprolactone)

SMILES for HMDB0060476 (epsilon-Caprolactone)

INCHI for HMDB0060476 (epsilon-Caprolactone)

Structure for HMDB0060476 (epsilon-Caprolactone)

3D Structure for HMDB0060476 (epsilon-Caprolactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions